Bill Ackman Is Tweeting Through It

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Listen: Bill Ackman Aspires to Warren Buffet Future After MAGA Makeover
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Last May, Bill Ackman made up his mind about the 2024 presidential election. He was approaching his 58th birthday and had pretty much achieved a hedge fund manager's version of nirvana: He was a billionaire; he was five years into his second marriage, with the love of his life; and, much to his delight, he'd amassed more than 1 million followers on X, with a profile that was starting to transcend the boundaries of finance. He was about to test how far.
On a trip to Los Angeles he met Elon Musk on the sidelines of the Milken Institute Global Conference, a kind of Davos-lite affair for the finance set. Ackman had helped support the Tesla Inc. chief executive officer's purchase of X (formerly Twitter), but up until then the two hadn't spent extended time together. They convened in a greenroom for roughly a half-hour, where the soon-to-become Department of Government Efficiency overlord encouraged him to support Donald Trump, before peeling off to deliver a fireside chat.
Days later, Ackman got a chance to sound out Trump himself, back in New York, over ravioli. Ackman was a longtime Democratic donor; in the 2024 presidential race, he'd already supported a series of would-be Trump challengers, including long-shot candidates Vivek Ramaswamy, former New Jersey Governor Chris Christie and Dean Phillips, who was then a Democratic representative from Minnesota. Ackman was adamant that the country needed alternatives to President Joe Biden, who he said back in 2023 was in decline and should step aside. For a billionaire, a second Trump term also had much to offer: the promise of lighter regulation and a business-friendly environment, for starters.
Ackman made his name as an activist investor—the type who will target a company, spotlight poor corporate leadership or meager results, apply pressure for dramatic change and, if it all works out, end up with a higher stock price and a personal windfall. He'd led overhauls of companies including Canadian Pacific Railway and Chipotle Mexican Grill Inc. But in recent years, after enduring some brutal losses, he gave up that combative investment approach and found a new release valve beyond the boardroom.
Ackman's successful battle against Ivy League leaders over diversity, equity and inclusion (DEI) policies culminated in the resignation of Harvard University President Claudine Gay (and became a prelude to the school's full-on war with the US government under Trump). Soon he announced the creation of a 'think and do tank' to fix the problems he sees in the world, including antisemitism and 'woke' groupthink in academia. He took full advantage of X's expanded character limit since Musk took over the social media platform, where he's now posted more than 10,000 times, to pontificate not just about investments and the economy but also on issues such as immigration and what he calls his ' psychological shorts '—companies he's betting against without any money on the line. 'I stopped being an activist in the corporate world, but I'm still an activist in the rest of the world,' Ackman told Bloomberg Businessweek in May.
Around the same time as he made up his mind politically, he was also angling to monetize his new memelord status and cement his legacy. He wanted to ascend from hedge fund manager to Wall Street legend, on par with his longtime idol, Berkshire Hathaway Inc. CEO Warren Buffett. Hedge fund managers buy pieces of companies, but they're at the whims of investors who might pull money out (or add more) at any moment. Berkshire's structure has insulated it from that kind of investor caprice—an attractive model to Ackman, who recently said he wanted 'to create our own, you might say, modern-day version of Berkshire Hathaway.'
What Buffett and Ackman had each built was very different. Buffett transformed a meager textile business into a giant insurer and investment firm that acquired some of the most well-known companies, today a vast conglomerate worth more than $1 trillion. Pershing Square Capital Management was a money management firm consisting primarily of a fund trading on the London Stock Exchange and holding just a handful of recognizable stocks, alongside a smaller hedge fund mirroring those investments. Their personas, too, couldn't be more different: Buffett has masterfully constructed an image of the folksy billionaire, still living in the house he bought in 1958 for $31,500. Ackman, who once rankled his Upper West Side neighbors with plans to expand his $22 million penthouse overlooking Central Park, is more conspicuous.
