HHH

The following discussion and analysis by management should be read in conjunction with the unaudited Condensed Consolidated Financial Statements and Notes included in this Quarterly Report on Form 10-Q and with the audited Consolidated Financial Statements included in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025, filed with the SEC on February 19, 2026. All references to numbered Notes are to specific notes to our unaudited Condensed Consolidated Financial Statements included in this Quarterly Report. Capitalized terms used, but not defined, in this MD&A have the same meanings as in such Notes. Throughout this section, changes for monetary amounts between periods presented are calculated based on the amounts in thousands of dollars stated in our condensed consolidated financial statements and then rounded to the nearest million. Therefore, certain changes may not recalculate based on the amounts rounded to the nearest million. Index Page Forward-Looking Information 47 Overview 49 Results of Operations 51 Operating Assets 52 Master Planned Communities 54 Strategic Developments 57 Corporate Income, Expenses, and Other Items 59 Liquidity and Capital Resources 62 Critical Accounting Policies and Estimates 66 HHH 2026 FORM 10-Q | 46 MANAGEMENT’S DISCUSSION AND ANALYSIS Table of Contents FORWARD-LOOKING INFORMATION This Quarterly Report on Form 10-Q (Quarterly Report) contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 (Exchange Act). We intend these statements to be covered by the safe harbor for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995. Forward-looking statements give our current expectations relating to our financial condition, results of operations, plans, objectives, future performance, or business, and are not guarantees of performance. These statements may include words such as “anticipate,” “believe,” “estimate,” “expect,” “forecast,” “intend,” “likely,” “may,” “plan,” “project,” “realize,” “should,” “transform,” “will,” “would,” and other statements of similar expression. Forward-looking statements should not be relied upon, and actual results may differ materially from those contemplated by such forward-looking statements. Forward-looking statements include statements regarding: – the changes to our strategy following the closing of the May 2025 transactions with Pershing Square – accelerated growth in our core Master Planned Communities assets – expected performance of our stabilized, income-producing properties, and the performance and stabilization timing of properties that we have recently placed into service or are under construction – forecasts of our future economic performance – expected capital required for our operations and development opportunities for our properties – planned and recently-completed acquisitions, including the acquisition of Vantage Group Holdings Ltd. (Vantage), and our ability to integrate and realize the economic benefits of acquired businesses – impact of technology on our operations and business – expected performance of our segments – expected commencement and completion for property developments and timing of sales or rentals of certain properties – risks related to our insurance and reinsurance business, including underwriting, reserving, catastrophe, reinsurance, capital, liquidity, and regulatory risks – estimates of our future liquidity, development opportunities, development spending, and management plans; and – descriptions of assumptions underlying or relating to any of the foregoing These statements involve known and unknown risks, uncertainties, and other factors that may cause our actual results, performance, and achievements to materially differ from any future results, performance and achievements expressed or implied by such forward-looking statements. Factors that could cause actual results to differ materially from those expressed or implied by the forward-looking statements include: –our ability to realize the anticipated benefits of the transactions with Pershing Square and our strategy of becoming a diversified holding company –our ability to identify and consummate transactions as part of our strategy of becoming a diversified holding company –risks inherent in acquiring or making investments in operating companies, especially companies in industries unrelated to our existing real estate business –our ability to integrate Vantage’s insurance and reinsurance business into our operations, and realize the financial and strategic benefits currently anticipated from such acquisition –our ability to realize the anticipated benefits of recent transactions, including the May 2025 transactions with Pershing Square and the spinoff of Seaport Entertainment Group Inc. in 2024 –macroeconomic conditions such as volatility in capital markets, unstable economic and political conditions within the U.S. and foreign jurisdictions, geopolitical conflicts, and a prolonged recession in the national economy impacting the real estate and insurance and reinsurance businesses, including but not limited to inflation and changes in interest rates –changes in trade policies, including tariffs, and related impacts on market conditions and business activity –our inability to obtain operating and development capital for our properties, including our inability to obtain or refinance debt capital from lenders and the capital markets –our ability to compete effectively, including the potential impact of heightened competition for tenants and potential decreases in occupancy at our properties –extreme weather conditions, climate change, natural disasters, pandemics or other catastrophes, that may cause property damage or interrupt our real estate or insurance or reinsurance business –losses that are not insured or exceed the applicable insurance limits as well as insufficient reserves for losses –increased construction costs exceeding our original estimates, delays or overruns, claims for construction defects, or other factors affecting our ability to develop, redevelop or construct our properties HHH 2026 FORM 10-Q | 47 MANAGEMENT’S DISCUSSION AND ANALYSIS Table of Contents –regulation of the portions of our business that are dedicated to the formation and sale of condominiums or insurance and reinsurance, as applicable, including obtaining government permits necessary for the development of our properties –fluctuations in regional and local economies, the impact of changes in interest rates on residential housing and condominium markets, local real estate conditions, tenant rental rates, and competition from competing retail properties and the internet –insufficient reserves for insurance claims and claim expenses due to the impact of social inflation or other factors –greater-than-expected loss ratios on business written by Vantage –Vantage’s ability to accurately assess underwriting risk and establish adequate premium rates –decreases in pricing for property and casualty reinsurance and insurance –Vantage’s ability to purchase adequate reinsurance –Vantage’s ability to maintain financial strength ratings –material variation of analytical models used in decision making from actual results –Vantage’s ability to comply with insurance and tax laws and regulations and other regulatory challenges, including to obtain licenses or admittance in additional jurisdictions to develop its business; –inherent risks related to disruption of information technology networks and related systems, including cyber security attacks on us or our vendors –our indebtedness, including our $650,000,000 4.125% senior unsecured notes due 2029, $650,000,000 4.375% senior unsecured notes due 2031, $500,000,000 5.875% senior unsecured notes due 2032, and $500,000,000 6.125% senior unsecured notes due 2034, contain restrictions that may limit our ability to operate our business –our directors’ involvement or interests in other businesses, including real estate activities and investments –our dependence on the operations and funds of our subsidiaries, including The Howard Hughes Corporation and Vantage; and –other risks and uncertainties described herein, as well as those risks and uncertainties discussed from time to time in our other reports and other public filings with the SEC, including the Company’s Annual Report on Form 10-K for the year ended December 31, 2025. The above list of risks and uncertainties is only a summary of some of the most important factors and is not intended to be exhaustive. Any factor could, by itself, or together with one or more other factors, adversely affect our business, results of operations, plans, objectives, future performance, or financial condition. Other factors not described in this Quarterly Report also could cause results to differ from our expectations. Given these uncertainties, we caution you not to place undue reliance on these forward-looking statements. We undertake no obligation to update or revise any of our forward-looking statements for events or circumstances that arise after the statement is made, except as otherwise may be required by law. HHH 2026 FORM 10-Q | 48 MANAGEMENT’S DISCUSSION AND ANALYSISOVERVIEW Table of Contents OVERVIEW Description of Business Overview Howard Hughes Holdings Inc. (HHH or the Company) is a holding company that owns subsidiaries engaged in various diverse business activities. These include a real estate development subsidiary that operates a large-scale, mixed-use real estate platform focused on the development of master planned communities (MPCs), the investment in strategic real estate development opportunities, and the ownership and operation of income-producing properties, and a specialty insurance and reinsurance subsidiary, which provides property, casualty, and specialty insurance and reinsurance. Vantage Acquisition On June 4, 2026, Howard Hughes Insurance Holdings, LLC, a wholly owned subsidiary of the Company, completed the acquisition of 100% of the outstanding shares of capital stock of Vantage Group Holdings, Ltd., a privately held specialty insurance and reinsurance company, for cash consideration of approximately $2.1 billion (Vantage Acquisition). References to "Vantage" herein refer to Howard Hughes Insurance Holdings, LLC and its consolidated insurance and reinsurance subsidiaries acquired in the Vantage Acquisition, unless the context otherwise requires. Also on June 4, 2026, to support the funding of the Vantage Acquisition, the Company issued $1.0 billion of its Series A Preferred Stock to Pershing Square Holdings, Ltd. See Note 2 - Vantage Acquisition and Note 3 - Pershing Square in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. The accompanying Condensed Consolidated Financial Statements reflect the assets acquired, liabilities assumed, and results of operations of Vantage beginning on the acquisition date. Accordingly, the Company's results for the three and six months ended June 30, 2026 include Vantage's results only for the period subsequent to the acquisition date. Vantage operates in the United States (U.S.) and Bermuda. Vantage writes insurance business in the U.S. on both an admitted and excess and surplus basis, and writes specialty insurance and reinsurance business in Bermuda on a worldwide basis. Insurance product lines offered by its U.S. insurance subsidiaries include casualty, property, professional liability, financial lines, healthcare, construction, and political risk and credit. Insurance products offered by its Bermuda subsidiary include financial and professional lines and healthcare and excess casualty. Vantage’s reinsurance operations include specialty, property and casualty, financial lines, and property catastrophe. Vantage also earns net investment income and net fee income. The acquisition diversifies our portfolio and is expected to provide recurring premium and fee-based revenues and investment income over time. Segments Due to the recent timing of the Vantage Acquisition, the Company is continuing to evaluate the acquired operations, including the manner in which the chief operating decision maker reviews financial information and allocates resources. Accordingly, the results of the acquired business have not yet been separately reflected within the Company’s segment reporting disclosures as of June 30, 2026. The Company expects to finalize its segment reporting assessment as integration activities progress. We have separately disclosed the impact of Vantage on consolidated results below to enable investors to understand the contribution of the acquisition to the period. We continue to operate through three business segments: Operating Assets, MPCs, and Strategic Developments. In our MPC segment, we plan, develop, and manage small cities and large-scale, mixed-use communities, in markets with strong long-term growth fundamentals. This business focuses on the horizontal development of residential land. The improved acreage is then sold to homebuilders who build and sell homes to new residents. New homeowners create demand for commercial developments, such as retail, office, and hospitality offerings. We build these commercial properties through Strategic Developments at the appropriate times, which helps mitigate development risk, using the cash flow harvested from the sale of land to homebuilders. Once the commercial developments are completed, the assets transition to Operating Assets, which increases recurring Net Operating Income (NOI). New office, retail, and other commercial amenities make our MPC residential land more appealing to buyers and increase the velocity of land sales at premiums that typically exceed the broader market and generate more cash flow from MPCs. Our Strategic Developments segment also develops and sells residential condominiums in Hawai‘i. Non-GAAP Measures In addition to the required presentations using GAAP, we use certain non-GAAP performance measures, such as NOI and Net Debt. See the Operating Assets and Short- and Long-Term Liquidity sections below for the reconciliations of these