HHH 10-K & 10-Q changes, risk factors and insider trading

HHH 2025 FORM 10-K | 11 casinos, land-based casinos, video lottery, sweepstakes, and poker machines, many of which are located outside of Las Vegas. Furthermore, competition from internet lotteries, sweepstakes, and other internet-wagering gaming services, which allow their customers to wager on a wide variety of sporting events and play Las Vegas-style casino games from home or in non-casino settings, could negatively impact the population in the Las Vegas area.

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Village, are located in regions that could be affected by increases in sea levels, the frequency or severity of hurricanes and tropical storms, or environmental disasters, whether such events are caused by global climate changes or other factors. Additionally, adverse weather events can cause widespread property damage and significantly depress the local economies in which the Company operates and have an adverse impact on the Company’s business, financial condition, and operations.

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In particular, recent executive actions and trade policies implemented or proposed by the current U.S. administration, including the imposition or threat of significant tariffs on imported goods, including construction materials and other critical

In 2024, we completed the spinoff of Seaport Entertainment Group Inc. into an independent publicly traded company, and we may not achieve some or all of the Spinoff’s expected benefits.

On July 31, 2024, we completed the spinoff of Seaport Entertainment Group Inc. (the Spinoff), as an independent, publicly traded company. In structuring and completing the Spinoff, we anticipated certain benefits that may not be achieved, may be delayed, or may be less advantageous than we anticipate for a variety of reasons. Following the Spinoff, we may be more susceptible to market fluctuations and other adverse events than prior to the Spinoff, and our business is less diversified than the combined businesses prior to the Spinoff.

Pershing Square beneficially owns approximately 46.7% of our outstanding common stock as of February 12, 2026. Mr. William Ackman, the Chief Executive Officer of Pershing Square, is the Executive Chairman of our board of directors. Additionally, Mr. Ryan Israel, the Chief Investment Officer of Pershing Square, is our Chief Investment Officer and a member of our board of directors, and Mr. Ben Hakim, the President of Pershing Square, is a member of our board of directors.

On May 5, 2025, HHH entered into a Share Purchase Agreement (Purchase Agreement), by and between HHH and Pershing Square Holdco, L.P. (PS Holdco), pursuant to which HHH sold to PS Holdco 9,000,000 newly issued shares of the Company’s common stock for an aggregate purchase price of $900 million. In connection with the Purchase Agreement, we also entered into several other agreements with Pershing Square, including a Services Agreement and a Shareholder Agreement.

Pursuant to the terms of the Services Agreement, Pershing Square will support the Company’s new diversified holding company strategy by providing services to the Company, such as (i) investment advisory services, (ii) making recommendations with respect to hedging, balance sheet optimization, and capital allocation, (iii) executing transactions, (iv) assisting the Company with business and corporate development functions, (v) making voting recommendations for the Company’s investments, (vi) assisting with and advising on fundraising, (vii) monitoring operations of the Company and its investments, subject to the day-to-day authority and responsibility of management of the Company, (viii) providing recommendations for persons to serve as designees or deputies of the Chief Investment Officer, (ix) engaging and supervising third-party service providers, (x) making dividend payment recommendations, and (xi) providing other services as may be agreed upon. The Services Agreement has an initial ten-year term and will have successive renewal terms of ten years. The Company pays Pershing Square a quarterly base advisory fee of $3.75 million and a quarterly variable advisory fee equal to 0.375% of the excess value of the quarter-end stock price of the Company’s common stock minus

HHH 2025 FORM 10-K | 15 the reference price of $66.15, multiplied by existing share count as of the transaction date, which will not increase with the issuance of new shares of common stock.

Among other things, the Shareholder Agreement provides that, at any meeting of stockholders where directors are to be elected, (a) so long as PS Holdco, Pershing Square and their respective affiliates, including investment funds managed by one or more affiliates (collectively, the Purchaser Group), beneficially own at least 17.5% of the outstanding shares of Common Stock on a fully diluted basis, PS Holdco may nominate for election a number of directors equal to 25% of the total number of members of the Board as constituted after giving effect to such election, rounded up (e.g., three directors in the case of an 11-member Board) (such director, a PS Board Designee), and (b) so long as the Purchaser Group beneficially owns less than 17.5% but at least 10% of the outstanding shares of Common Stock on a fully diluted basis, PS Holdco may nominate for election a number of PS Board Designees equal to 10% of the total number of members of the Board as constituted after giving effect to such election, rounded up (e.g., two directors in the case of an 11-member Board). If the Purchaser Group owns less than 10% of the outstanding shares of Common Stock on a fully diluted basis, PS Holdco no longer has the right to nominate any PS Board Designees. William A. Ackman, Ben Hakim, and Ryan Israel currently serve as the PS Board Designees.