Ackman's plan—invoking Buffett in his pitch to investors—was to pull off one of the largest public offerings of all time, a fund of as much as $25 billion that would trade in the US. But in July the attempt imploded in spectacular fashion after Ackman was unable to raise the money. Even so, he plowed ahead with another idea: try to take over real estate developer Howard Hughes Holdings Inc. (a builder of master-planned communities in places such as Arizona, Nevada and Texas), which could give him a vehicle to buy majority stakes in other companies. It wasn't dissimilar to what Buffett originally did when he snapped up Fruit of the Loom, Benjamin Moore, Dairy Queen and the rest of his constellation of 189 operating businesses.
Many of Ackman's peers on Wall Street love to hate him, and they relish any comeuppance. The salt-and-pepper-haired, green-eyed investor has a reputation as a grandiose know-it-all. His trades range from the remarkably prescient (a $2.6 billion-plus win during Covid-19) to the completely disastrous (a $4 billion loss on Valeant Pharmaceuticals). In the secretive world of money management, it's generally viewed as counterproductive to declare your political views. Never mind that Buffett, a longtime Democrat who hasn't tweeted in nine years, pretty much stopped talking politics after Trump won in 2016. Ackman's vocal Trump pivot had further juiced his profile with two new sets: retail investors and culture warriors.
Bill Ackman's Winners and Losers
By the time he funneled $419,600 to the Trump 47 Committee in September, he'd more or less turned his X feed into a Trump praise generator. He tweet-bombed '33 Reasons to Vote for Trump,' followed by an appearance on the conservative podcast Triggernometry, where he shared his views on questions such as 'Is America in a healthy state?' (no), 'Are DEI policies ruining America?' (yes), 'Do we have a culture of cowardice?' (also yes) and 'Is Trump really that divisive?' (no). He was giddy with Musk retweets and weighed in on the conspiracy theory about immigrants eating house pets in Ohio, which wasn't popular with some members of his inner circle. Whitney Tilson, an old friend and former financier, slammed Ackman's pet-eating posts, according to text messages viewed by Businessweek. 'Bill is (of course) refusing to acknowledge Trump's (and his) mistake in spreading a fabricated, racist, xenophobic story,' wrote Tilson, who is running as a Democrat for mayor of New York City and declined to comment.
In the 12 months leading up to Trump's inauguration, Ackman added hundreds of thousands of X followers. Within a few days of Trump taking office, the fund manager was already touting the new president, who'd halted refugee arrivals, paused a pending US ban on TikTok, started the withdrawal from the Paris climate agreement and introduced an official memecoin. 'Other than the almighty, who has accomplished more in seven days than @POTUS Trump?' Ackman wrote on X. (Later he clarified: 'For those who didn't get it (of which there appear to be many), this was meant to be funny.')
Then came ' Liberation Day.' When Trump's sweeping tariffs triggered a $6 trillion selloff in global markets, Ackman shifted into his default setting—and started tweeting. But the tone was different. He compared the reciprocal tariffs to 'economic nuclear war' and urged the administration to consider a 90-day delay to avoid disaster. When Trump announced a pause of precisely that length a few days later—despite little evidence that the tariffs led to any trade victories for the US—Ackman shifted back to fealty-tweet mode. 'This was brilliantly executed by @realDonaldTrump. Textbook, Art of the Deal.' (He also backtracked on a searing post lobbed at Howard Lutnick, the Wall Street mogul-turned-commerce secretary, accusing him of standing to benefit if the 'economy implodes.') By then the Ackman memes had already begun circulating, including one of the financier in a latex suit with a leash. Another had him as a factory worker for Nike Inc., one of the companies his fund owns, with the words 'after his savior Trump bankrupts him.'
In early May one piece of Ackman's Buffett-esque plan came together. After four months of negotiations, he closed his Howard Hughes deal, increasing Pershing Square's stake in the company to 47%. When Ackman announced it, he'd just returned from Berkshire's annual meeting in Omaha, Nebraska, where thousands of Buffett superfans had gathered to hear from the investment guru. The meeting was dominated by Buffett's bombshell announcement that, after six decades, he'd finally step down as Berkshire's CEO at the end of 2025.
