No matter how hard he tries, Billy Ackman will not be the next Warren Buffett

Billy Ackman wants to be Warren Buffett so bad. That’s the pitch. That’s the ambition. And that’s the problem. Because if you have to tell the world you’re building a new Berkshire Hathaway, chances are you’re not.

Just two days after Warren announced that he was gonna step down from Berkshire, Billy rolled out his playbook: use Howard Hughes Holdings, a real estate bundle with $4.2 billion in market value, and turn it into his own investment empire. It was a move he teased in a letter months earlier, calling it a shot at building a “modern-day Berkshire Hathaway.”

The structure is simple: Howard Hughes will stop focusing on real estate development and start buying stakes in other companies. Billy’s hedge fund, Pershing Square, is injecting $900 million in fresh capital to make this happen, taking its stake in the company to 47%.

Billy bets big, but his track record is messy

Howard Hughes owns massive suburban master-planned communities across Nevada, Texas, and Maryland. They’ve got homes, shops, churches, schools, even golf courses — all packaged into neatly managed enclaves like The Woodlands.

Billy has been behind the company since it was carved out of General Growth in 2010, following his $1.5 billion gain from scooping up shares in the middle of that company’s bankruptcy. He used those profits to launch Howard Hughes, promising a bigger vision. But after more than a decade of slow performance, it’s clear that Howard Hughes never became what Billy hoped.

He now wants to reboot the company. And step one is building an insurance arm to replicate the Berkshire strategy of using premiums to fund deals. “Unlike the state of the textile industry in America in 1965,” Billy told The Financial Times, “the state of building cities in places where people live in the US in 2025 is actually an amazing business.”

But his results at Howard Hughes suggest otherwise. From 2010 to 2024, Billy served as the company’s chair. During that time, he spent close to $1 billion on an attempt to overhaul the South Street Seaport in New York City.

The entertainment-and-dining complex failed to deliver profits, and one major shareholder pinned the failure directly on Billy, saying, “It is all on Ackman in terms of the value destruction at the Seaport.”

Despite that, Billy claims credit for smart acquisitions, including deals to buy out partners in Howard Hughes communities. He insists the new plan will boost the company’s credit rating and diversify its income.

But the market hasn’t bought in. Since the announcement, shares of Howard Hughes have risen around 6% to $71 — better than the S&P 500 in that same time, but far below the $100 per share Billy paid using cash from outside investors.

Billy’s fee structure and political agenda go against the Warren Buffett way

Now Warren has never taken a management fee, but Billy’s out here charging $15 million a year, plus 1.5% on any returns that beat inflation. He says that’s better than fees in other Pershing Square funds, and investor James Elbaor of Marlton agrees.

James called the pricing “very fair” and praised the deal’s impact on Howard Hughes’ credit profile. But even supporters can’t change the fact that this setup looks nothing like Warren’s.

And then there’s politics. Warren has stayed out of it for seven decades. Billy never does. He’s jumped between parties over the years. He donated to Democrats like Chuck Schumer, Richard Blumenthal, and the DNC.

In 2016, he endorsed Michael Bloomberg, then voted for Donald Trump. He backed Dean Phillips in the 2024 primaries and appeared with him in a forum alongside Elon Musk, where Phillips even floated Billy for a Cabinet role.

After Phillips dropped out, Billy switched to supporting Robert F. Kennedy Jr. Then in April 2024, he said he wouldn’t back Joe Biden because of what he called a “lack of support” for Israel. In July, right after Trump survived an assassination attempt, Billy publicly endorsed him again.

That level of political hopping is completely opposite of what Warren stood for. Warren didn’t chase headlines. Billy lives in them. And in a time when investors are already nervous about volatility triggered by Trump’s economic policies, Billy’s aggressive pivot at Howard Hughes just adds more questions.

Billy insists the starting point for Howard Hughes is stronger than Berkshire’s was in the 1960s. “It is the opposite of a disadvantage,” he said. But words don’t replace time, reputation, or trust. Warren built quietly. Billy builds loudly.

Warren never begged anyone to believe in the vision. Billy wrote a letter explaining it before he even had a deal. That’s the difference. And that’s why Billy will never be Warren.