You may remember former president Donald Trump once denouncing TikTok, the social video app that includes an estimated 150 million users in the United States and nearly 2 billion globally. Invoking the now-familiar rhetoric about the short-form video app bewitching America’s youth on behalf of our Chinese adversaries, Trump even tried to force TikTok’s sale to a consortium that included Oracle centi-billionaire Larry Ellison, one of his political benefactors. That effort ultimately ran aground in court; meanwhile, TikTok sought to fend off future Trump attacks and takeover bids by beefing up its US operations and promising that it would take measures to ensure that the vast troves of American consumer data the site harvests would remain stateside.

But all that was before Trump met billionaire Philadelphia financier Jeffrey Yass.

A top Republican donor, Yass publicly discouraged Trump from running in the 2024 election. Yass initially supported Florida Governor Ron DeSantis before spreading his bets between Vivek Ramaswamy, Chris Christie, and Tim Scott. But as Trump once again steamrolled his primary competitors, Yass reached out and asked him to speak at a retreat for a powerful right-wing business PAC, the Club for Growth, which has pulled in $61 million in donations from Yass since 2010. The Club for Growth also happens to be employing former Trump adviser Kellyanne Conway to lobby on behalf of TikTok on Capitol Hill.

The retreat seemed to go exactly as planned. Trump praised Yass as “fantastic,” and he emerged as a critic of a TikTok ban. “If you get rid of TikTok, Facebook and Zuckerschmuck will double their business,” Trump posted last week on Truth Social. “I don’t want Facebook, who cheated in the last Election, doing better. They are a true Enemy of the People!”

Yass, meanwhile, is now a certified Trump crony. The 68-year-old is the richest man in Pennsylvania, with an estimated fortune of about $28 billion derived from options trading and venture-capital investments—including a sizable interest in TikTok. Local politicos and activist groups have long faced off against Yass and his bottomless war chest in fights over education, social welfare, and unions. Arielle Klagsbrun, deputy campaign director at the Action Center on Race & the Economy (ACRE), described Yass as a “next generation Koch brother…someone who is rigging the rules to privatize our schools while also not paying his fair share of taxes.”

“His disdain for teachers’ unions, in particular, is profound,” said Klagsbrun, characterizing Yass’s influence as “corporate authoritarianism in our democracy.” ACRE is pressing Pennsylvania elected officials to refuse to take money from Yass in the 2024 cycle.

That may be a tough ask. So far, Yass is the leading Republican donor of the 2024 campaign cycle. He and his wife, Janine, have given more than $46 million to conservative groups and candidates, according to Open Secrets. The couple doled out $56 million in 2022 and $30 million in 2020. Yass didn’t openly support Trump in 2020, instead giving tens of millions of dollars to the Club for Growth and conservative PACs, but he’s expected to line up more directly behind Trump this year.

In 2012, Susquehanna International Group, the trading and investment giant cofounded by Yass, made an early investment in ByteDance, TikTok’s Chinese parent company. That stake now amounts to about 15 percent of the company and is worth an estimated $40 billion. A bit under half of that holding—somewhere in the neighborhood of $18 billion—belongs to Yass personally.

Yass has an enormous financial interest in ensuring that TikTok operates legally in the United States—and that interest could increase, since the House passed legislation this week seeking to compel the sale of the company to US investors under threat of an all-out ban. If that tactic works, then Yass could be well-positioned to assume a larger ownership share. (Former treasury secretary Steve Mnuchin said that he wants to form a group to buy TikTok.) In the meantime, Yass has showered Republicans, right-wing PACs, and big-business groups with millions of dollars in donations.

That’s no small concern, given Yass’s hard-right ideological profile. Trump is likely sidling up to him as a potential Zuckerberg-scale force in social media who closely aligns with the MAGA movement’s policy preferences. Yass ticks many of the boxes expected of the post–Citizens United billionaire class. He’s passionate about “school choice” and less passionate about paying taxes. He’s heavily invested in the charter school movement, denouncing teachers as corrupt, overpaid layabouts. He’s called the Democratic Party an “evil political actor.” He’s on the board of the libertarian Cato Institute and idolizes Milton Friedman, whose 1962 laissez-faire tract Capitalism and Freedom was a core text in Yass’s conversion to conservative economics.