The timing might have seemed fortuitous to Ackman, at least as some sort of spiritual handoff. As the market haltingly approaches its February record high, Buffett's net worth has climbed by $13.6 billion this year. His investors have also been winners in the early days of Trump's second term, with Berkshire Hathaway shares rising 11% through May. Meanwhile, holders of Ackman's London-listed Pershing Square Holdings fund are flat on the year, even though the underlying holdings are up in line with Buffett's returns. The odds aren't necessarily in Ackman's favor, either: When Buffett bought Berkshire in 1965, it was the middle of the post-World War II economic boom. Economists today see the odds of a recession at 40%. Meanwhile, to really build the next Berkshire, Ackman still needs an insurance company for the same reason Buffett has one: the consistent cash it generates.
Ackman is undaunted, though. He recalls an early prophecy from the Oracle of Omaha himself. He first met Buffett almost 30 years ago, when Ackman was nothing more than a young Wall Street striver. The men, introduced by Buffett's then-wife, were next to each other in a buffet line of a symposium in New York, where the legend was the guest of honor. Ackman, a health fanatic, remembers two things: Buffett piling his plate high and salting everything excessively, right down to his fudge brownie, and Buffett telling him, 'You're going to do better than me, because you are starting small.' That, anyway, is how Ackman remembers it.
As for Buffett's thoughts on where Ackman has ended up, the 94-year-old declined to comment. But in recent years he's been a vocal skeptic of hedge funds at large. 'There's been far, far, far more money made by people in Wall Street through salesmanship abilities,' Buffett said at Berkshire's annual meeting in 2016, 'than through investment abilities.'
In 1995, from a cramped suite of offices in Manhattan, a twentysomething Ackman plotted his first big deal as a hedge fund manager. An upper-middle-class kid from the wealthy New York suburb of Chappaqua, he'd briefly worked for his father, who helped organize the financing for some of the city's top real estate developers. Now, only a few years after teaming with a friend from Harvard and raising $3 million from a handful of investors to start the investment fund Gotham Partners, they set out to do something audacious: go up against some of the world's richest families and real estate tycoons to try to win control of Rockefeller Center.
Mitsubishi Estate Co., a Japanese company, had owned the world-famous property for less than 10 years, paying top dollar right before rents started dropping. Now, with Rockefeller in bankruptcy, Ackman was competing against real estate investor Sam Zell, as well as a Goldman Sachs-led group that included billionaire David Rockefeller and real estate company Tishman Speyer.
The Goldman group won, but it hardly mattered. The attempt earned Ackman a few mentions in the New York Times and other newspapers—and made him a little money too, because the eventual deal raised the price of his shares in the company that held the buildings' mortgage. He learned that simply getting your name out there could be the victory.
Gotham folded in 2003 after Ackman and his partner ran out of time waiting for a court to allow the merger of two of their largest holdings, a real estate investment trust and a struggling golf course company. Soon after, Ackman started his second hedge fund, Pershing Square.
A few times a year he'd pursue an activist investment. Once he pushed out the leadership of Canadian Pacific Railway, helping to turn one of the worst-run railroads into one of the best over the next five years. In a 2013 interview with Charlie Rose, he said that while the move had made him a lot of money—$2.6 billion—he also saw it as helping the broader economy by improving infrastructure across Canada. Over time, Ackman developed a knack for imparting a sort of noblesse oblige to his trades. 'We like to find investments where our interests are aligned with what's good for America,' he told Businessweek in 2011.
