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Welcome to Bw Reads, our weekend newsletter featuring one great magazine story from Bloomberg Businessweek. On Thursday, as Elon Musk and Do
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Welcome to Bw Reads, our weekend newsletter featuring one great magazine story from Bloomberg Businessweek. On Thursday, as Elon Musk and Donald Trump were exchanging barbs on their social media platforms, the billionaire Bill Ackman posted on X to say “they should make peace for the benefit of our great country.” That Musk responded “You’re not wrong” is a sign of Ackman’s huge online clout, which Annie Massa and Katherine Burton wrote about last week. You can find the whole story online here. You can also listen to it here.

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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 speaking at the Sohn Investment Conference in New York in 2017. Photographer: Brendan McDermid/Reuters

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.

Keep reading: Bill Ackman Is Tweeting Through It

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