The son of two CPAs, Yass grew up in the Bronx. He was a math major at SUNY Binghamton and a gambler; after college, he tried to make it as a professional poker player in Las Vegas. He and some friends also made hundreds of thousands of dollars implementing a sophisticated betting scheme at race tracks across the country. After one track kicked them out, Yass sued the track owner in federal court. He lost.

Yass eventually landed on Wall Street, where he fell under the tutelage of Izzy Englander, an enormously successful hedge-fund trader. He started trading options on the Philadelphia Stock Exchange and soon invited some of his college poker buddies to join him. They founded Susquehanna, which has grown into a dominant player in options trading, along with various other interests in finance and tech. Poker remains a huge part of Susquehanna’s game theory-driven culture; the company hosts a series of games for employees, and several Susquehanna quants have won bracelets at the World Series of Poker.

Like many fintech moguls, Yass nurses a fierce hostility toward public education, which he attributes to his libertarian mentor Friedman. “He was the guy I respected most,” Yass said at a December 2023 gala for the Yass Prize, which awards millions of dollars to charter schools. “As a gambler, I go with the smartest guy. And he was the smartest guy, I thought.”

Yass believes that students in publicly funded schools are “slaves,” rather than the “customers” they should be. At the 2023 gala, he said that he hopes, decades from now, people will look back in astonishment at the fact that some parents didn’t have access to charter school vouchers. “That’s like looking back and thinking, in 1850 how did you allow slavery? How did something so disgusting exist?”

Trump is the most prominent Republican to come around to Yass’s view on TikTok, but he’s far from the first. Ramaswamy used to call TikTok “digital fentanyl.” But he has had same epiphany that Trump recently experienced. During the summer of 2023, Ramaswamy received millions of dollars in donations from Yass—and sure enough, come September, he launched his own TikTok account, saying he wanted to reach young people. He’s now against banning the app, as are Kentucky Senator Rand Paul and other nominally libertarian recipients of Yass campaign dosh.

Less fortunate fundraiser-lawmakers in the GOP (and the Democratic Party, for that matter) continue to demonize the social-media app as a first-order threat to national security. As a result, the battle around TikTok has been reduced to a Sinophobic moral panic, rather than a complex debate about data sovereignty, free speech, the contested definition of “disinformation,” and Big Tech’s pioneering use of surveillance as a business model. Banning TikTok seems like a crude policy response when America’s tech giants—and its intelligence community—collect vast amounts of consumer data, and when numerous other Chinese apps remain on American consumers’ phones.

As the Biden administration makes progress on antitrust matters, particularly through Lina Khan’s Federal Trade Commission, it’s possible that the White House could steal a march on Congress and engineer the forced sale of a major social-media company. If that’s the case, it might be a victory for the national-security directorate, but it will have cemented American corporations’ tech sovereignty at a cost to American consumers.

Either way, Yass can claim a major financial conquest, but he will have won for the wrong reasons. If the Senate goes along with the House bill, President Biden will have the effective power to mandate a US-backed takeover of the app within 165 days under threat of a permanent stateside ban. Given the platform’s popularity here (and abroad), there’s too much money at stake not to make a deal. That means that Yass may very well emerge from this imbroglio with either a greater stake in TikTok or billions of dollars in profit on what was reportedly a low seven-figure investment.

For now, Yass has the powerful distinction of being the Republicans’ biggest moneyman—at least until another billionaire peels off a few million. (Uline packaging company owners Liz and Dick Uihlein recently affirmed their support for Trump and aren’t far behind.) Having made peace with Trump, Yass gets his turn with the tiller of Republican policy. The former president may have a paper-thin ego, but he’s also easily bought—particularly with a dizzying array of court fines before him. That’s no doubt why Trump is reportedly considering Yass as a potential treasury secretary. For this lifelong gambler, TikTok turned out to be the perfect bet.