Other times he went short. He'd identify problems at a company, put on wagers that would make money if the stock fell, unveil his findings and wait for shares to tumble. An early high-profile short was the world's biggest bond insurer, MBIA Inc., which he said was more fragile than it appeared, as it insured more and more risky debt. Ackman argued that the company was heading for bankruptcy and that its eventual failure would create risk in the financial system. He hung on even as New York's attorney general at the time, Eliot Spitzer, investigated him for alleged market manipulation. It took years, but the stock of MBIA and other bond insurers he'd bet against eventually plummeted, netting Ackman and his investors $1.2 billion.
But the campaign against Herbalife Ltd. would become one of his highest-profile fumbles. Ackman's $1 billion wager to, as he put it, 'fight evil'—was supposed to take down the nutrition company, a multilevel marketer much like Amway Corp. or Mary Kay Inc. cosmetics. Ackman went after Herbalife on the grounds that it was an illegal pyramid scheme that exploited poor people and immigrants. Over the course of three hours and more than 300 slides at a December 2012 investment conference, he argued his case that the business stayed afloat only because salespeople were forced to buy its unremarkable nutrition shakes, which they often had trouble reselling to actual customers. (Herbalife denied Ackman's claims, though later it paid a fine to the Federal Trade Commission, which alleged that the company 'deceived consumers.')
Billionaire Carl Icahn and fellow hedge fund manager Dan Loeb took the other side of the trade, in a bruising public showdown, with Icahn bashing the younger investor in TV interviews, at one point calling Ackman 'the crybaby in the schoolyard' on CNBC. Icahn and Loeb were soon joined by a handful of other big Wall Street names including George Soros ' family office, pushing Herbalife's stock price higher and higher, causing Ackman more and more pain—what's known in Wall Street parlance as a short squeeze. Loeb posted a note on his bio page visible to traders on Bloomberg Terminals: 'New HLF product: The Herbalife Enema, administered by Uncle Carl.'
After a five-year battle in which he lost his entire investment, Ackman finally gave up and said he was done with shorting stocks in favor of a 'quieter approach.' Now, Pershing Square's business model is considerably more boring: It holds 15 companies, some of which it's owned for years. Ackman is still the final arbiter of investment decisions, but he promoted a chief investment officer as a top deputy. Its holdings are easily recognizable, such as Hilton and Alphabet Inc.
It was during an activist campaign against Chipotle in 2017 when Ackman first started using X (then Twitter) where his approach would become distinctly less quiet. In the midst of his activist push against the fast-casual chain, in which founder and then-CEO Steve Ells left, Ackman posted a photo of himself in line at a Chipotle on his brand-new Twitter account. 'Eating our own cooking @chipotletweets,' he tweeted. By early 2020 he was on Twitter sifting through crowdsourced snippets of ominous information regarding a novel coronavirus in China. That February he bought a type of insurance sold by Wall Street banks that would pay off if corporate bond prices fell, a way to bet on what he saw as the coming disaster for the US and global economies. Ackman spent $27 million on this protection and within three weeks made 100 times his money. He invested some of that gain on a bet that stocks would jump, and soon he added an additional $1 billion to his profit pile.
Meanwhile, Ackman's distrust of media outlets, despite his continued engagement with them, seemed to only grow as he shifted into culture warrior mode. After his anti-DEI campaign against Harvard—in which he amplified plagiarism allegations against the university's president— Business Insider examined the Massachusetts Institute of Technology dissertation of Ackman's wife, Neri Oxman, and said it found unattributed passages and accused her of plagiarism. (Oxman apologized on X for omitting quotation marks in four paragraphs, noting she gave the authors credit elsewhere. In those instances, however, 'I did not place the subject language in quotation marks, which would be the proper approach for crediting the work,' she wrote, adding that she regretted the error.) Apoplectic, Ackman threatened to sue Business Insider 's parent company, Axel Springer SE, and name-checked one of its investors, private equity firm KKR & Co. (He never filed a lawsuit.)
Concluding that journalists wielded too much power, he announced plans to form a think tank to fix media and higher education, poaching an executive from the Manhattan Institute to run it. 'It's really been eye-opening for me to see how stories get covered in mainstream media,' Ackman told podcast host Lex Fridman last year. 'What I do on X is I follow people on multiple sides of an issue, or I post on a topic and I get to hear the other side.'