non-GAAP to GAAP financial measures and statements indicating why management believes these non-GAAP financial measures provide useful information for investors. HHH 2026 FORM 10-Q | 49 MANAGEMENT’S DISCUSSION AND ANALYSISOVERVIEW Table of Contents Second Quarter 2026 Highlights Comparison of the three months ended June 30, 2026, to the three months ended June 30, 2025 Total Company –Net income attributable to common stockholders increased to income of $158.4 million in the current quarter, compared to a loss of $12.1 million in the prior-year period. This increase was primarily driven by condominium sales at The Park Ward Village, gains on the sale of two multifamily properties in the current period, and an increase in MPC EBT attributable to changes in deferred revenue and an increase in residential land sales closed in Summerlin. These increases were partially offset by a net loss attributable to Vantage following the completion of the Vantage Acquisition in the current period. –We continue to maintain a strong liquidity position with $2.6 billion of cash and cash equivalents, including cash held at Vantage, $515.0 million of undrawn capacity on our Secured Bridgeland Notes, $970.3 million of undrawn lender commitments available to be drawn for property development, subject to certain restrictions, and limited near-term debt maturities, all as of June 30, 2026. Operating Assets –Operating Assets NOI totaled $68.5 million in the current quarter, a $1.6 million increase compared to $66.9 million in the prior-year period. –Operating Assets results reflect modest increases across all property types driven by strong leasing activity and expiration of rent abatements. –In the second quarter of 2026, the Company completed the sale of two multifamily properties in The Woodlands, resulting in a gain of $51.8 million. MPC –MPC EBT totaled $134.7 million in the current quarter, a $32.3 million increase compared to $102.4 million in the prior-year period. –The increase in EBT was primarily due to changes in deferred revenue, net of associated deferred costs, an increase in SID bond assumptions, and residential MPC land sales closed in Summerlin. Strategic Developments –Strategic Developments EBT totaled $126.6 million in the current quarter, a $125.6 million increase compared to $1.0 million in the prior-year period. –The increase in EBT was primarily due to the closing of 527 units at The Park Ward Village in the current quarter. Corporate Income, Expenses, and Other Items –Corporate income, expenses, and other items, excluding the Vantage pre-tax net loss discussed below, included an increase in net expenses of $8.8 million primarily due to an increase in income tax expense and a net increase in general and administrative expenses, primarily related to Vantage Acquisition transaction costs, partially offset by a decrease in compensation and benefit costs related to the strategic reduction in force in 2025. These increases in expenses were partially offset by a reduction in loss on sale of MUD receivables. –Net income includes a pre-tax net loss of $20.8 million related to the post-acquisition activity of Vantage. This includes a net investment loss of $38.3 million, primarily attributable to unrealized losses on equity securities and realized losses on the sale of fixed maturity securities. Without the impact of the net investment loss, Vantage generated pre-tax net income of $17.5 million in the post-acquisition period. Refer to the Vantage Post-Acquisition Results section below for further discussion of this activity. HHH 2026 FORM 10-Q | 50 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents RESULTS OF OPERATIONS Comparison of the six months ended June 30, 2026, to the six months ended June 30, 2025 Net income attributable to common stockholders increased $168.2 million to $166.6 million in the six months ended June 30, 2026, compared to a loss of $1.6 million in the prior-year period. –Strategic Developments EBT increased $120.2 million, primarily due to the closing of condominium units at The Park Ward Village in the current period, partially offset by a decrease in equity earnings related to the recognition of the Company’s share of a loss on sale of land at our West End Alexandria joint venture. –MPC EBT increased $53.4 million, primarily due to changes in deferred revenue, net of associated deferred costs and an increase in SID bond assumptions in Summerlin, increases in residential MPC land sales closed in Bridgeland and The Woodlands Hills, and increases in commercial MPC land sales closed in The Woodlands and Bridgeland. –Operating Assets EBT increased $33.5 million primarily due to an increase in gain on sale of real estate and an increase in rental revenues, net of operating costs due to increased leasing activity across our portfolio, partially offset by an increase in depreciation and amortization. –Net income includes a pre-tax net loss of $20.8 million related to the post-acquisition activity of Vantage. This includes a net investment loss of $38.3 million, primarily attributable to unrealized losses on equity securities and realized losses on the sale of fixed maturity securities. Without the impact of the net investment loss, Vantage generated pre-tax net income of $17.5 million in the post-acquisition period. Refer to the Vantage Post-Acquisition Results section below for further discussion of this activity. –Corporate income, expenses, and other items, excluding the Vantage pre-tax net loss discussed above, included an increase in net expenses of $20.0 million, primarily due to an increase in income tax expense, recognition of a loss on extinguishment of debt, and a net increase in general and administrative expenses, primarily related to Vantage Acquisition transaction costs and Pershing Square advisory fees, partially offset by a decrease in compensation and benefit costs related to the strategic reduction in force in 2025. These increases in expenses were partially offset by a reduction in loss on sale of MUD receivables. Refer to the Second Quarter 2026 Highlights section above for information on the variances for the three months ended June 30, 2026. See segment discussions for more detail about the changes described above. HHH 2026 FORM 10-Q | 51 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents Operating Assets Segment EBT Segment EBT for Operating Assets is presented below: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Rental revenue $ 114,200 $ 111,118 $ 3,082 3 % $ 227,749 $ 219,472 $ 8,277 4 % Other revenues 5,760 5,328 432 8 % 11,413 10,976 437 4 % Total revenues 119,960 116,446 3,514 3 % 239,162 230,448 8,714 4 % Operating costs (36,104) (34,175) (1,929) (6) % (71,381) (68,397) (2,984) (4) % Rental property real estate taxes (14,293) (14,750) 457 3 % (30,000) (29,501) (499) (2) % (Provision for) recovery of doubtful accounts (123) (542) 419 77 % (64) (386) 322 83 % Total operating expenses (50,520) (49,467) (1,053) (2) % (101,445) (98,284) (3,161) (3) % Segment operating income (loss) 69,440 66,979 2,461 4 % 137,717 132,164 5,553 4 % Depreciation and amortization (52,028) (42,305) (9,723) (23) % (97,606) (85,428) (12,178) (14) % Interest income (expense), net (37,873) (34,173) (3,700) (11) % (71,380) (68,391) (2,989) (4) % Other income (loss), net (527) 634 (1,161) (183) % (508) 438 (946) NM Equity in earnings (losses) from unconsolidated ventures 794 (325) 1,119 NM 6,671 4,318 2,353 54 % Gain (loss) on sale or disposal of real estate and other assets, net 51,800 (1) 51,801 NM 51,800 9,978 41,822 NM Gain (loss) on extinguishment of debt (413) (307) (106) (35) % (413) (307) (106) (35) % Segment EBT $ 31,193 $ (9,498) $ 40,691 NM $ 26,281 $ (7,228) $ 33,509 NM NM Not meaningful. For the three months ended June 30, 2026: Operating Assets segment EBT increased $40.7 million compared to the prior-year period primarily due to the following: –Gain on sale of real estate increased $51.8 million primarily due to the sale of two multifamily properties in The Woodlands in 2026. This increase to EBT was partially offset by the following: –Depreciation and amortization increased $9.7 million primarily due to accelerated depreciation of a Ward Village retail property which was decommissioned in the current quarter to allow for the construction of future condo towers. For the six months ended June 30, 2026: Operating Assets segment EBT increased $33.5 million compared to the prior-year period primarily due to the following: –Gain on sale of real estate increased $41.8 million primarily due to the sale of two multifamily properties in The Woodlands in 2026, compared to the sale of two land parcels and a retail space in Ward Village in 2025. –Rental revenues, net of Operating costs increased $5.3 million primarily due to increased leasing activity across our portfolio and expiration of rent abatements. These increases to EBT were partially offset by the following: –Depreciation and amortization increased $12.2 million primarily due to accelerated depreciation of a Ward Village retail property which was decommissioned in the current quarter to allow for the construction of future condo towers. Net Operating Income In addition to the required presentations using GAAP, we use certain non-GAAP performance measures, as we believe these measures improve the understanding of our operational results and make comparisons of operating results among peer companies more meaningful. Management continually evaluates the usefulness, relevance, limitations and calculation of our reported non-GAAP performance measures to determine how best to provide relevant information to the public, and thus such reported measures could change. HHH 2026 FORM 10-Q | 52 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents We define NOI as operating revenues (rental income, tenant recoveries, and other revenue) less operating expenses (real estate taxes, repairs and maintenance, marketing, and other property expenses). NOI excludes straight-line rents and amortization of tenant incentives, net; interest expense, net; ground rent amortization; demolition costs; other income (loss); depreciation and amortization; development-related marketing costs; gain on sale or disposal of real estate and other assets, net; loss on extinguishment of debt; provision for impairment; and equity in earnings from unconsolidated ventures. We believe that NOI is a useful supplemental measure of the performance of our Operating Assets segment because it provides a performance measure that reflects the revenues and expenses directly associated with owning and operating real estate properties. We use NOI to evaluate our operating performance on a property-by-property basis because NOI allows us to evaluate the impact that property-specific factors such as rental and occupancy rates, tenant mix, and operating costs have on our operating results, gross margins, and investment returns. A reconciliation of Operating Assets segment EBT to Operating Assets NOI is presented in the table below. Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Operating Assets segment EBT $ 31,193 $ (9,498) $ 40,691 NM $ 26,281 $ (7,228) $ 33,509 NM Add back: Depreciation and amortization 52,028 42,305 9,723 23 % 97,606 85,428 12,178 14 % Interest (income) expense, net 37,873 34,173 3,700 11 % 71,380 68,391 2,989 4 % Equity in (earnings) losses from unconsolidated ventures (794) 325 (1,119) NM (6,671) (4,318) (2,353) (54) % (Gain) loss on sale or disposal of real estate and other assets, net (51,800) 1 (51,801) NM (51,800) (9,978) (41,822) NM (Gain) loss on extinguishment of debt 413 307 106 35 % 413 307 106 35 % Impact of straight-line rent (1,015) (373) (642) (172) % (3,637) (1,533) (2,104) (137) % Other 600 (384) 984 NM 585 (195) 780 NM Operating Assets NOI $ 68,498 $ 66,856 $ 1,642 2 % $ 134,157 $ 130,874 $ 3,283 3 % NM Not meaningful. The table below presents Operating Assets NOI by property type: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Office $ 36,165 $ 35,159 $ 1,006 3 % $ 69,877 $ 68,062 $ 1,815 3 % Retail 13,890 13,394 496 4 % 27,854 27,204 650 2 % Multifamily 15,557 15,264 293 2 % 30,255 29,259 996 3 % Other 1,713 1,431 282 20 % 3,408 2,973 435 15 % Dispositions (a) 1,173 1,608 (435) (27) % 2,763 3,376 (613) (18) % Operating Assets NOI $ 68,498 $ 66,856 $ 1,642 2 % $ 134,157 $ 130,874 $ 3,283 3 % (a)Properties that were sold are shown separately for all periods presented. Operating Assets NOI increased $1.6 million for the three months ended June 30, 2026, and $3.3 million for the six months ended June 30, 2026, compared to the prior-year periods with modest increases across all property types primarily driven by strong leasing activity and expiration of rent abatements. HHH 2026 FORM 10-Q | 53 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents Master Planned Communities Segment EBT The following table presents segment EBT for MPC: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Master Planned Communities land sales $ 170,936 $ 125,041 $ 45,895 37 % $ 270,509 $ 196,683 $ 73,826 38 % Builder price participation 6,868 14,138 (7,270) (51) % 15,550 23,425 (7,875) (34) % Other revenues 3,936 4,522 (586) (13) % 7,962 8,047 (85) (1) % Total revenues 181,740 143,701 38,039 26 % 294,021 228,155 65,866 29 % Master Planned Communities cost of sales (59,057) (45,178) (13,879) (31) % (93,799) (70,392) (23,407) (33) % Operating costs (11,333) (12,516) 1,183 9 % (24,468) (25,507) 1,039 4 % Total operating expenses (70,390) (57,694) (12,696) (22) % (118,267) (95,899) (22,368) (23) % Segment operating income (loss) 111,350 86,007 25,343 29 % 175,754 132,256 43,498 33 % Depreciation and amortization (110) (88) (22) (25) % (175) (199) 24 12 % Interest income (expense), net 24,012 18,107 5,905 33 % 45,724 34,893 10,831 31 % Other income (loss), net — 35 (35) (100) % 1,860 35 1,825 NM Equity in earnings (losses) from unconsolidated ventures (569) (1,649) 1,080 65 % (4,104) (5,059) 955 19 % Gain (loss) on sale or disposal of real