Bill Ackman’s Pershing Square Holdings hedge fund ended 2025 with a 20.9 percent gain, even after losing money during the fourth quarter. It was the fourth time since 2020 that the fund has managed to post a more than 20 percent return.
Ackman made bank by following the two dominant trends in the market last year: AI and anything related to President Donald Trump. The strong year also gave him an opportunity to advance one of his long-term goals: building an empire along the lines of his role model — Warren Buffett — by buying a property casualty insurance company as Buffett did.
In terms of performance, by far his biggest winners were Fannie Mae and Freddie Mac, the two government-sponsored enterprises he has held onto since 2013 despite losing money in them until the recent Trump plan to take them public. The two mortgage giants were up more than 100 percent last year on Trump’s embrace, but Ackman now wants them to stay in conservatorship for fear an IPO would dilute his ownership.
“The businesses are in a position to be listed on the New York Stock Exchange,” he told investors in November. “Importantly, we think they should stay in conservatorship.”
Ackman no longer discloses the size of his stakes, but at one point he owned about 10 percent of the 20 percent of each firm not owned by the government, or about 2 percent.
Next up on the leaderboard were his relatively new investments in stocks that benefited from the AI mania: Amazon, Alphabet, and Uber. Alphabet was the runaway winner of the three, rising 67 percent for the year as Google’s Gemini gained market share from ChatGPT.
As of its most recent 13F filing based on Sept. 30 holdings, Pershing Square had a $2.7 billion stake in Alphabet. Some of those shares have gained more than 200 percent since purchased in 2023.
Amazon was up about 9 percent last year while Uber gained about 35 percent.
Ackman has long wanted to do more than run a hedge fund. An initial effort to grow his empire by starting a U.S. closed-end fund for retail investors that could be listed on the NYSE — which was initially estimated to garner some $25 billion — failed spectacularly in 2024 when investor interest fizzled.
But he took a major step toward expanding his enterprise late last year when Howard Hughes Holdings, a real estate company that Pershing Square controls, announced it would buy Vantage Group Holdings, an insurance company owned by private equity firms The Carlyle Group and Hellman & Friedman. Howard Hughes will pay $2.1 billion for the property and casualty insurance and reinsurer.
When the deal closes this year, it could transform Howard Hughes into a diversified holding company along the lines of Warren Buffett’s Berkshire Hathaway. Buffett was such a role model of Ackman’s that the Pershing Square founder was once called “Baby Buffett.”
Pershing Square increased its stake in Howard Hughes to 46.9 percent last year, gaining control with a $900 million investment in May and capping its voting power at 40 percent. Ackman is its executive chairman.
Howard Hughes stock, however, fell on the insurance company deal and only managed a gain of about 4 percent in 2025. The stock has been on a mostly downward path since its highs in 2014, falling almost 50 percent since then despite Ackman’s continued stock purchases over the years.
Howard Hughes also increases Pershing Square’s total AUM to $31 billion, according to Pershing Square disclosures. The hedge fund manages about $19 billion.
