Ackman Bets $2.1 Billion on Insurer to Jump-Start Howard Hughes Strategy

Howard Hughes Holdings Inc. said it has agreed to buy Bermuda-based specialty insurer Vantage Group Holdings for $2.1 billion in cash and stock, a move the real estate developer says will anchor a plan to build a diversified holding company with an insurance core. Ackman said the strategy mirrors Warren Buffett’s Berkshire Hathaway approach, aiming to create a platform capable of growing capital beyond land development. "Learning from Mr. Buffett, we’ve taken a similar approach and began a search either for a management team to build a business around, or for an existing company we could acquire at a price that made sense and use as the core of this platform," Ackman said.

The deal values Vantage at roughly 1.5 times its estimated year-end 2025 book value, with closing targeted for the second quarter of 2026, pending the usual regulatory sign-offs. Howard Hughes said it will fund the purchase with a combination of cash on hand and up to $1 billion from Pershing Square through newly issued preferred stock. The preferred shares are non-interest bearing and non-voting, meaning the company won’t owe Ackman regular interest and will not cede voting power to the investor. Investors greeted the news with optimism, sending Howard Hughes shares higher by about 3% after the announcement.

Howard Hughes is pursuing a pivot beyond real estate development, a shift that Ackman has described as accelerating the company’s ability to compound capital across a broader portfolio. The Vantage acquisition is meant to speed up a transformation already in motion, including the spinoff of Seaport Entertainment Group last year as part of a broader plan to build a structure capable of sustaining growth beyond land sales.

Vantage Group Holdings is Bermuda-based and specializes in property and casualty insurance products, an asset the company intends to leverage as the cornerstone of Howard Hughes’s new platform. The deal aligns with Ackman’s stated goal of creating a long-term, diversified holding company anchored by an insurance business, rather than relying solely on land development for value.

Howard Hughes — a 2010 spinoff tied to General Growth Properties’ bankruptcy — built its fortune around owning large tracts of land, selling plots to homebuilders and developing master-planned communities with homes, offices, shops and amenities. Its portfolio includes major projects such as The Woodlands and Bridgeland outside Houston and Summerlin in Nevada. Ackman chaired the company from 2010 to 2024, then returned as executive chairman in May 2025 after Pershing Square boosted its stake to about 47%. The Vantage buy is the latest step in a broader push to create an investment platform able to compound capital beyond real estate holdings.

The market response has been modestly positive, with investors signaling support for the strategic direction even as execution risk remains. The deal’s financing structure — combining cash on hand with up to $1 billion of Pershing Square capital via preferred stock — is designed to provide a balance of liquidity and control for Howard Hughes while limiting immediate cash outlays. The company also noted that the preferred issuance would be non-voting, preserving current governance dynamics while enabling the new insurance-focused platform to emerge.

Ackman’s leadership has been central to the company’s transformation plan. Since taking executive chairman role in 2025, he has steered a push to broaden Howard Hughes’s portfolio beyond land development, leveraging Pershing Square’s capital and deal-making approach to assemble a diversified franchise. The Seaport Entertainment Group spinoff completed last year removed a non-core asset from the portfolio, allowing management to concentrate on a platform designed to compound capital across multiple lines of business. The Vantage transaction signals how the company envisions creating scale in adjacent industries while maintaining a disciplined capital-allocation framework.

As the regulatory review progresses, observers will watch how the integration unfolds and whether the insurance platform can reach the scale necessary to underpin Howard Hughes’s long-term growth ambitions. The company has stressed that the transaction is intended to serve as a foundational element for a broader holding company strategy rather than a one-off acquisition. If successful, the deal could illustrate a concrete path for real estate developers to build diversified platforms anchored by insurance and other financial businesses, guided by a leadership team that blends practical real estate insight with investment-management discipline.