estate and other assets, net — — — NM — 3,750 (3,750) (100) % Segment EBT $ 134,683 $ 102,412 $ 32,271 32 % $ 219,059 $ 165,676 $ 53,383 32 % NM Not meaningful. The following table presents MPC segment EBT by MPC: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Bridgeland $ 23,244 $ 21,371 $ 1,873 9 % $ 57,978 $ 38,163 $ 19,815 52 % Summerlin 107,896 83,235 24,661 30 % 157,309 125,324 31,985 26 % Teravalis (1,588) (1,820) 232 13 % (5,039) (734) (4,305) NM The Woodlands 72 (2,309) 2,381 103 % 852 (1,087) 1,939 178 % The Woodlands Hills 5,059 1,935 3,124 161 % 7,959 4,010 3,949 98 % Segment EBT $ 134,683 $ 102,412 $ 32,271 32 % $ 219,059 $ 165,676 $ 53,383 32 % NM Not meaningful. For the three months ended June 30, 2026: MPC segment EBT increased $32.3 million compared to the prior-year period primarily due to the following: –MPC sales, net of MPC cost of sales increased $32.0 million primarily due to increases in Summerlin related to changes in deferred revenue, net of associated deferred costs, an increase in SID bond assumptions, and an increase in residential MPC land sales, as well as an increase in residential MPC land sales closed in The Woodlands Hills. See Master Planned Communities Land Sales and Residential and Commercial Land Sales Closed tables below for additional information on land sales activity in the period. –Interest income increased $5.9 million primarily due to increased capitalized interest in Bridgeland and Summerlin. –Builder price participation decreased $7.3 million as fewer homes were closed with sales prices over the predetermined breakpoint necessary for participation revenue, primarily in Summerlin. HHH 2026 FORM 10-Q | 54 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents For the six months ended June 30, 2026: MPC segment EBT increased $53.4 million compared to the prior-year period primarily due to the following: –MPC sales, net of MPC cost of sales increased $50.4 million primarily due to increases in Summerlin related to changes in deferred revenue, net of associated deferred costs and an increase in SID bond assumptions, as well as an increase in residential MPC land sales closed in Bridgeland and The Woodlands Hills, and increases in commercial MPC land sales closed in The Woodlands and Bridgeland. –Interest income increased $10.8 million primarily due to increased capitalized interest in Bridgeland and Summerlin. –Builder price participation decreased $7.9 million as fewer homes were closed with sales prices over the predetermined breakpoint necessary for participation revenue, primarily in Summerlin and Bridgeland. Master Planned Communities Land Sales The following table presents the detail of MPC land sales recognized for the three and six months ended June 30, 2026 and 2025. Total net recognized (deferred) revenue includes revenues recognized in the current period which are related to sales closed in prior periods, offset by revenues deferred on sales closed in the current period. Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Total residential land sales closed $ 156,701 $ 149,148 $ 7,553 5 % $ 242,334 $ 218,730 $ 23,604 11 % Total commercial land sales closed 5,426 — 5,426 NM 8,983 — 8,983 NM Net recognized (deferred) revenue: Bridgeland 681 1,064 (383) (36) % 921 1,376 (455) (33) % The Woodlands 102 — 102 NM 440 21 419 NM The Woodlands Hills — — — NM 15 — 15 NM Summerlin 713 (25,333) 26,046 103 % 9,068 (26,151) 35,219 135 % Total net recognized (deferred) revenue 1,496 (24,269) 25,765 106 % 10,444 (24,754) 35,198 142 % Special Improvement District revenue 7,313 162 7,151 NM 8,748 2,707 6,041 NM Master Planned Communities land sales $ 170,936 $ 125,041 $ 45,895 37 % $ 270,509 $ 196,683 $ 73,826 38 % NM Not meaningful. HHH 2026 FORM 10-Q | 55 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents Residential and Commercial Land Sales Closed The following tables detail our residential and commercial land sales closed for the three and six months ended June 30, 2026 and 2025: Three Months Ended June 30, Land Sales Acres Sold Average Price Per Acre thousands except acres sold 2026 2025 2026 2025 2026 2025 Residential Land Sales Closed Bridgeland Single family $ 22,683 $ 26,121 30.2 40.3 $ 751 $ 648 Summerlin Superpad sites 126,069 106,433 73.1 64.6 1,725 1,648 Custom lots — 14,700 — 1.9 — 7,737 The Woodlands Hills Single family 7,949 1,894 16.4 3.7 485 512 Total residential land sales closed (a) $ 156,701 $ 149,148 119.7 110.5 $ 1,309 $ 1,350 Commercial Land Sales Closed Bridgeland $ 2,176 $ — 2.0 — $ 1,088 $ — The Woodlands 3,250 — 2.0 — 1,625 — Total commercial land sales closed (a) $ 5,426 $ — 4.0 — $ 1,357 $ — Six Months Ended June 30, Land Sales Acres Sold Average Price Per Acre thousands except acres sold 2026 2025 2026 2025 2026 2025 Residential Land Sales Closed Bridgeland Single family $ 65,241 $ 48,489 92.1 77.3 $ 708 $ 627 Summerlin Superpad sites 148,469 151,856 85.9 94.0 1,728 1,615 Custom lots 15,750 14,700 2.2 1.9 7,159 7,737 The Woodlands Hills Single family 12,874 3,685 26.5 7.5 486 491 Total residential land sales closed (a) $ 242,334 $ 218,730 206.7 180.7 $ 1,172 $ 1,210 Commercial Land Sales Closed Bridgeland $ 2,176 $ — 2.0 — $ 1,088 $ — The Woodlands 6,807 — 7.8 — 873 — Total commercial land sales closed (a) $ 8,983 $ — 9.8 — $ 917 $ — (a)Excludes revenues recognized in the current period which are related to sales closed in prior periods and includes revenues deferred on sales closed in the current period. Please see the summary of MPC land sales table above which reconciles total residential and commercial land sales closed to MPC land sales revenue recognized for the three and six months ended June 30, 2026 and 2025. HHH 2026 FORM 10-Q | 56 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents MPC Land Inventory The following table summarizes MPC land inventory activity for the six months ended June 30, 2026: thousands Bridgeland Summerlin Teravalis The Woodlands The Woodlands Hills Total MPC Balance December 31, 2025 $ 522,231 $ 1,257,053 $ 547,211 $ 187,315 $ 121,267 $ 2,635,077 Development expenditures (a) 138,789 112,881 1,339 1,828 19,459 274,296 MPC Cost of sales (23,795) (62,893) — (1,878) (5,233) (93,799) MUD reimbursable costs (b) (116,571) — — (489) (13,606) (130,666) Transfer to Strategic Developments and Operating Assets Segments — — — (1,175) — (1,175) Other (24,076) (9,699) 114 58 (3,356) (36,959) Balance June 30, 2026 $ 496,578 $ 1,297,342 $ 548,664 $ 185,659 $ 118,531 $ 2,646,774 (a)Development expenditures are inclusive of capitalized interest and property taxes. (b)MUD reimbursable costs represent land development expenditures transferred to MUD Receivables. Strategic Developments Our Strategic Developments assets generally require substantial future development to maximize their value. Other than our condominium properties, most of the properties and projects in this segment do not generate revenues. Our expenses relating to these assets are primarily related to costs associated with constructing the assets, selling condominiums, carrying costs including, but not limited to, property taxes and insurance, and other ongoing costs relating to maintaining the assets in their current condition. If we decide to redevelop or develop a Strategic Developments asset, we expect that with the exception of the residential portion of our condominium projects, upon completion of development, the asset would likely be reclassified to Operating Assets when the asset is placed in service and NOI would become a meaningful measure of its operating performance. All development costs discussed herein are exclusive of land costs. Segment EBT Segment EBT for Strategic Developments is presented below: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change Condominium rights and unit sales $ 706,311 $ 193 $ 706,118 NM $ 709,445 $ 535 $ 708,910 NM Rental revenue (2) (26) 24 92 % (2) 33 (35) (106) % Other revenues 1,123 547 576 105 % 2,396 1,000 1,396 140 % Total revenues 707,432 714 706,718 NM 711,839 1,568 710,271 NM Condominium rights and unit cost of sales (575,389) (811) (574,578) NM (578,523) (1,053) (577,470) NM Operating costs (7,092) (3,760) (3,332) (89) % (11,526) (7,336) (4,190) (57) % Rental property real estate taxes (505) (615) 110 18 % (1,026) (1,163) 137 12 % Total operating expenses (582,986) (5,186) (577,800) NM (591,075) (9,552) (581,523) NM Segment operating income (loss) 124,446 (4,472) 128,918 NM 120,764 (7,984) 128,748 NM Depreciation and amortization (2,068) (1,076) (992) (92) % (4,125) (2,234) (1,891) (85) % Interest income (expense), net 4,097 4,633 (536) (12) % 9,071 9,279 (208) (2) % Other income (loss), net — 132 (132) (100) % (889) (1,130) 241 21 % Equity in earnings (losses) from unconsolidated ventures 76 87 (11) (13) % (4,906) 174 (5,080) NM Gain (loss) on sale or disposal of real estate and other assets, net — 1,657 (1,657) (100) % — 1,657 (1,657) (100) % Segment EBT $ 126,551 $ 961 $ 125,590 NM $ 119,915 $ (238) $ 120,153 NM NM Not meaningful. HHH 2026 FORM 10-Q | 57 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents For the three months ended June 30, 2026: Strategic Developments segment EBT increased $125.6 million compared to the prior-year period primarily due to the following: –Condominium sales, net of cost of sales increased $131.5 million due to the closing of 527 units at The Park Ward Village in the current period. For the six months ended June 30, 2026: Strategic Developments segment EBT increased $120.2 million compared to the prior-year period primarily due to the following: –Condominium sales, net of cost of sales increased $131.4 million due to the closing of 527 units at The Park Ward Village and the remaining 6 units at Ulana Ward Village in the current period. –Equity earnings decreased $5.1 million due to the recognition of the Company’s share of a loss on sale of land at our West End Alexandria joint venture. See Note 5 - Investments in Unconsolidated Ventures in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. Condominiums Condominium revenue is recognized when construction of the condominium tower is complete and unit sales close, leading to variability in revenue recognized between periods. Completed Condominiums Ulana Ward Village was completed in the fourth quarter of 2025, and the remaining six units closed in the first quarter of 2026. The Park Ward Village was completed in the second quarter of 2026, and 527 of the 545 units were closed in the second quarter of 2026. As of June 30, 2026, The Park Ward Village is 97% sold with the remaining units in condominium inventory. Under Construction and Predevelopment Condominiums The Company commenced construction on The Launiu in the first quarter of 2026. The following provides further detail for our under construction and predevelopment condominium projects as of June 30, 2026: Location Units Under Contract Total Units Total % of Units Under Contract Completion Date Under construction Kalae Honolulu, HI 309 329 94 % 2028 The Ritz-Carlton Residences The Woodlands, TX 85 111 77 % 2027 The Launiu Honolulu, HI 362 485 75 % 2028 Predevelopment Melia Honolulu, HI 154 220 70 % 2030 ‘Ilima Honolulu, HI 93 148 63 % 2030 HHH 2026 FORM 10-Q | 58 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents Corporate Income, Expenses, and Other Items The following table contains certain corporate-related and other items not related to segment activities and that are not otherwise included within the segment analyses. Variances related to income and expenses included in NOI or EBT are explained within the previous segment discussions. Significant variances for consolidated items not included in NOI or EBT are described below: Three Months Ended June 30, Six Months Ended June 30, thousands except percentages 2026 2025 $ Change % Change 2026 2025 $ Change % Change General and administrative expenses $ (36,136) $ (34,552) $ (1,584) (5) % $ (61,894) $ (56,988) $ (4,906) (9) % Gain (loss) on sale of MUD receivables (555) (48,197) 47,642 99 % (555) (48,197) 47,642 99 % Corporate interest expense, net (22,245) (21,930) (315) (1) % (42,551) (44,120) 1,569 4 % Gain (loss) on extinguishment of debt — — — NM (10,226) — (10,226) NM Corporate depreciation and amortization (1,135) (856) (279) (33) % (2,075) (1,603) (472) (29) % Vantage income (loss) before income taxes (20,765) — (20,765) NM (20,765) — (20,765) NM Income tax (expense) benefit (49,957) 3,821 (53,778) NM (52,575) 385 (52,960) NM Other (4,677) (4,237) (440) (10) % (9,592) (8,925) (667) (7) % Total Corporate income, expenses, and other items $ (135,470) $ (105,951) $ (29,519) (28) % $ (200,233) $ (159,448) $ (40,785) (26) % NM Not meaningful. For the three months ended June 30, 2026: Corporate income, expenses, and other items were unfavorably impacted compared to the prior-year period by the following: –Income tax expense increased $53.8 million primarily due to an increase in Income before income taxes. Refer to Note 13 - Income Taxes in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. –Vantage loss before income taxes of $20.8 million is included in the Company’s results following the completion of the Vantage Acquisition. Refer to the Vantage Post-Acquisition Results section below for further discussion of this activity. –General and administrative expenses increased $1.6 million primarily due to $15.4 million of Vantage Acquisition transaction costs. This increase was partially offset by a decrease of $12.6 million in compensation and benefits, primarily due to the strategic reduction in force in 2025. Corporate income, expenses, and other items were favorably impacted compared to the prior-year period by the following: –Loss on sale of MUD receivables decreased $47.6 million as a result of a $0.6 million loss recognized in the second quarter of 2026, compared to a $48.2 million loss recognized in the second quarter of 2025. Refer to Note 1 - Presentation of Financial Statements and Significant Accounting Policies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. For