Ever since Warren Buffett built Berkshire Hathaway around ownership of insurance companies, many have attempted to copy his approach. Unlike traditional insurance stocks, which seek to profit by investing insurance premiums in fixed-income instruments such as bonds, Buffett's approach entails investing float in stocks to generate superior long-term returns.
Investor Bill Ackman, through Howard Hughes Holdings (HHH -1.75%), or HHH for short, is the latest Wall Street titan to try to emulate this strategy. Not only that, but Ackman appears to be aiming to mimic the approach of another famed investment holding company.
Pershing Square Capital Management CEO Bill Ackman. Image source: Getty Images.
Ackman, Howard Hughes, and the Vantage Deal
Howard Hughes Holdings was formed in 2010, when then-bankrupt General Growth Properties spun off its real estate development business. Known for master-planned community developments like Summerlin, located outside Las Vegas, the company has slowly shifted its focus since Bill Ackman's involvement began in the late 2010s. First, by spinning off non-core real estate and other assets as Seaport Entertainment in 2024.
HHH Howard Hughes
NYSE · As of 4:00 PM ET 10/16/26
Then, in 2025, Pershing Square invested another $900 million in HHH, raising the fund's stake to 47%. Still working slowly, Ackman has only recently revealed his "master plan" for the master-planned communities company. In a recent interview with Bloomberg, Ackman discussed plans to transform HHH into both a Berkshire-style insurance holding company and an asset manager akin to Brookfield and Blackstone.
First, in a Berkshire-esque move, HHH acquired Vantage for $2.1 billion. Vantage's book value of around $1.8 billion represents much of this valuation. Alongside the purchase price of Vantage, Howard Hughes Holdings plans to invest between $2.5 billion and $3 billion of its excess free cash flow into the insurance unit over the next five years. HHH's goal is to have most of Vantage's excess capital invested in stocks. Ackman's Pershing Square will also manage Vantage's portfolio for free.
Second, alongside the Buffett insurance gambit, Ackman also seeks to juice up Howard Hughes' returns from real estate investments by taking on third-party investors and charging them management fees similar to those that Brookfield and Blackstone charge for their respective real estate investment management subsidiaries.
Is Howard Hughes Holdings a buy?
Howard Hughes Holdings shares surged around the time of Ackman's "Berkshire and Brookfield" remarks, but have since pulled back into the high-$60s per share, around the stock's book value of $66.95 per share. Yet while the stock may appear to have minimal downside at this price level, keep in mind that only time will tell whether Ackman's big plans pan out.
For one, it takes years, if not decades, to determine success in this area. Some insurers taking a Berkshire-style approach, like Markel Group, have beaten the market over a multidecade time frame; others, like Greenlight Capital, have lost money for investors.
In fact, Greenlight Capital, with excess funds managed by hedge fund billionaire David Einhorn, sounds very similar to what Ackman has in store for Howard Hughes Holdings. That's not to say a similar outcome is bound to happen, but consider this food for thought before investing just on the headlines alone.
Instead, consider waiting until some of the excitement surrounding Ackman's plans has simmered down. In the past, Howard Hughes Holdings has traded well below book value, and a similar situation could emerge again in the near term.
