In recent presidential elections, a Republican billionaire dominated the cycle’s political conversation. In 2008, the narrative was about the Koch brothers and astroturfing. In 2016, it was focused on Robert Mercer bankrolling the alt right. This year is shaping up to be the Jeff Yass campaign to save TikTok.

The 68-year-old investor is the single biggest political donor this cycle. He built his nearly $30 billion fortune by applying the skills he honed as a professional gambler in the 1970s and ’80s. His backstory sounds like a pitch that’s Rounders meets Moneyball. Yass grew up middle-class in Queens and displayed a preternatural talent for odds-making during weekends at the horse track with his accountant father. In his 20s, Yass formed the nucleus of a professional poker-playing clique. They named their gambling syndicate “RAMJAC” after the fictional conglomerate that owns 19% of the United States in Kurt Vonnegut’s novel Jailbird. Yass’s crew roamed the country scoring big at racetracks, sometimes getting thrown out when the house got wise to their quantitative advantage. After buying a seat on the Philadelphia Stock Exchange, Yass recruited his college friends for his trading outfit, Philadelphia Trading. They used their profits to launch an options trading firm, Susquehanna International Group.

Simply put, Yass’s investing strategy boils down to his ability to smell a mark and take his money. “All of sports betting, all of playing poker, and all of options trading is making sure you’re betting against someone you’re smarter than,” he told a podcast a few years ago. “If you’re not asking yourself, ‘Am I the sucker?’…you get arrogant and you get crushed.” This philosophy made Yass the most successful financier you’ve probably never heard of. He is the richest person in Pennsylvania and a major funder of school choice, his pet issue.

Susquehanna stands out on Wall Street because it doesn’t have outside investors. All of the firm’s money is owned by partners and employees. This freedom gives Yass and his team absolute control over investing strategies, and it enabled Yass to make one of the best plays of the decade.

In 2012, Susquehanna International Group put a few million dollars into TikTok’s Chinese parent, ByteDance, at a time when Wall Street otherwise ignored the fledgling tech company. Today, Susquehanna’s roughly 15% stake in the privately held ByteDance is worth some $40 billion, according to the Financial Times. If ByteDance goes public and achieves Facebook valuation, Susquehanna’s stake would be worth $150 billion. That amounts to a roughly 3,000,000% return.

But Yass’s golden run is in danger. Last month, Joe Biden signed a law that would force ByteDance to sell TikTok to an American company or be banned from the US market. The bill addressed bipartisan concerns that TikTok’s links to the Chinese Communist Party pose a national security threat. Critics accuse China of collecting a vast trove of data on TikTok’s 170 million American users and warn that the Chinese government can manipulate TikTok’s vaunted algorithm to spread misinformation and sow chaos. Some have alleged that the student protests roiling college campuses are being fueled by a favoring of pro-Palestinian content on the social media app.

TikTok has pushed back hard at such allegations. In late 2023, it said it had removed millions of videos related to hateful content in the wake of the October 7 attacks and said in a statement at the time, “Hateful ideologies, like antisemitism, are not and have never been allowed on our platform.”

Still, the platform’s foreign ownership, massive reach, and opaque operations have made it an easy political target. “TikTok is a tool China uses to spread propaganda to Americans, now it’s being used to downplay Hamas terrorism. TikTok needs to be shut down. Now,” Florida’s Republican senator Marco Rubio posted on X in November.

If TikTok is booted from the US, Congress will have played Yass, according to his own stated worldview, for the sucker. Which raises the question: How could the ultimate odds reader fundamentally misjudge the intensity of anti-China sentiment in Washington? It turns out the answer to this very expensive question can be mooted if Yass finds an even bigger sucker to save his TikTok billions: Donald Trump.

On March 1, Yass, along with Club for Growth president David McIntosh, invited the former president to speak at a Club for Growth donor retreat at The Breakers in Palm Beach. The invitation was stunning on multiple levels. Yass is a libertarian Never Trumper who has called Trump the “Democrats’ most valuable player.” Yass told The Wall Street Journal that he tried to stop Trump from running in 2024, recalling that he warned the former president, “You’re gonna lose and be humiliated.” Yass aggressively tried stopping Trump from winning the nomination. According to a Yass representative, Yass donated $10 million to the Club for Growth to run anti-Trump ads on TV in Iowa. Yass directly donated to Vivek Ramaswamy, Chris Christie, Tim Scott, and Ron DeSantis. According to a source, Yass told Christie, “You’re the only one with the balls to stand up and say what needs to be said.”