Our recent shift in business strategy, including the planned acquisition of Vantage, will create additional and different risks than those we face in our existing real estate business.

Since the announcement of our transaction with Pershing Square in May 2025, we have been executing on our strategy to become a diversified holding company, including by entering into the Purchase and Sale Agreement with Vantage on December 17, 2025, pursuant to which the Company will acquire Vantage for a purchase price of $2.1 billion (subject to certain adjustments). As part of this strategy, we expect to acquire controlling stakes in high-quality, durable growth public and private operating companies while continuing to invest in and grow our core real estate development and Master Planned Communities business. In embarking on this changed strategy, we are subject to risks such as being unable to identify and consummate transactions (including the Vantage Transaction) as part of the new strategy, as well as risks inherent in acquiring or making investments in operating companies, especially companies in industries unrelated to our existing real estate business. Sources of risk arising from these types of transactions include financial, accounting, tax, and regulatory challenges; difficulties with integration, business retention, execution of strategy, unforeseen liabilities or market conditions; and other managerial or operating risks and challenges. Any future transactions could also subject us to risks such as failure to obtain appropriate value, post-closing claims being levied against us, and disruption to our other businesses during the negotiation or execution process or thereafter. Risk-mitigating provisions that we put in place in the course of negotiating and executing these transactions, such as due diligence efforts and indemnification provisions, may not be sufficient to fully address these risks and contingencies.

We may be unable to realize the anticipated benefits of the transactions with Pershing Square, the Vantage Transaction, and/or our new strategy, which could adversely impact our financial condition, results of operations, cash flows, the quoted trading price of our securities, and our ability to satisfy our debt service obligations.

HHH 2025 FORM 10-K | 16 other debt agreements, we may need to incur substantial additional indebtedness from time to time, including project indebtedness for developments by our subsidiaries. If we incur additional indebtedness or experience an adverse change in interest rates, the risks related to our level of indebtedness could intensify. Specifically, an increased level of indebtedness could have important consequences, including:

HHH 2025 FORM 10-K | 17 agreements or other obligations accelerate the maturity of those obligations, we cannot assure that we will have sufficient assets to satisfy our obligations under the notes or our other debt.

Adverse changes in our credit ratings could increase our financing costs and limit market access.

We and certain of our subsidiaries may be evaluated by one or more nationally recognized credit rating agencies. Ratings reflect each agency’s assessment of factors such as liquidity, leverage, capital structure, cash flow stability, asset quality, business profile, corporate governance, and market conditions, and they can be downgraded, placed on negative watch, revised in outlook, or withdrawn at any time. A downgrade or other adverse action, or the announcement of a review, could increase interest rates and fees on new or existing debt; narrow the pool of investors willing or permitted to invest in our securities; require additional collateral, tighter covenants, shorter maturities, or other unfavorable terms; and reduce the trading price and liquidity of our securities. These outcomes could raise our overall cost of capital, constrain access to bank and capital markets, reduce financial flexibility, and impair execution of our strategy and our ability to meet obligations, any of which could materially adversely affect our business, financial condition, results of operations, and cash flows.

We may be unable to refinance our indebtedness on favorable terms, or at all.

We have a substantial amount of indebtedness, a significant portion of which will mature in the coming years. Our strategy assumes continued access to the debt capital markets and other financing sources to refinance existing indebtedness, including property‑level mortgage loans, construction and development facilities, and unsecured or recourse borrowings, often before maturity. Our ability to refinance our indebtedness on favorable terms, or at all, depends on factors beyond our control, including conditions in the credit and capital markets (such as interest rates, spreads, and lender appetite for real estate and construction lending); our leverage, liquidity, interest coverage and credit ratings; the performance and values of properties securing our debt and our broader portfolio; changes in banking and other financial regulations; and broader macroeconomic, geopolitical, and industry developments.

If we cannot refinance maturing indebtedness on acceptable terms, we may be forced to seek alternative financing on less favorable terms, use more of our available liquidity, sell assets, on disadvantageous terms or at unfavorable times in the market, delay or cancel development, redevelopment, or other capital projects, or issue equity or equity‑linked securities that could be dilutive to existing stockholders. Even if refinancing is available, it may be at higher interest rates or subject to more restrictive covenants, which could increase our interest expense, reduce our financial flexibility, and constrain our ability to invest in our existing properties and development pipeline or pursue new investment opportunities. Failure to refinance, repay, or otherwise address maturing indebtedness could lead to defaults, acceleration, foreclosure on collateral, and potential cross defaults or cross accelerations, any of which could materially adversely affect our business, financial condition, results of operations, cash flows, and ability to service our debt.