the six months ended June 30, 2026: Corporate income, expenses, and other items were unfavorably impacted compared to the prior-year period by the following: –Income tax expense increased $53.0 million primarily due to an increase in Income before income taxes. –Vantage loss before income taxes of $20.8 million is included in the Company’s results following the completion of the Vantage Acquisition. –Loss on extinguishment of debt increased $10.2 million due to payment of the bond call premium and accelerated amortization of related debt issuance costs following the repayment of the $750.0 million 5.375% senior unsecured notes in the first quarter of 2026. Refer to Note 6 - Mortgages, Notes, and Loans Payable, Net in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. HHH 2026 FORM 10-Q | 59 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents –General and administrative expenses increased $4.9 million primarily due to $19.0 million of Vantage Acquisition transaction costs and an increase of $4.7 million in Pershing Square advisory fees in the current period. These increases were partially offset by a decrease of $16.3 million in compensation and benefits, primarily due to the strategic reduction in force in 2025. Corporate income, expenses, and other items were favorably impacted compared to the prior-year period by the following: –Loss on sale of MUD receivables decreased $47.6 million as a result of a $0.6 million loss recognized in the second quarter of 2026, compared to a $48.2 million loss recognized in the second quarter of 2025. Pershing Square Advisory Fees Pershing Square supports the Company’s diversified holding company strategy by providing certain investment and advisory services. Starting in the second quarter of 2025, the Company began paying Pershing Square a quarterly advisory fee that includes base and variable components. The variable fee is calculated based on the excess of the quarter-end stock price over a reference price. As such, no variable fee is owed in a period that the quarter-end stock price does not exceed the reference price. Refer to Note 3 - Pershing Square in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information on the advisory fee. The base and variable components of the quarterly advisory fee are detailed below: Three Months Ended June 30, Six Months Ended June 30, thousands 2026 2025 $ Change % Change 2026 2025 $ Change % Change Base fee $ 3,786 $ 2,349 $ 1,437 61 % $ 7,572 $ 2,349 $ 5,223 NM Variable fee 64 540 (476) (88) % 64 540 (476) (88) % Total Pershing Square advisory fee $ 3,850 $ 2,889 $ 961 33 % $ 7,636 $ 2,889 $ 4,747 164 % NM Not meaningful. Vantage Post-Acquisition Results The discussion below summarizes the contribution of Vantage to our consolidated results for the three and six months ended June 30, 2026. The amounts reflect only the period from the acquisition date through June 30, 2026. As the acquisition was completed during the current period, there is no corresponding prior-year period for these operations, and as such period-over-period analysis for Vantage is not applicable. Due to the limited post-acquisition period, the results discussed below are not necessarily indicative of expected performance over the full year. See Note 2 - Vantage Acquisition in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information about the Vantage Acquisition. Vantage operates in the United States (U.S.) and Bermuda and writes business on both an admitted and excess and surplus basis. Product lines offered by its U.S. insurance subsidiaries include casualty, property, professional liability, financial lines, healthcare, construction, and political risk and credit. Products offered by its Bermuda subsidiary include financial and professional lines and healthcare and excess casualty. Vantage’s reinsurance operations consist of products offered by its Bermuda subsidiary and product lines offered include specialty, property and casualty, financial lines, and property catastrophe. Vantage also earns net investment income and net fee income. Key drivers of the operating results of Vantage include: –The level and mix of gross and net written and earned premiums by line of business and geography; –The frequency and severity of insured loss activity, including catastrophe events and prior‑year reserve development; –The structure, cost, and recoveries associated with our reinsurance programs; –Investment income earned from the insurance investment portfolio and required regulatory capital; and –Investment gains and losses attributable to the Company’s insurance investment portfolio. We expect to refine our disclosure of applicable key performance indicators for Vantage as we complete integration activities and as the CODM incorporates these metrics into ongoing operating decisions. HHH 2026 FORM 10-Q | 60 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents The following table presents the post-acquisition activity associated with Vantage included in the three and six months ended June 30, 2026: thousands Three and Six Months Ended June 30, 2026 Gross written insurance premiums $ 156,059 Net written insurance premiums $ 107,208 Net earned insurance premiums $ 97,247 Insurance claims and claim expenses (55,210) Insurance underwriting expenses Acquisition costs (1,129) VOBA amortization (20,239) Other insurance underwriting expenses (16,013) Underwriting income (loss) 4,656 Net insurance investment income 10,988 Other revenues 4,906 Depreciation and amortization (1,268) Other expenses (1,679) Investment gain (loss), net (38,278) Other income (loss), net (90) Vantage income (loss) before income taxes $ (20,765) Ratios (a) Loss ratio 56.8 % Expense ratio 38.4 % Combined ratio 95.2 % (a)Given the short measurement period and normal volatility in property and casualty results, we do not consider the post-acquisition ratios to be representative of expected full-year performance. Net insurance earned premiums include insurance and reinsurance premiums. Insurance claims and claim expenses include incurred losses on insured events and changes in estimates of unpaid claims and claim expenses, including both case reserves and incurred but not reported reserves. This corresponds to a loss ratio (Insurance claims and claim expenses to Net insurance earned premiums) of 56.8% in the post-acquisition period. Refer to Note 9 - Reserves for Claims and Claim Expenses in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. Insurance underwriting expenses include $20.2 million of VOBA amortization, $16.0 million of other insurance underwriting expenses comprised of costs directly attributable to operating the insurance business, including certain personnel, technology and administrative functions that support underwriting activities, and $1.1 million of amortization of deferred acquisition costs incurred subsequent to the Vantage Acquisition. This corresponds to an expense ratio (Insurance underwriting expenses to Net insurance earned premiums) of 38.4% in the post-acquisition period. Net insurance investment income includes interest and dividend income related to the Company’s investments in fixed maturity securities, equity securities, and short-term investments, less related expenses. See Note 4 - Investments in Fixed Maturity and Equity Securities in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information about the Company’s investments. Other revenues and other expenses include fee income and related expenses associated with AdVantage. See Note 1 - Presentation of Financial Statements and Significant Accounting Policies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. Investment gain (loss), net includes $36.0 million of unrealized losses related to equity securities, $2.1 million of net realized losses related to the sale of fixed maturity securities, and $0.2 million related to the recognition of losses on fixed maturity securities in an unrealized loss position that the Company intends to sell before recovery of the amortized cost basis. HHH 2026 FORM 10-Q | 61 MANAGEMENT’S DISCUSSION AND ANALYSISRESULTS OF OPERATIONS Table of Contents LIQUIDITY AND CAPITAL RESOURCES We continue to maintain a strong balance sheet and endeavor to ensure that we maintain the financial flexibility and liquidity necessary to fund future growth. As of June 30, 2026, we had $2.6 billion of cash and cash equivalents, including cash held at Vantage, $515.0 million of undrawn capacity on our Secured Bridgeland Notes, and $970.3 million of undrawn lender commitments available to be drawn for property development, subject to certain restrictions. Cash Flows Six Months Ended June 30, thousands 2026 2025 Cash provided by (used in) operating activities $ 277,131 $ (47,651) Cash provided by (used in) investing activities (357,454) (122,671) Cash provided by (used in) financing activities 1,348,519 970,648 Operating Activities Each segment’s relative contribution to our cash flows from operating activities will likely vary significantly from period to period given the changing nature of our development focus and the timing of condominium and land sale closings. Our operating cash flows consist of the following (1) condominium deposits received from contracted units and proceeds from condominium closings offset by other various cash uses related to condominium development and sales activities, (2) revenues from MPC land sales offset by development costs associated with the land sales business and acquisitions of land that is intended to ultimately be developed and sold, (3) recurring contractual revenues from operating leases, and (4) post-acquisition operating cash flows attributable to Vantage, primarily related to insurance and reinsurance premiums collected, reinsurance recoverables, fee income, and investment income, offset by claim payments, ceded and retro reinsurance payments, and underwriting costs. Net cash provided by operating activities was $277.1 million in the six months ended June 30, 2026, and net cash used in operating activities was $47.7 million in the six months ended June 30, 2025. The change in operating activities of $324.8 million was primarily due to an increase in cash provided by condominium towers, primarily due to the closings at The Park Ward Village in the current period, an increase in the cash provided by Vantage in the post-acquisition period, and an increase in MPC land sales, partially offset by a decrease in cash provided related to higher proceeds from the sale of MUD receivables in the prior period and an increase in MPC development expenditures. Investing Activities Net cash used in investing activities was $357.5 million in the six months ended June 30, 2026, and $122.7 million in the six months ended June 30, 2025. The $234.8 million increase in net cash used in investing activities was primarily due to $1.6 billion of cash used for the Vantage Acquisition, net of cash acquired, and $1.1 billion of cash used to purchase equity securities in the current period. These increases were partially offset by $2.3 billion of cash received for the sale of fixed maturity securities in the current period, and an increase in cash received of $119.3 million for the sale of properties, primarily due to the sale of two multifamily properties in The Woodlands in the current period, compared to the sale of two land parcels and a retail space in Ward Village in the prior period. Financing Activities Net cash provided by financing activities was $1.3 billion in the six months ended June 30, 2026, and $970.6 million in the six months ended June 30, 2025. The $377.9 million increase in cash provided by financing activities was primarily due to $1.2 billion increase in proceeds from mortgages, notes, and loans payable, primarily related to the issuance of $1.0 billion of new unsecured notes and a $300.0 million mortgage secured by Downtown Summerlin in the current period, as well as $997.4 million of net proceeds from the issuance of Series A Preferred Stock in the current period. These increases were partially offset by a decrease in cash provided of $862.9 million related to net proceeds received in the prior period for the common stock issuance to Pershing Square, a $906.8 million increase in cash used related to principal payments on mortgages, notes, and loans payable, primarily related to the repayment of $750 million of existing unsecured notes in the current period, as well as an $18.6 million increase in deferred financing costs and bond issuance costs related to these transactions. HHH 2026 FORM 10-Q | 62 Table of Contents Short- and Long-Term Liquidity Short-Term Liquidity In the next 12 months, we expect to continue to drive meaningful value creation following our transition to a diversified holding company. From our real estate operations, we expect our primary sources of cash to include cash flow from MPC land sales and condominium closings, cash generated from our operating assets, first mortgage financings secured by our assets, and deposits from condominium sales (which are restricted to funding construction of the related developments). We expect our primary uses of cash to include condominium pre-development and development costs, debt principal payments and debt service costs, MPC land development costs, other strategic developments costs, and general operating costs. From our insurance operations, we expect our primary sources of cash to include premiums collected from policyholders, investment income earned from our investment portfolio, recoveries from reinsurers, proceeds from the sale or maturity of investments, and if needed, available borrowings under Vantage’s Revolving Credit Facility. We expect our primary uses of cash to include payment of claims, premiums ceded to reinsurers, commissions and other policy acquisition costs, and general operating expenses. Cash flows from operations may be impacted by the timing of premium collections, claim payments, and changes in reinsurance balances. Actual claim payment patterns may differ from current estimates due to a variety of factors, including the size and timing of individual losses, changes in the legal and regulatory environment, and broader economic conditions. The Company currently intends to reposition Vantage’s investment portfolio to include cash, short-term U.S. Treasury securities, and publicly traded equity securities. In June 2026, the Company began implementing this strategy by divesting a significant portion of its available-for-sale fixed maturity securities and initiating investments in equity securities. The Company expects to divest the majority of its remaining available-for-sale fixed maturity securities prior to the end of 2026. We believe that our sources of cash, including existing cash on hand, will provide sufficient liquidity to meet our existing obligations and anticipated ordinary course operating expenses for at least the next 12 months. Long-Term Liquidity We expect our long-term sources and uses of cash for our real estate and insurance operations to continue to align with those mentioned above. For our real estate operations, we expect long-term operating cash flows to increase over time as a result of increased MPC land sales driven by price appreciation, rental revenue growth and continued condominium sales. These cash flows are expected to be reinvested into the real estate business to fund development opportunities, which are capital intensive and will likely require significant additional funding, if and when pursued. We currently expect that any additional funding beyond those sources listed above would be raised with a mix of construction, bridge, and long-term financings, or by entering into joint venture arrangements. We cannot provide assurance that financing arrangements for our properties will be on favorable terms to us or occur at all, which could have a negative impact on our liquidity and capital resources. In addition, we typically must provide completion guarantees to lenders in connection with their financing for our projects. For our insurance operations, we expect cash inflows to grow over time through the optimization of underwriting profitability and investment strategies. Insurance operations generally provide liquidity as premiums are received in advance of the payment of related claims, although the period between the occurrence of a claim and settlement of the associated liability may extend for many years. The Company’s investment strategy is managed to establish a level of cash, investments, and expected future cash flow that will be able to meet foreseeable payment obligations. The Company’s ability to deploy cash held at the insurance-subsidiary level for long-term uses is subject to various limitations and considerations, including the timing and uncertainty of claim payments, regulatory capital and solvency requirements applicable to its insurance subsidiaries, and restrictions on the ability of such subsidiaries to pay dividends or other distributions to the parent company. While management believes that existing cash flows, invested assets, and other available sources of liquidity will be sufficient to satisfy long-term obligations, the ultimate amount and timing of claim payments may differ materially from current estimates. In addition, the Company must maintain sufficient liquidity to support its insurance liabilities and meet policyholder obligations under a range of stress scenarios. As a result, a significant portion of insurance-related cash and invested assets may not be readily available for discretionary uses. The Series A Preferred Stock issued by HHH to Pershing Square is convertible into equity interests of Vantage if not redeemed by the end of the seventh fiscal year post-transaction. HHH has the right, but not the obligation, to redeem the Series A Preferred Stock over the next seven years. Refer to Note 3 - Pershing Square in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. HHH 2026 FORM 10-Q | 63 Table of Contents To the extent real estate operations generate excess cash flows, we expect to use such excess cash flow to redeem the Series A Preferred Stock, invest additional primary capital into the insurance business and, over time, pursue the acquisition of other high-quality operating companies. The Vantage Acquisition is expected to have other long‑term implications for the Company’s liquidity profile, although the magnitude and timing of these impacts cannot yet be determined. The Company actively manages its liquidity position and capital resources to ensure that it can meet both its short-term and long-term obligations while maintaining financial flexibility. Contractual Cash Obligations and Commitments The following table aggregates our contractual cash obligations and commitments as of June 30, 2026: thousands Remaining in 2026 2027 2028 2029 2030 Thereafter Total Mortgages, notes, and loans payable $ 229,512 $ 596,007 $ 293,099 $ 1,048,015 $ 366,629 $ 2,967,139 $ 5,500,401 Interest payments (a) 151,985 270,915 237,601 191,764 163,720 268,505 1,284,490 Operating lease obligations 1,524 1,729 911 871 637 5,810 11,482 Total $ 383,021 $ 868,651 $ 531,611 $ 1,240,650 $ 530,986 $ 3,241,454 $ 6,796,373 (a)Interest is based on the borrowings that are presently outstanding and current floating interest rates. Debt As of June 30, 2026, the Company had $5.5 billion of outstanding debt, $970.3 million of undrawn lender commitment available to be drawn for property development, subject to certain restrictions, and $515.0 million of undrawn capacity on our Secured Bridgeland Notes. Vantage has a $75.0 million revolving credit facility with the option to increase the aggregate amount by $50.0 million at the lender’s discretion. This facility matures in January 2028. As of June 30, 2026, there were no outstanding borrowings under this facility. In February 2026, HHC, the Company’s wholly owned subsidiary, issued $500.0 million of 5.875% senior unsecured notes due 2032 and $500.0 million of 6.125% senior unsecured notes due 2034. These notes will pay interest semi-annually. HHC used the net proceeds to redeem its outstanding $750.0 million 5.375% senior unsecured notes due 2028, including the payment of premiums, accrued and unpaid interest and expenses related to such redemption, and will use the remaining proceeds for general corporate purposes. Refer to Note 6 - Mortgages, Notes, and Loans Payable, Net in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. The Company has a collateral maintenance obligation for Floreo, its unconsolidated venture. See Note 12 - Commitments and Contingencies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. Debt Compliance As of June 30, 2026, the Company was not in compliance with certain property-level debt covenants, which did not have a material impact on the Company’s liquidity or its ability to operate these assets. As a result, the excess net cash flow after debt service from the underlying properties became restricted. While the restricted cash can not be used for general corporate purposes, it can be used to fund operations of the underlying assets. Net Debt The following table summarizes our Net Debt on a segment basis as of June 30, 2026. The Company revised the definition of its non-GAAP measure, Net Debt, to simplify its calculation and recast the prior period to conform to the new presentation. Under the revised definition, Net Debt excludes the impact of unamortized deferred financing costs and our ownership share of debt of our unconsolidated ventures, whereas prior periods included these amounts. In addition, under the revised definition, Net Debt is reduced only by readily available cash sources, consisting of Cash and cash equivalents. Prior periods included our ownership share of our unconsolidated ventures’ cash and certain receivable balances as liquidity sources, which are excluded under the revised definition. HHH 2026 FORM 10-Q | 64 Table of Contents Net Debt is now defined as Mortgages, notes, and loans payable, excluding the impact of unamortized deferred financing costs, reduced by Cash and cash equivalents available to satisfy such obligations. Management believes the updated definition provides a more meaningful measure of the Company’s leverage by (i) focusing on obligations for which the Company has primary responsibility and control and (ii) using a more conservative measure of liquidity that reflects only readily available cash resources. This change enhances transparency and comparability for investors. Although Net Debt is a non-GAAP financial measure, we believe that such information is useful to our investors and other users of our financial statements as Net Debt and its components are important indicators of our overall liquidity, capital structure, and financial position. However, it should not be used as an alternative to our debt calculated in accordance with GAAP. thousands June 30, 2026 December 31, 2025 Operating Assets debt $ 2,686,141 $ 2,448,784 MPC debt 154,681 163,534 Strategic Developments debt 359,579 481,896 Senior unsecured notes 2,300,000 2,050,000 Unamortized deferred financing costs (43,998) (34,386) Mortgages, notes, and loans payable, net 5,456,403 5,109,828 Less: Unamortized deferred financing costs 43,998 34,386 Less: Cash and cash equivalents (a) (2,647,959) (1,468,507) Net Debt $ 2,852,442 $ 3,675,707 (a)Includes $1.9 billion of cash and cash equivalents held at Vantage at June 30, 2026. Insurance-Specific Considerations Insurance Investment Portfolio The following table provides detail of the Vantage investment portfolio at fair value as of June 30, 2026: June 30, 2026 thousands Fair Value % of Total Cash, cash equivalents, and restricted cash (a) $ 2,033,218 60 % Investments in fixed maturity securities, AFS (b) 246,583 7 % Investments in equity securities 1,077,535 32 % Short-term investments 27,822 1 % Total $ 3,385,158 100 % (a)Represents cash, cash equivalents, and restricted cash held at the Vantage level only. (b)The weighted-average credit rating of the Company’s AFS fixed maturity securities portfolio was AA+ as of June 30, 2026. Insurance Claims Following the Vantage Acquisition, the Company is obligated to pay claims arising from property and casualty contracts issued by our insurance subsidiaries. The timing and amount of the payments under insurance and reinsurance contracts are contingent upon the outcome of future events and actual payments will likely vary, perhaps materially, from any forecasted payments, as well as from the liabilities recorded in our Condensed Consolidated Balance Sheets. As of June 30, 2026, the reserve for claims and claim expenses was $2.1 billion, with $0.5 billion expected to be settled in less than one year and $1.6 billion expected to be settled in future years. The estimated timing of payments was determined using Vantage’s historical claims payment experience, supplemented by industry and peer group data. Given the inherent uncertainty in projecting the timing of claim settlements, actual cash outflows in any period may differ materially from the amounts presented. The reserve amounts disclosed above exclude the impact of anticipated amounts recoverable on unpaid losses from reinsurers of $563.9 million as of June 30, 2026. Refer to Note 9 - Reserves for Claims and Claim Expenses in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. We anticipate that these payments will be funded by operating cash flows. HHH 2026 FORM 10-Q | 65 Table of Contents Insurance-Related Statutory Capital and Dividend Restrictions The Company’s insurance subsidiaries are subject to insurance laws and regulations in the jurisdictions in which they operate and have regulatory capital and solvency requirements and restrictions on the ability of such subsidiaries to pay dividends to the parent company. The ability of the insurance and reinsurance subsidiaries to pay dividends to the parent company is also influenced by the maintenance of financial strength ratings assigned by independent rating agencies. Additionally, as a condition to the approval by the Delaware Department of Insurance (the Department) of the Vantage Acquisition, the Company has agreed that, until June 4, 2028, any dividends (whether ordinary or otherwise) by the Company’s Delaware insurance subsidiaries will require the Department’s prior approval. As of June 30, 2026, all insurance subsidiaries exceeded minimum regulatory capital requirements. The Company’s insurance subsidiaries are required to maintain assets on deposit, which primarily consist of restricted cash and fixed maturity securities, with various regulatory authorities to support their operations. As of June 30, 2026, the assets on deposit available to settle insurance and reinsurance liabilities to third parties were $307.6 million. CRITICAL ACCOUNTING POLICIES AND ESTIMATES The preparation of financial statements in accordance with GAAP requires management to make informed judgments, assumptions, and estimates that affect the reported amounts of assets, liabilities, revenues, and expenses. We base our estimates on historical experience and on various other assumptions that we believe to be reasonable under the circumstances. Changes in facts and circumstances or additional information may result in revised estimates, and actual results may differ from these estimates. Other than as set forth below, there are no material changes to the critical accounting policies and estimates previously disclosed in our 2025 Annual Report. Following the acquisition of Vantage, the Company recognized reserves for claims and claim expenses, goodwill, and other intangible assets. The preliminary purchase price allocation and the ongoing determination of the reserves for claims and claim expenses require complex or significant judgments and include estimates about matters which are inherently uncertain. These estimates are critical to the understanding of our financial condition and operating results, and as such, accounting for business combinations and reserves for claims and claim expenses represent new critical accounting estimates. A discussion of our significant accounting policies impacted by the Vantage Acquisition, including further discussion of the accounting policies described below, can be found in Note 1 - Presentation of Financial Statements and Significant Accounting Policies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report. Accounting for Business Combinations Methodology The Vantage Acquisition was accounted for as a business combination under ASC 805, which requires the assets acquired and liabilities assumed to be recorded at their estimated acquisition-date fair values. The preliminary purchase price allocation includes the recognition of identifiable intangible assets and any excess of the purchase price over the estimated fair value of net tangible and identifiable intangible assets acquired as goodwill, if applicable. The Company will finalize the purchase price allocation during the measurement period as additional information becomes available, including final appraisals of certain acquired assets and assumed liabilities and final underlying tax bases. The Company engaged independent valuation specialists to assist management in determining the fair values of certain acquired assets and assumed liabilities. The most significant areas of judgment in the preliminary fair value assessment relate to broker relationships, trade name, internally developed technology, value of business acquired (VOBA), insurance licenses, and reserves for claims and claim expenses, net of reinsurance recoverable on unpaid losses. The resulting fair values and useful lives assigned to acquisition-related intangible assets will affect the amount and timing of future amortization expense. HHH 2026 FORM 10-Q | 66 Table of Contents Judgments and Uncertainties Determining the fair value of the acquired assets and assumed liabilities required significant judgment and estimates and was based on information available as of the acquisition date. The valuation of broker relationships was based on the multi-period excess earnings method and incorporated significant assumptions including projected net premiums written, retention rates, normalized growth assumptions, contributory asset charges, discount rates, long-term tax rates, and investment yields. The trade name was valued using the relief-from-royalty method, which required assumptions regarding royalty rates, projected net premiums written, growth assumptions, and discount rates. Internally developed technology was valued using the replacement cost method and incorporated estimates of labor costs, development timing, developer’s profit, entrepreneurial incentive, and obsolescence. VOBA was valued using a discounted cash flow model applied to the run-off of unearned premium reserves, net of reinsurance, and incorporated assumptions for loss and expense ratios, payment patterns, capital requirements, risk margin, and discount rates. Reserves for claims and claim expenses, net of reinsurance recoverable on unpaid losses, were measured using a discounted cash flow model applied to the actuarial run-off of recorded reserves and incorporated assumptions related to the time value of money, risk margin, actuarial payment patterns, capital requirements, cost of capital, and reserve payout assumptions. Changes in these assumptions or the receipt of additional information during the measurement period could result in material revisions to the preliminary purchase price allocation, including the amounts assigned to identifiable intangible assets, insurance-related liabilities, and goodwill. Reserves for Claims and Claim Expenses Nature of the Estimate As a result of our June 4, 2026 acquisition of Vantage, reserves for claims and claim expenses have become a critical accounting estimate in our consolidated financial statements. These reserves represent management’s estimate of the unpaid portion of the ultimate liability for claims and claim adjustment expenses for insured and reinsured events that have occurred on or before the balance sheet date. They comprise (i) case reserves for claims that have been reported to us and (ii) reserves for losses incurred but not reported (IBNR), which also reflect expected development on reported claims. The reserves were initially recorded at fair value as of the acquisition date in accordance with the acquisition method of accounting and are subsequently estimated using the actuarial methods and assumptions described below. We consider this the most significant accounting judgment associated with the acquired insurance and reinsurance operations because the ultimate cost of claims is not known at the reporting date, the estimate requires significant judgment, and a change in the estimate could have a material effect on our financial condition and results of operations. Methodology In establishing these reserves, management considers claim-specific information, historical loss experience, actuarial analyses, and other relevant information, including expected loss ratios, reported and paid loss development patterns, claim frequency and severity trends, underwriting and pricing information, business mix, policy terms and conditions, cedent and broker information, industry data, and current economic, legal, regulatory, inflationary, and catastrophe-related conditions. The relative importance of these factors varies by line of business and by the maturity of the underlying loss experience. Where company-specific history is limited, management supplements internal data with industry data, which was a primary source of loss development patterns for many lines given the relatively short loss history of the acquired operations. Management employs multiple actuarial methods to estimate ultimate losses, including the paid and reported (incurred) loss development (chain ladder) methods, the paid and reported Bornhuetter-Ferguson methods, frequency and severity methods, and the expected loss ratio method. The relative weight assigned to each method is a matter of actuarial judgment that depends on the characteristics of each line of business, the maturity of the cohort year being estimated, and the availability of credible historical data. In addition to quantitative actuarial indications, reserve estimates incorporate qualitative adjustments for factors that may not be fully captured by historical experience, such as judicial and litigation trends, legislative and regulatory activity, underwriting and business-mix changes, and, for reinsurance business, changes in cedents’ reserving and reporting practices. Judgments and Uncertainties Estimating claims and claim expense reserves requires significant judgment because the ultimate cost of claims is not known at the reporting date and may vary materially from recorded amounts. The most significant judgments include the selection of expected loss ratios, loss development patterns, claim severity assumptions, and reporting patterns, particularly for lines of business with longer reporting or settlement patterns, reinsurance exposures, or limited company-specific historical experience. This uncertainty is affected by numerous factors, including claim emergence and reporting patterns, the length of time required to resolve claims, severity trends, catastrophe activity, inflation and social inflation, litigation trends, legislative and regulatory developments, and changes in business mix. Because these estimates are inherently uncertain, actual losses may differ materially from recorded reserves. HHH 2026 FORM 10-Q | 67 Table of Contents Because the acquisition closed on June 4, 2026, our results for the quarter ended June 30, 2026, include only approximately one month of post-acquisition activity for Vantage. Accordingly, while the reserve balance at June 30, 2026, reflects management’s best estimate based on information available at that date, early post-acquisition claims activity may be less predictive of future development, and reserve estimates may be adjusted in future periods as additional post-acquisition experience becomes available. At June 30, 2026, our reserves for claims and claim expenses related to Vantage were approximately $2.1 billion on a gross basis and $1.6 billion net of reinsurance recoverable on unpaid losses. The gross reserves represented approximately 19% of our total consolidated liabilities and 53% of our total consolidated stockholders’ equity at that date. For the period from June 4, 2026 through June 30, 2026, changes in estimates of prior-period claims and claim expense reserves were not material. Given the interrelationship of assumptions across lines of business, the limited period of post-acquisition activity, and the judgment involved in estimating reserves, management has not identified a single-assumption sensitivity that would be representative of the potential variability in the loss reserve estimate as of June 30, 2026. If a quantitative sensitivity to a reasonably likely change in a significant assumption becomes material and reasonably available, we will disclose the estimated effect of that change. While we believe that recorded loss reserves at June 30, 2026, are adequate, new information, events, or circumstances may result in ultimate losses that are materially greater or less than our recorded reserves, particularly with respect to catastrophe or large-event losses and longer-tail lines of business. For additional information, refer to Note 9 - Reserves for Claims and Claim Expenses in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report. HHH 2026 FORM 10-Q | 68 MARKET RISK AND CONTROLS AND PROCEDURES Table of Contents

Interest Rate Risk We are subject to interest rate risk with respect to our variable-rate financings in that increases in interest rates would cause our payments under such financings to increase. With respect to fixed-rate financings, increases in interest rates could make it more difficult to refinance such debt when it becomes due. As properties are placed into service and become stabilized, we typically refinance the variable-rate debt with long-term fixed-rate debt. The Company uses derivative instruments to manage its interest rate risk, primarily through the use of interest rate swaps, caps, and collars. The Company had $1.4 billion of variable-rate debt outstanding at June 30, 2026, of which $656.5 million was swapped to a fixed rate through the use of interest rate swaps and $641.9 million had interest rate cap contracts in place. Additionally, the interest rate caps and collars are on construction loans and mortgages with undrawn loan commitments of $136.2 million as of June 30, 2026, which will be covered by the interest rate cap and collar contracts upon drawing. Refer to Note 7 - Derivative Instruments and Hedging Activities in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. As of June 30, 2026, annual interest costs would increase approximately $1.0 million for every 1% increase in floating interest rates. The Company is focused on prudently limiting exposure to potentially higher interest rates based upon market dynamics and general expected financing activity. Generally, a significant portion of our interest expense is capitalized due to the level of assets we currently have under development; therefore, the impact of a change in our interest rate on our Condensed Consolidated Statements of Operations would be less than the total change in interest costs, but we would incur higher cash payments and the development costs of our assets would be higher, resulting in greater depreciation or cost of sales in later years. Equity Price Risk Investments in equity securities represent the most significant portion of our consolidated investment portfolio. The Company seeks to invest in businesses that possess excellent economics and management, and prefers to invest a meaningful amount in each company. Currently, our investments are concentrated in relatively few issuers. At June 30, 2026, approximately 78% of the aggregate fair value of our investments in equity securities was concentrated in seven companies. The Company expects to hold its investments for long periods and short-term price volatility is expected to occur in the future. We also maintain significant levels of shareholder capital and ample liquidity to provide a margin of safety against short-term price volatility. The following table summarizes our investments in equity securities and the estimated effects of a hypothetical 10% increase or decrease in market prices as of June 30, 2026. Fair Value Hypothetical Price Change Est. Fair Value after Hypothetical Change in Price Est. Increase (Decrease) in Pre-Tax Net Income Investments in equity securities $ 1,077,535 10% increase $ 1,185,289 $ 107,754 10% decrease 969,782 (107,754) Credit Risk Following the Vantage acquisition, the Company is exposed to credit risk with respect to its third-party reinsurers. Although reinsurers are contractually obligated to reimburse the Company for covered claims, the Company remains primarily liable to its policyholders for all amounts ceded under its reinsurance agreements. Accordingly, reinsurance does not discharge the Company’s ultimate obligation to pay claims and amounts recoverable from reinsurers may not be fully collectible. The Company manages this exposure by placing reinsurance with counterparties that meet minimum financial strength requirements, including an A.M. Best rating of “A-” (Excellent) or higher at the time of placement, and by performing ongoing credit monitoring. In the event of a reinsurer downgrade or deterioration in credit quality, the Company may seek to mitigate exposure through actions such as commutation, novation, or the securing of collateral, including letters of credit. HHH 2026 FORM 10-Q | 69 Table of Contents

Please refer to Note 12 - Commitments and Contingencies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report.