By early 2024, Ackman was no longer just a financier—his new MAGA-adjacent persona had spilled into the mainstream. He was on the cover of New York magazine, and he described guests at a wedding he attended streaming up to him, requesting selfies and thanking him for speaking out. In recent years he'd overhauled parts of his personal life too, divorcing his wife of more than two decades and marrying Oxman, who has an architectural design company that's made 'decomposing' shoes, silkworm pavilions and a utopian reimagining of New York that film director Francis Ford Coppola used in the creation of his 2 ½-hour sci-fi fantasy flop Megalopolis. Ackman told guests at a dinner party last year that he'd invested $100 million in Oxman's company but that it wasn't nepotism—if it had been, he said, he would have given her only $10 million, according to people familiar with the matter, who asked not to be named discussing private conversations.
Peers could tell Ackman was delighted with all the attention. He recommended reading material on the downfall of American academia to guests at his apartment over wagyu beef prepared by his private chef. He played host in Bridgehampton as part of a more intimate series of private Milken Institute panels held in the Hamptons in August. Back in Cambridge, Massachusetts, at least some Harvard faculty blanched at how this wealthy alum wielded a Wall Street-style pressure campaign to sway their institution's leadership. Ackman framed what he was doing as something else: acting as Mr. Fixit. The same way he'd rehabbed public companies by ousting poor-performing executives and redirecting spending, he was fixing broken American systems.
Part of what Ackman and Buffett had both long understood was the importance of obtaining the ultimate precious resource of money management: permanent capital. The biggest worry for hedge fund managers is that investors might want their money back. When clients ask to exit, managers must sell their holdings to raise cash. If everyone wants to flee at the same time, the business fails. With Buffett's holding company, the only way investors can quit is to sell their shares to someone else. The businesses remain insulated. Ackman has some of that insulation already in his London-listed fund, but he wants it on a bigger scale, with more assets. His performance had improved since 2018, when almost all his capital became permanent—with returns topping 23% a year.
Ackman's multistep plan was to first sell a small stake in Pershing Square to wealthy investors and institutions, raising money to invest in a vehicle he'd create that retail investors in the US could also buy into. (It's difficult and tax-inefficient for US investors to buy into his UK-listed fund.) He concluded that, given his elevated profile, the new fund he was assembling could become one of the largest public offerings of all time, matching the IPO hauls of Alibaba Group Holding Ltd. and Saudi Aramco.
In a presentation announcing his everyday-investor-focused fund, to be called Pershing Square USA (with the stock ticker PSUS), Ackman said he saw his social media following as a valuable asset. There was already a model for this kind of stock-market-linked virality, which was enjoyed by Musk and Roaring Kitty of GameStop Corp. fame, who could move prices of a crypto coin or memestock with a single tweet. 'I have built a relatively large following on Twitter, or X, over time and used it to discuss a number of topics but, historically, for regulatory reasons, have not been able to discuss investment activity,' Ackman said in his presentation.
As he pitched to his X fans and big-money investors last spring, he was simultaneously flirting with the idea of publicly endorsing Trump. Fundraising is considered a risky time for overtly political talk, for fear of turning off potential investors. In private, Ackman's family and certain business associates detected his shifting allegiances and advised him not to go public with his presidential pick, according to a person familiar with their talks. A lawyer from Ackman's philanthropic Pershing Square Foundation had already groused about his escalating X use, according to people familiar with the matter, who requested anonymity to discuss private conversations. (A representative for Pershing Square Capital and the foundation declined to comment.) Says Ackman: 'I love all my good friends, and I respect their views. It's OK to disagree. I don't judge people based on who they vote for.'
By early July—two months after his Omaha appearance—Ackman had completed the first part of his plan. He sold 10% of Pershing Square to major investors for $1 billion, to reach a value of $10 billion. It raised his own net worth to $8 billion in the process, placing him for the first time on Bloomberg's list of the world's 500 wealthiest people. Weeks later, after the assassination attempt on Trump at a rally in Butler, Pennsylvania, Musk formally endorsed him. The next day, Ackman went public with his decision. ' It will take a long-form post to explain my thinking,' he wrote. 'I might even break my own record.' (The tweetstorm on X: 1,800 words.)
Ackman went about raising money for his new $25 billion fund. He sought out some deep-pocketed investors and, when the haul wasn't big enough, went back to the same people who already owned a small piece of Pershing Square, including a few billionaire pals, an Israeli insurer and Iconiq, a wealth manager to some of Silicon Valley's richest people. As part of his appeal, Ackman disclosed in a letter that financier Seth Klarman 's Baupost Group, a venerable hedge fund in Boston, had pledged to buy $150 million in shares. The missive contained so much information about the PSUS share sale that it needed to be made public. The publicity-shy Klarman, a huge Democratic donor, was angry that he'd been outed by Ackman as an investor—and perhaps unhappy to be seen doing business with a big Trump supporter. He pulled his $150 million. (Klarman has repeatedly declined to comment about this transaction.)
By late July, Ackman had only $2 billion of demand for the new fund. On what was supposed to be a routine update call with bankers, he announced he was putting the sale on hold. 'I woke up this morning and had an idea. At Pershing Square we only do great deals—home runs,' he said. 'I'm going to pull the deal.'
The implosion should have been humiliating. Rather than dwell, Ackman had already moved on to his next campaign: getting Trump reelected.
'If I think I have a good idea, you should assume that I put it out there publicly and I share it with the administration'
During Trump's first term, Wall Street was skeptical and sometimes even critical of the president. After the Jan. 6 riot at the US Capitol, Ackman, the most direct of his peers, tweeted at Trump: 'It's time for you to resign and apologize to all Americans.' (He later deleted the post.) This time around, Jeff Bezos, Mark Zuckerberg, Jamie Dimon and most of the billionaire class are toeing the Trump line, hoping to avoid his retribution. The president has already gone after Big Law and Ivy League universities, so what would stop him from retaliating against huge investment banks and private equity firms?
Despite Trump's proclamations of exactly what moves he'd make in a second term, many on Wall Street seem surprised by the economic whipsawing so far: supersize tariffs, a trade war with China, threats directed at the Federal Reserve, a sinking dollar, small-business decimation, convulsing stock and bond markets. Ackman continues offering his advice to Trump on X. At times, White House moves such as the tariff pause or plans designed to cut drug prices wind up closely mirroring Ackman's own suggestions. Asked if he has a direct line to the president, Ackman demurs. 'I've decided the best thing on that front is just not to describe any interactions one way or another with the administration, because I think preserving that confidentiality is just the right thing to do,' he says. 'If I think I have a good idea, you should assume that I put it out there publicly and I share it with the administration.' (A White House spokesperson didn't return a request for comment.)
A day before Berkshire's annual meeting in early May, Ackman was in Omaha for the second year in a row. He and his chief investment officer, Ryan Israel, spoke for more than two hours, taking questions from the audience much as Buffett and his sidekick Charlie Munger did for years before Munger's death in 2023. Most questions were addressed to Ackman, who got personal about both work and life: his winningest moment (meeting Oxman), the key to success (be 'superhealthy'), how to communicate with investors (acknowledge mistakes and take credit for your successes).
The Howard Hughes deal went through shortly after. Within days he was back on X, holding an hourlong 'town hall' about his new gambit. He discussed his plans to build an insurer inside Howard Hughes, explained why he doesn't invest in technology companies and talked about his media consumption habits, including why X is his first read every day. At one point a participant asked him if he was worried about being so outspoken now that he's part of a public company. Would he become more reserved like Buffett, he wanted to know, or keep shouting like Elon? 'The latter,' Ackman said, laughing. — With Alexandre Rajbhandari