HHH 2025 FORM 10-K | 18 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.

General Howard Hughes Holdings Inc. (HHH or the Company) is a holding company that owns a real estate development subsidiary, The Howard Hughes Corporation (HHC). Through HHC, the Company 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. References to HHH, the Company, we, us, and our refer to Howard Hughes Holdings Inc. and its consolidated subsidiaries, which includes The Howard Hughes Corporation, unless otherwise specifically stated. References to HHC or Howard Hughes Communities refer to The Howard Hughes Corporation and its consolidated subsidiaries unless otherwise specifically stated.

In 2025, the Company began executing a long-term strategy to transition from a pure-play real estate company to a diversified holding company. On May 5, 2025, the Company issued 9,000,000 shares of newly issued common stock to Pershing Square for an aggregate purchase price of $900 million (Pershing Square Issuance). In connection with the investment, the Company and Pershing Square entered into related agreements, including a Services Agreement, Shareholder Agreement, Standstill Agreement, and Registration Rights Agreement. The Company intends to use the proceeds from the transaction to acquire or invest in operating businesses.

As previously disclosed in our Current Report on Form 8‑K filed on December 18, 2025, the Company entered into a definitive agreement to acquire 100% of Vantage Group Holdings Ltd. (Vantage), a privately held specialty insurance and reinsurance company, for cash consideration of approximately $2.1 billion. The transaction remains subject to regulatory approvals and other customary closing conditions, and is expected to close in the second quarter of 2026. To support the funding of the acquisition, the Company also entered into an equity commitment letter with Pershing Square Holdings, Ltd. under which Pershing Square committed to purchase up to $1.0 billion of the Company’s preferred stock, prior to and contingent upon the closing of the Vantage acquisition. Over time, the Company will have the right, but not the obligation, to repurchase the preferred stock during specified periods and upon certain triggering events. The acquisition is expected to be funded through the Company’s cash on hand, and proceeds from the issuance of the preferred stock.

Changes for monetary amounts between periods presented are calculated based on the amounts in thousands of dollars stated in our 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.

2025 Results During 2025, we delivered exceptional results across our core business lines. Operating Assets net operating income (NOI) and MPC earnings before taxes (EBT) both reached record highs, while our condo and strategic development activities extended the runway for future growth.

In Strategic Developments, Ward Village had another strong year, closing 690 units at Ulana Ward Village, a workforce tower that generated $369.5 million of condominium revenues at a break even gross margin, which is consistent with our typical target for workforce towers. Pre-sales activity for our under construction condominiums progressed, and these projects were 93% pre-sold at year end and represent more than $1.9 billion of future contracted revenue. Leasing activity at The Launiu remained strong and we launched pre-sales for two new Ward Village condominiums, Melia and ‘Ilima in June 2025, with 66% of the units at these predevelopment towers pre-sold at year end representing $2.0 billion of future contracted revenue. Future contracted revenues will be recognized as projects are completed.

2026 Outlook Proceeding into 2026, we maintain a positive long-term outlook for our businesses and believe we are well positioned to create value across cycles. We remain focused on maintaining liquidity, managing near‑term maturities, and allocating capital to the highest‑return opportunities across our business segments. Development spending will continue on a disciplined basis, and we will evaluate opportunities to recycle capital and enhance balance‑sheet flexibility as market conditions evolve.

Across our master planned communities, we expect demand for new homes, retail, and office space to remain resilient, supported by constrained inventories of existing homes, continued migration to our communities, and the quality and scale of our offerings. MPC EBT is expected to normalize in 2026 following a record year of land sales in 2025 and Operating Assets performance is expected to be stable to modestly positive. We expect condominium activity during the year to be driven primarily by The Park Ward Village, which is substantially pre-sold and positioned to contribute meaningful revenue and gross profit as it is delivered.

Additionally, the Pershing Square investment and the pending agreement to acquire Vantage mark important steps in broadening our strategic reach. We expect to make meaningful progress in 2026 toward building a durable foundation to compound long-term shareholder value across multiple platforms, while maintaining our focus on liquidity, disciplined capital allocation, and balance sheet flexibility. The Company’s expectations will be updated as applicable throughout 2026, and as additional information becomes available regarding the pending Vantage acquisition and its expected contribution to the consolidated business.