There have been no material changes to the risk factors previously disclosed in our 2025 Annual Report, except as set forth below. On June 4, 2026, we completed our previously announced acquisition of Vantage (the Vantage Acquisition), and Vantage and its subsidiaries are now consolidated subsidiaries of the Company. As a result of the Vantage Acquisition, we are now subject to risks relating to the specialty insurance and reinsurance business conducted through Vantage. The risk factors set forth below under the caption “Financial Risks” amend and restate in their entirety the corresponding risk factors in the 2025 Annual Report; the remaining risk factors set forth below are new. The following risk factors should be read in conjunction with the risk factors disclosed in the 2025 Annual Report. RISKS RELATED TO THE VANTAGE ACQUISITION The Vantage Acquisition involves substantial integration risks, including diversion of management attention, potential disruption of our existing operations, challenges integrating systems and internal controls, and loss of certain Vantage personnel, any of which could prevent us from realizing the anticipated benefits of the transaction and materially adversely affect our business. The successful integration of Vantage's specialty insurance and reinsurance business into our operations is critical to realizing the anticipated strategic and financial benefits of the Vantage Acquisition, and there can be no assurance that the integration will be completed on the timeline we expect or that those benefits will be realized fully, in part, or at all. The Vantage Acquisition and related integration activities will continue to require substantial time and attention from our senior management and other key personnel, potentially diverting resources from our day-to-day operations, existing strategic priorities, and other business opportunities. We have limited prior experience operating in the specialty insurance and reinsurance industry, and we cannot assure you that our operational, financial, or administrative infrastructure will be adequate to manage the expanded operations of the combined company. Integrating the information technology systems, financial reporting and accounting processes, internal controls over financial reporting, actuarial systems, tax reporting and compliance systems, and other compliance programs of two distinct businesses is inherently complex and time-consuming. Although Vantage's subsidiaries, including its Bermuda subsidiary, are expected to be treated as U.S. taxpayers, integrating their tax reporting functions into our consolidated U.S. tax profile and coordinating that status with Vantage's continued obligations under Bermuda insurance regulation, may involve transitional complexity and cost. Any disruption, deficiency, or material weakness arising from the integration of Vantage's systems and internal controls could impair our ability to report our financial results accurately or on a timely basis, expose us to regulatory scrutiny or civil liability, and adversely affect the market price of our securities. Our ability to realize the benefits of the acquisition also depends on retaining certain key underwriting, actuarial, and claims personnel, whose specialized expertise and client relationships are impactful to the ongoing performance of Vantage's business. In addition, since the announcement of the Vantage Acquisition, Vantage has experienced changes in several senior leadership positions. Although we believe Vantage’s new leadership brings substantial relevant experience and strong counterparty relationships, the loss of such personnel and the potential for continued uncertainty associated with the acquisition could negatively impact the business. RISKS RELATED TO OUR INSURANCE OPERATIONS The Company conducts specialty insurance and reinsurance operations through Vantage and its subsidiaries. The following risks relate principally to those operations and are in addition to the other risks described in the 2025 Annual Report. HHH 2026 FORM 10-Q | 71 Table of Contents Vantage has a limited operating history, and its prior results may not be indicative of future performance. Vantage was founded in late 2020 and accordingly has a relatively short operating history. Its loss-development patterns, pricing assumptions, reserve estimates, and underwriting models are based on a thin historical data set as compared to longer-tenured insurance carriers, and the results Vantage has achieved in recent years may not be representative of future results. Vantage has also experienced rapid premium growth and continues to expand into new product lines and distribution channels. Entry into new lines of business or products entails risks that may not be apparent at the outset, including the investment of significant time and capital, the possibility that the marketplace does not accept new offerings, increased liability exposure, and the risk that our personnel, systems, and controls may not scale effectively. If Vantage is unable to manage these growth-related risks, or if its limited operating history proves to be a poor predictor of future loss experience, our business, financial condition, results of operations, and cash flows could be materially and adversely affected. Vantage’s insurance results depend on the accuracy of its underwriting, and inaccurate risk assessment could materially harm the Company’s business. Vantage’s profitability depends on its ability, and the ability of the managing general agents and other producers with which it transacts, to accurately assess the risks associated with the insurance and reinsurance business it writes and retains. This requires reliance on the judgment and experience of underwriting personnel, on actuarial and catastrophe-exposure models, and on data supplied by insureds, brokers, and third-party vendors. If Vantage misjudges the nature or extent of the risks it assumes, or if its models fail to capture all material exposures (including unmodeled accumulations and emerging coverage issues), it may fail to charge risk-adequate premium, may experience actual losses that materially exceed its probable maximum loss estimates, and may suffer adverse reserve development. Any of these outcomes could materially and adversely affect our business, financial condition, results of operations, and cash flows. Vantage’s reserve for claims and claim expenses may prove inadequate. Vantage establishes reserves for the estimated ultimate cost of all reported and unreported claims, including the related cost of adjusting those claims. These reserves do not represent an exact calculation of liability; they represent management’s estimate, based on actuarial analysis, of what Vantage expects ultimate settlement and administration of claims will cost. Because Vantage has a limited operating history, the historical data on which these estimates are based is limited. Emerging claim and coverage issues, changes in judicial interpretation of policy terms, changes in legislation or regulation, social-inflation trends, changes in claim-handling procedures, inflation in repair and replacement costs, and many other factors could cause actual ultimate losses to differ materially—and adversely—from current estimates. Any material increase in Vantage’s reserves would reduce earnings in the period the increase is recorded, erode statutory capital and surplus at Vantage’s insurance subsidiaries, and have a material adverse effect on our business, financial condition, results of operations, and cash flows. Vantage depends on third-party reinsurance, and Vantage may be unable to obtain it on acceptable terms or to collect amounts due from reinsurers. Vantage cedes a portion of the risks it underwrites to third-party reinsurers in order to manage its exposure to large losses and accumulations. The availability, scope, and cost of reinsurance depend on market conditions that are largely outside our control, and may change materially following catastrophe losses, changes in reinsurer appetite, or broader capacity contractions. If Vantage is unable to renew expiring reinsurance contracts on acceptable terms, to enter into new reinsurance arrangements, or to expand coverage as its book grows, its net loss exposure could increase. Vantage may then choose to reduce its underwriting commitments, retain greater net risk, or accept reinsurance terms that contain coverage exclusions or other limitations that leave gaps in protection that may expose Vantage to greater risk and greater potential losses. In addition, purchasing reinsurance does not relieve Vantage of its underlying obligations to its policyholders or ceding companies, so any inability to collect amounts due from reinsurers could adversely affect our financial condition and results of operations. Vantage therefore remains exposed to the credit and performance risk of its reinsurers. A reinsurer may withhold payment due to disputes over coverage, refuse to pay due to insolvency or financial distress, or otherwise fail to perform. Although Vantage regularly monitors the financial condition of its reinsurers, a significant reinsurer failure or a broader deterioration in the reinsurance market could materially and adversely affect our business, financial condition, results of operations, and cash flows. HHH 2026 FORM 10-Q | 72 Table of Contents Vantage’s business depends on its relationships with independent agents, brokers, wholesalers, and program administrators. Substantially all of Vantage’s products are distributed through independent retail agents, brokers, wholesalers, and program administrators. These intermediaries generally own the policyholder relationship and the related “renewal rights,” meaning that Vantage’s ability to retain and grow its book depends on its continued ability to attract and maintain favorable relationships with them. Further, Vantage is also dependent on the relationships its program administrators maintain with the agents and brokers from whom they source their business. These relationships may be terminated at any time, and there can be no assurance that compensation, service, product offerings, or financial-strength ratings will remain competitive. Any deterioration in Vantage’s distribution relationships, the loss of one or more material intermediaries, or the failure of a program administrator or managing general agent to operate within the underwriting authority granted to it could materially and adversely affect our business, financial condition, results of operations, and cash flows. In addition, Vantage could be adversely affected if the distributors with whom it does business exceed their granted authority, fail to transfer collected premium to Vantage or breach their obligations to Vantage and expose Vantage to liability. Vantage and its insurance subsidiaries are subject to extensive regulation, including risk-based capital and statutory accounting requirements. Vantage’s insurance and reinsurance subsidiaries are subject to extensive regulation by regulators in each of the jurisdictions in which they are domiciled or transact business, including U.S. state insurance departments, the Bermuda Monetary Authority, and other non-U.S. regulators. These regulations govern, among other things, licensing of insurers, agents, brokers, third-party administrators, managing general agents, reinsurance intermediaries, adjusters and other producers; capital, surplus, and risk-based-capital requirements; investment and underwriting limitations; affiliate transactions; the payment of dividends or other distributions from regulated subsidiaries to their parents; enterprise risk management; market conduct; financial reporting by Vantage’s U.S. insurance subsidiaries on a statutory-accounting-principles (SAP) basis; and changes in control. Insurance regulators have broad discretion to suspend, deny, or revoke licenses, require additional capital, impose corrective actions or fines, temporarily suspend a company from carrying on some or all of its activities or impose other penalties, and to subject insurers to supervision, rehabilitation, or liquidation. In some instances, where there is uncertainty as to applicability of regulations, Vantage follows practices based on its interpretations of regulations or practices that it believes to be generally followed by the industry, which may turn out to be different from the interpretations of regulatory authorities. The laws and regulations applicable to Vantage’s insurance operations, and the manner in which regulators interpret and enforce them, are subject to change. SAP and components of SAP are continuously reviewed by the National Association of Insurance Commissioners (the NAIC) and state insurance departments, and the NAIC has proposed and may continue to propose changes that, if adopted, could have negative effects on insurance industry participants. These changes, or changes proposed by other regulators, could include changes to investment and reserve valuation requirements, surplus requirements, dividend limitations, and risk-based-capital frameworks. Compliance with these requirements may limit Vantage’s flexibility to operate and grow its business, may restrict the ability of Vantage’s insurance subsidiaries to distribute cash to the Company, and may increase the cost of doing business. Failure to comply with applicable laws and regulations, or failure to maintain required capital and surplus, could subject Vantage’s subsidiaries