Howard Hughes Holdings is making its clearest break yet from its real estate focus, agreeing to buy specialty insurer Vantage Group Holdings in a $2.1 billion deal that anchors its shift to a diversified company.
The Woodlands-based firm said Thursday that it will acquire Bermuda-based Vantage, a specialty insurance and reinsurance firm backed by Carlyle and Hellman & Friedman, the Houston Business Journal reported. The deal is expected to close in the second quarter of 2026, and represents the first major operating business to sit alongside Howard Hughes’ master-planned communities.
For Howard Hughes Executive Chairman Bill Ackman, the deal puts real money behind a long telegraphed strategy. Ackman, whose Pershing Square entities bought a 47 percent stake in Howard Hughes in May, said he wants to turn the company into a “modern-day Berkshire Hathaway,” using steady real estate cash flow to fuel investments beyond property. That deal included Pershing Square agreeing to invest $900 million in Howard Hughes, as well as an investment in 9 million newly issued shares of Howard Hughes for $100 apiece.
Vantage gives Howard Hughes a firm with immediate scale. Founded in 2020, the insurer wrote $1.2 billion in net premiums in the 12 months ended Sept. 30, split roughly into 60 percent specialty insurance and 40 percent reinsurance. The company employs about 370 people and reported book value of $1.3 billion as of late September.
Under the deal structure, Howard Hughes will acquire full legal ownership of Vantage now, with the ability to increase its ownership to 100 percent over time. Pershing Square will manage Vantage’s investment assets on a fee-free basis, a key lever Ackman and his team believe can drive long-term value. The focus, the company said, will be underwriting discipline and profitability, rather than premium growth for its own sake.
The move builds on those changes set in motion earlier this year, when Pershing Square installed its chief investment officer, Ryan Israel, into a newly created CIO role at the company. CEO David O’Reilly and the existing leadership team remain in place, now overseeing a broader mandate.
Howard Hughes’ real estate arm, Howard Hughes Communities, controls master-planned developments across Texas, Nevada, Hawaii, Maryland and Arizona. Pershing Square has argued those assets are nearing a phase where they generate excess cash beyond what’s needed for development, freeing capital for outside investments like Vantage.— Eric Weilbacher
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