Then the fates of Trump and Yass intertwined this winter. Just as the former president was shoring up the GOP nomination with a string of decisive primary wins while also incurring mounting legal debts and penalties, the TikTok ban became a rare source of bipartisan agreement. Yass needed someone who could kill the bill. Trump had already proved he could tank legislation: In January, Trump browbeat Republicans until they scuttled a bipartisan immigration bill. Trump needed money—bad.

Gambling is all about understanding your opponent’s weakness. In April, NPR reported that the Trump campaign had nearly $100 million less cash on hand than the Biden campaign. Trump dethroned Republican National Committee chair Ronna McDaniel in part because of weak fundraising. Cash on hand is a major concern for his campaign, but more so for Trump personally. Trump faces massive legal bills and a pending $353 million fine plus interest from New York state. So far, Yass has contributed $46 million to conservative causes and PACs, but nothing to Trump directly. If Trump wins Yass over, it could open the floodgates to a torrent of cash. Not surprisingly, Trump lavished praise on Yass during his Breakers speech, calling him “fantastic.” But Trump’s courtship of Yass went far beyond nice words. A week after Trump met Yass in Palm Beach, Trump made an announcement.

“If you get rid of TikTok, Facebook and Zuckerschmuck will double their business. I don’t want Facebook, who cheated in the last Election, doing better. They are a true Enemy of the People!” Trump posted to Truth Social on March 7.

It was a stunning policy reversal, in no small part because Trump had attempted an earlier TikTok ban himself. In August 2020, Trump released an executive order that directed ByteDance to sell TikTok within 90 days or be banned from the US. “There is credible evidence that leads me to believe that ByteDance…might take action that threatens to impair the national security of the United States,” Trump’s executive order stated. TikTok filed a lawsuit to stave off the ban. (The suit was later dropped after the Biden administration rescinded Trump’s executive order.)

The optics of Trump’s flip-flop were terrible. To many, it looked like Trump had cynically reversed a longtime policy position to impress a major donor. “Trump was Yass’s mark,” a top GOP strategist said. Trump later denied discussing TikTok with Yass at The Breakers in a CNBC interview. But the Yass camp has been lobbying Trumpworld privately. According to a source briefed on the conversations, Yass’s political adviser, Tony Sayegh, has asked Trump senior adviser Jason Miller to convince Trump to defend TikTok. Miller and Sayegh are college friends; they attended George Washington University together. Sayegh is also wired into Trumpworld from his time serving as Treasury Secretary Steven Mnuchin’s spokesman. Both Sayegh and Miller declined to comment.

Trump’s ties to Yass raised even more questions in late March when The New York Times reported that Susquehanna was one of the largest institutional investors in Digital World Acquisition Corporation, the SPAC that merged with Trump’s troubled social media company, Trump Media & Technology Group. From the outside, it looked like Yass’s firm was helping to prop up Trump Media’s stock, of which Trump holds a roughly—and highly theoretical—$5.5 billion stake. Susquehanna released a statement to The New York Times that denied that the Trump Media investment had any political motivation. “Susquehanna is a market maker and has zero economic interest in Trump Media,” the company said.

Another prominent Republican not currently in government who received a political donation from Yass said the financier uses a hands-off approach to push pro-TikTok policy. The Republican said Yass didn’t mention TikTok during their meeting. But afterward, a Yass adviser called the politician and let the boss’s wishes be known. “He said something like, ‘You would do a lot better with him if you change your position on TikTok.’ Or ‘You know, he likes everything about you except your position on TikTok,’” the Republican recalled.

Yass has also poured millions into the Club for Growth. In March, Politico reported that Club for Growth representatives told House Republicans that the influential anti-tax group would punish House members who voted for the TikTok ban. (A Club for Growth rep told Politico that Yass has never asked that “the group take a position or action on his behalf.” The organization did not respond to a request for comment from Vanity Fair.)

Yass’s big bet on saving his TikTok fortune has yet to pay out thus far. But TikTok is preparing a host of legal challenges to the legislation. For now, that means Yass is still at the table. A Yass spokesperson said “there is zero chance that he gives to Trump.” (Yass declined to comment otherwise for this story.) A Trump campaign source said the campaign still hopes Yass gets on board. After all, Yass’s best chance to protect his TikTok winnings is for Trump to become president and overturn the ban.

Want to wager how it turns out?