to penalties or to the loss of authority to write new and renewal business, any of which could materially and adversely affect our business, financial condition, results of operations, and cash flows. Court or regulatory decisions affecting policy coverage, exclusions, or limitations, and insurance-related litigation, could increase our losses. The terms of insurance and reinsurance policies, including coverage grants, exclusions, and loss limitations, are subject to interpretation by courts and regulators. From time to time, courts have nullified, narrowed, or refused to enforce policy exclusions or limitations, and legislatures have enacted laws that retroactively modify policy terms or bar reliance on particular exclusions. Vantage’s policy wordings are intended to define and limit covered risks; however, an adverse judicial or legislative outcome could expose Vantage to claims and indemnity payments materially in excess of those it priced into the relevant policies. As is typical in the insurance industry, Vantage is also exposed to litigation arising from claim disputes under its policies and to other general commercial and corporate litigation. So-called “social inflation”—the trend toward larger jury verdicts, broader theories of liability, and litigation funding—can drive claim severity above historical patterns, particularly in casualty lines, leading to the potential for significant judgments. The outcome of any individual matter is inherently unpredictable, and adverse outcomes or trends could materially and adversely affect our business, financial condition, results of operations, and cash flows. HHH 2026 FORM 10-Q | 73 Table of Contents Competition in the insurance and reinsurance industry is intense. Vantage operates in a highly competitive specialty insurance and reinsurance environment that includes both domestic and international carriers, many of which have greater financial, operational, distribution, and brand resources than Vantage. Competition affects Vantage’s ability to price its products at risk-adequate rates, retain existing accounts, underwrite new business on favorable terms, and achieve target operating results. Increased competition, including new market entrants and the deployment of alternative capital, could reduce premium rates, depress retention, and limit growth opportunities, any of which could materially and adversely affect our business, financial condition, results of operations, and cash flows. The insurance industry is historically cyclical, which may cause Vantage’s results to vary materially from period to period. The property and casualty insurance industry has historically been cyclical, alternating between “soft” markets characterized by excess underwriting capacity, price competition, and falling premium rates and “hard” markets characterized by capacity shortages, increased premium rates, and improved profitability. This cyclicality is often more pronounced in the excess-and-surplus-lines market in which Vantage participates. We cannot predict the timing or duration of changes in the market cycle, which depend on factors largely outside our control, including the actions of competitors, general economic conditions, the frequency and severity of catastrophes, and capital flows into and out of the industry. As a result, Vantage’s gross written premium, underwriting profitability, and overall results may fluctuate materially from period to period, and past results should not be considered indicative of future performance. Catastrophic events expose Vantage to large insured losses and may increase the cost or reduce the availability of reinsurance. Vantage is exposed to insured losses arising from natural and man-made catastrophes, including hurricanes, severe convective storms and tornadoes, windstorms, earthquakes, hailstorms, wildfires, floods, terrorism, riots, and pandemics. The frequency and severity of catastrophic events are inherently unpredictable, and changing weather patterns and climate change may increase both. A single catastrophe or a series of catastrophes could result in insured losses materially in excess of Vantage’s estimates and could exhaust the reinsurance capacity Vantage has secured. Catastrophes can also cause widespread market disruption that increases the cost, or reduces the availability, of reinsurance for subsequent periods. As described elsewhere in the 2025 Annual Report, the Company is also separately exposed to physical damage from catastrophes at its real estate properties; the risks described in this factor are distinct and relate to Vantage’s insured-loss exposure. Vantage’s investment-portfolio results are subject to equity-price, interest-rate, concentration, and other market risks, and adverse investment results may coincide with underwriting losses. A significant portion of Vantage’s revenue and earnings derives from its investment portfolio, which consists primarily of short-term U.S. Treasury securities (including cash equivalents) and common equities, and which may also include other asset classes. The performance of this portfolio is subject to a variety of risks, including liquidity risk, equity-price risk (including market volatility and declines in the value of common equity holdings), concentration risk (to the extent the portfolio holds a limited number of equity positions), interest-rate risk (including the effect of rate changes on the fair value of Treasury holdings and on net investment income), credit risk (to the extent applicable), sovereign and political risk, and risks arising from extreme weather, geopolitical events, and other catastrophic conditions. Realized and unrealized investment losses, reduced net investment income, and impairments may occur, and may occur at the same time as significant underwriting losses, compounding the adverse effect on our business, financial condition, results of operations, and cash flows. A downgrade or withdrawal of Vantage’s A.M. Best financial-strength rating could materially impair its ability to write business. A.M. Best and other rating agencies assign financial-strength ratings to insurance and reinsurance companies. These ratings reflect the rating agency’s assessment of the insurer’s ability to meet its ongoing obligations to policyholders and are an important factor in the decisions of brokers, reinsurers, and insureds regarding whether to place business with a particular carrier. A.M. Best has assigned Vantage’s principal insurance subsidiaries a financial-strength rating of A- (Excellent) with a positive outlook. A.M. Best periodically reviews this rating and may revise it downward, place it under review, or withdraw it based on its assessment of factors that include balance-sheet strength, operating performance, business profile, and enterprise risk management. A downgrade or withdrawal of Vantage’s financial-strength rating could cause distribution partners, reinsurers, and insureds to place or accept business with more highly rated competitors, could increase the cost or reduce the availability of reinsurance to Vantage, and could limit or prevent Vantage from writing new HHH 2026 FORM 10-Q | 74 Table of Contents and renewal contracts. These risks are distinct from the risk of an adverse change in our corporate credit ratings, which is addressed separately in the 2025 Annual Report. Vantage manages alternative reinsurance platforms and segregated-account vehicles, which exposes Vantage to additional regulatory, and counterparty risks. Certain of Vantage’s subsidiaries provide management and administrative services to AdVantage Reinsurance Bermuda Ltd., a collateralized insurer and segregated-account company that constitutes an alternative reinsurance platform operating as part of Vantage’s partnership capital unit. In providing these services, these subsidiaries owe legal duties and obligations, including reporting obligations, to the vehicle and, indirectly, to third-party investors that provide capital to its segregated accounts. The management of these structures is subject to complex and evolving laws and regulations, and a failure of personnel to adhere to established policies and procedures—even if inadvertent—could result in regulatory action, contractual liability, or other losses. In addition, Vantage’s ability to write certain lines of business depends in part on the capital provided by these third-party investors, and the loss, alteration, or reduction of this capital support, or Vantage’s inability to attract additional capital for new or existing segregated accounts, could reduce Vantage’s fee income and limit underwriting capacity. Any of these outcomes could materially and adversely affect our business, financial condition, results of operations, and cash flows. National and global economic conditions, including inflation, recession or the perception that recession may occur, and national and international socio-political events, could materially and adversely affect Vantage’s business. Factors, such as business revenue, economic conditions, the volatility and strength of the capital markets, and inflation may affect Vantage’s ability to receive the appropriate rate for the risk Vantage insures for its policyholders and may adversely affect the number of policies it can write and its opportunities to underwrite profitable business. Inflation and increased international trade tariff-related loss costs could significantly impact Vantage’s claims severity across multiple lines of business and cause adverse reserve development. An economic downturn could also lead to increased credit and premium receivable risk, failure of reinsurance counterparties and other financial institutions, limits on Vantage’s ability to issue new debt, reduced liquidity, and declines in Vantage’s investments' fair value and financial strength ratings. These potential events and other economic factors could adversely and materially affect our business, results of operations, financial condition, and growth. Ongoing wars and conflicts continue to impact global economic, banking, commodity, and financial markets by exacerbating ongoing economic challenges, including inflation and supply chain disruption, which influence insurance loss costs, premiums, and investment valuation. Changes in U.S. international trade policies and tariffs, particularly with large trading partners like Canada, China, and Mexico, could increase loss costs for materials and parts used in certain claims. FINANCIAL RISKS The Company is dependent on the operations and funds of its subsidiaries, including The Howard Hughes Corporation and Vantage. The Company has no business operations of its own, and the Company’s only significant assets are the outstanding equity interests of its subsidiaries, including The Howard Hughes Corporation (HHC) and Vantage and its subsidiaries. As a result, the Company relies on cash flows from its subsidiaries, including HHC and Vantage, to meet its financial obligations, including to service any debt obligations that the Company may incur from time to time in the future. Legal and contractual restrictions in agreements governing future indebtedness of any of the Company’s subsidiaries, as well as the financial condition and future operating requirements of any such subsidiaries, in each case, including HHC and Vantage, may limit such subsidiaries’ ability to distribute cash to the Company. In addition, dividends and other distributions from Vantage’s insurance subsidiaries to Vantage, and ultimately to the Company, are subject to insurance regulatory requirements administered by the Bermuda Monetary Authority and U.S. state insurance departments, which limit such distributions to amounts derived from earned surplus (or comparable measures) and may require prior regulatory notice or approval. If HHC, Vantage, or any of the Company’s other subsidiaries is limited in its ability to distribute cash to the Company, or if the earnings or other available assets of the Company’s subsidiaries are not sufficient to pay distributions or make loans to the Company in the amounts or at the times necessary for the Company to meet its financial obligations, then the Company’s business, financial condition, cash flows, results of operations, and reputation may be materially adversely affected. HHH 2026 FORM 10-Q | 75 Table of Contents Tax increases and changes in tax rules may adversely affect our financial results. As a company conducting business with physical operations throughout North America, we are exposed, both directly and indirectly, to the effects of changes in U.S., state, and local tax rules, as well as changes in Bermuda tax laws, regulations, administrative guidance, and interpretations applicable to us. Taxes for financial reporting purposes and cash tax liabilities in the future may be adversely affected by changes in such tax rules. We are also subject to U.S. tax rules of particular significance to international insurance and reinsurance groups, including the base-erosion-and-anti-abuse-tax, and related-person-insurance-income rules. These rules, and the related U.S. Treasury regulations and Internal Revenue Service (IRS) guidance, Bermuda laws and regulations, and related guidance or interpretations issued by Bermuda authorities, are subject to change (in some cases on a retroactive basis), and any such change could adversely affect our effective tax rate, our cash tax obligations, or the structure of our intercompany insurance and reinsurance arrangements.