Our outlook is subject to risks and uncertainties, including those related to interest rates, capital markets conditions, general economic and housing trends in our key regions, and other factors described in Part I, Item 1A. Risk Factors and elsewhere in this Annual Report.

Overall –Net income from continuing operations decreased to $123.8 million in 2025, compared to net income of $285.2 million in the prior year. The year-over-year decrease was primarily attributed to a change in the product mix of condominium closings as we closed units at a workforce tower in the current year, compared to closing units at a luxury tower in the prior year, and the receipt of insurance proceeds in the prior year following the execution of a settlement agreement related to the construction defect claims at Waiea. These decreases were partially offset by an increase in residential acres sold in Summerlin.

–We continue to maintain a strong liquidity position with $1.5 billion of cash and cash equivalents, $515.0 million of undrawn capacity on our Secured Bridgeland Notes, and $686.6 million of undrawn lender commitment available to be drawn for property development, and limited near-term debt maturities.

–Operating Assets EBT increased $1.0 million, with a loss of $27.4 million in 2025, compared to a loss of $28.5 million in the prior year.

–Operating Assets NOI was $262.0 million in 2025, a $16.5 million increase compared to $245.5 million in the prior year.

–Office NOI increased $13.6 million, primarily due to strong leasing activity and abatement expirations at various properties in The Woodlands, Merriweather District, and Summerlin, most notably at 9950 Woodloch Forest, 6100 Merriweather, and 1700 Pavilion, partially offset by decreases related to lower occupancy at certain properties in The Woodlands, most notably at 3831 Technology Forest and Two Hughes Landing.

–Multifamily NOI increased $3.9 million primarily due to continued lease-up at Tanager Echo in Summerlin, Wingspan in Bridgeland, and Marlow in Merriweather District.

–In 2025, the Company completed the sale of four land parcels and retail spaces in Ward Village for total proceeds of $18.2 million, and a combined gain on sale of $14.4 million.

MPC –MPC EBT totaled income of $476.1 million in 2025, a $127.0 million increase compared to income of $349.1 million in the prior year.

–The increase in EBT was primarily due to higher residential land sales at Summerlin and Bridgeland, higher commercial land sales in The Woodlands, and lower equity losses at The Summit.

HHH 2025 FORM 10-K | 37 –Strategic Developments EBT totaled a loss of $13.9 million in 2025, a $296.7 million decrease compared to income of $282.8 million in the prior year.

–The decrease in EBT was primarily due to a decrease in condominium sales net cost of sales due to the change in the product mix of condominium closings as we closed units at a workforce tower in the current year, compared to closing units at a luxury tower in the prior year, and a decrease in other income related to accruing a charge for a legal judgment in Columbia in the current year, compared to the receipt of insurance proceeds for the Waiea remediation in the prior year. These decreases were partially offset by an increase in gain on sale of real estate assets due to a land swap in The Woodlands and the sale of a land parcel near Merriweather District in the current year.

–Leasing activity at The Launiu remained strong and we launched pre-sales for two new Ward Village condominiums, Melia and ‘Ilima in June 2025. During 2025, we contracted 283 pre-development units and as of December 31, 2025, 66% of the units at our three pre-development towers are under contract.

–In 2025, we placed three properties in service, including Grogan’s Mill Retail, a retail property in The Woodlands; One Bridgeland Green, an office property in Bridgeland; and 1 Riva Row, a multifamily property in The Woodlands. These properties represent 268 multifamily units and approximately 81,000 square feet of retail and office space.

–In 2025, we began construction on Memorial Hermann Medical Office, an office building in Bridgeland, and the redevelopment of 7 Waterway, an office building in The Woodlands. These properties represent approximately 237,000 square feet of office space.

Corporate –Net expenses related to Corporate income, expenses, and other items decreased $7.3 million compared to the prior year primarily due to a decrease in income tax expense, partially offset by an increase in general and administrative expenses, primarily related to the Pershing Square advisory fee and a strategic reduction in force in the current year.

Capital and Financing Activities –In 2025, our financing activity included draws on existing mortgages of $573.5 million, refinancings of $184.2 million, and repayments of $365.7 million. In addition, we repaid $198.0 million on the Secured Bridgeland Notes using the proceeds from the sale of Municipal Utility District (MUD) receivables. For additional information, refer to Note 9 - Mortgages, Notes, and Loans Payable, Net in the Notes to Consolidated Financial Statements under Item 8 of this Annual 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.

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.

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.

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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.

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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.

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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 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.

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.

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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.

HHH 2026 FORM 10-Q | 47 –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.

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.

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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.

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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.

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This increase to EBT was partially offset by the following: