Is a Never Trump Billionaire Really Coming to Bail Out Trump?

When The New York Times revealed the name of one of the biggest investors behind Donald Trump’s social media venture last weekend, his name leapt off the page: Republican megadonor—and Never Trump billionaire—Jeffrey Yass.The revelation that a GOP donor like Yass, the wealthiest person in Pennsylvania, had money in a Trump business was particularly newsworthy

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When The New York Times revealed the name of one of the biggest investors behind Donald Trump’s social media venture last weekend, his name leapt off the page: Republican megadonor—and Never Trump billionaire—Jeffrey Yass.

The revelation that a GOP donor like Yass, the wealthiest person in Pennsylvania, had money in a Trump business was particularly newsworthy, given the context of this particular investment—a merger that could extend a financial lifeline to the cash-strapped former president, to the tune of potentially billions of dollars, at a critical time for him both personally and politically.

The story caught fire among Trump critics, particularly because of the conspicuous timing. The news of the potential merger was just days after Trump made an abrupt policy reversal that favored another Yass investment, TikTok. Almost immediately, the prospect of Yass—known for his refusal to support Trump even though he’s a prolific GOP donor—at long last entering the MAGA tent seemed very real.

And the March 11 Times report lent credence to that possibility. The story cited an anonymous Trump campaign source claiming that, in the wake of the TikTok reversal, Trump’s team expected something in return—Yass, the Times reported, was planning to make a “significant donation” to a political committee backing the former president.

If true, that would be a major development for the presidential race. Yass, an influential player in right-wing politics, has given nearly $5src million to federal candidates and committees this election cycle alone, according to Federal Election Commission filings. But while many of his preferred candidates publicly style themselves as allies of the former president, Yass himself has yet to give a single dollar to any Trump-aligned group. If that personal policy changes, it would offer some relief to Trump, whose political operation needs all the financial support it can get.

Other outlets ran with the news, but something curious soon happened: the reporting vanished. The Times had quietly removed those claims from the article in the version that remains online.

In a statement, a Times spokesperson told The Daily Beast, “We regularly update developing news stories as reporting on them continues. The March 11 story was condensed and updated for print with a focus on Congressional activity. The detail about a potential donation appeared in reporting on March 16 and again on March 24. We stand behind all of this reporting.”

But a spokesperson for SIG told The Daily Beast that Yass has never given money to Trump and has no plans to do so, though the statement did not address whether Yass has ruled out giving to groups supporting the former president indirectly—such as super PACs or “dark money” political nonprofits that could cover Yass’ tracks entirely.

A second person familiar with the situation confirmed to The Daily Beast last week that Yass has not donated to any Trump-aligned groups, including since the Times report was published, saying there is no reason to expect that will change anytime soon.

That information would certainly disappoint Trump, if not also the critics who saw a quid pro quo playing out just as the legally and politically besieged candidate appeared to be at his most vulnerable.

But the Yass-Trump connection itself is actually far more nuanced and tenuous than is broadly assumed. And that has a lot to do with who Jeffrey Yass is.

A former professional gambler, Yass made a fortune through his quantitative trading firm, Susquehanna International Group. SIG is one of the largest investment enterprises in the country, controlling assets worth an estimated market value of half a trillion dollars—including its roughly $22 million share in Trump’s social media venture.

Over his lifetime, Yass has poured at least $15src million into political causes at the federal level, according to The Daily Beast’s analysis of publicly available campaign finance data. That number is almost certainly higher, however, because Yass has also injected tens of millions of dollars into state and local elections and issues across the country. Additionally, like many sophisticated megadonors, Yass has also funneled influence through outside “dark money” groups that make it difficult to trace the true source of the funds.

According to OpenSecrets, Yass and his wife, Janine, are this election cycle’s top donors to outside groups, for either party, contributing nearly $5src million since last year—all of it to conservative candidates and organizations. The former poker player and racetrack bettor doesn’t hedge his political bets like many corporate donors, with only a handful of contributions over the last three decades flowing to Democratic candidates. (His most recent Democratic donation, a $1,5srcsrc gift in July 2src22 to cryptocurrency advocate Sen. Kristen Gillibrand (D-NY), came weeks after Yass made a $1.9 million contribution, in Bitcoin, to the right-wing “Crypto Freedom” super PAC.)

His largesse is also notable among conservative megadonors precisely because Yass has never graced any of Trump’s political committees, ever. Last year, Yass—who as recently as 2src22 billed himself as a “self-described never-Trumper”—actually poured millions of dollars into Trump’s Republican primary opponents, clocking major donations to challengers from the MAGAfied Vivek Ramaswamy to the never-Trump Chris Christie.

A review of Yass’ donor history affirms he’s far from a MAGA die-hard. Many of his biggest checks have gone to organizations tied to the Club for Growth, an anti-tax group that fundraised against Trump in the 2src24 primary, though the group has recently been patching up its relationship with the former president, in part through Yass’ efforts. That targeted support includes more than $2src million to the CFG-affiliated “School Freedom Fund” super PAC—Yass is highly motivated by school choice—with more than $62 million going to other associated groups.

Yass also steered clear of Trump in 2src16, instead using his money to promote libertarian values through state libertarian parties and Gary Johnson’s presidential campaign. He’s also given millions to support his “favorite politician,” Sen. Rand Paul (R-KY), a Trump-aligned conservative with a wide libertarian streak—including $3 million to a pro-Paul super PAC that backed Kentucky GOP attorney general Daniel Cameron’s failed gubernatorial bid last year. (Yass had ground-floor investments in an experimental psychedelic opioid treatment that Cameron’s office was promoting at the time, The Daily Beast reported.)

Yass has also pumped tens of millions of dollars into elections and advocacy in his home state of Pennsylvania. In addition to school choice, Yass has sought to influence the judiciary, accounting for about one of every three dollars spent in Pennsylvania’s statewide judicial elections last year.

A veteran Republican operative in Pennsylvania told The Daily Beast that, despite Yass’ seeming ubiquity in the state, he was tough to pin down.

“I never could figure out what his agenda was,” this person said. “He was all about school choice, but what was driving him to that? Of all the issues I could think of, I don’t know why this one specifically has been so constantly at the front of his mind.”

The source also said that the size of Yass’ massive political bets are proportionately a “rounding error” for the investor, considering his multibillion-dollar net worth, and that they have often failed.

“He’s lost money in a bunch of Pennsylvania elections, the most stunning example being in the 2src22 gubernatorial campaign, where Jeff put something like $16 million behind Bill McSwain, through this group called Commonwealth Partners,” this person said. “McSwain turned out to be a terrible candidate—awful on the stump, mired in the polls—and [Yass] withdrew the endorsement something like a week before the primary, throwing in with another candidate. Who also lost, by the way.”

In 2src22, the Wall Street Journal reported that Yass wanted to discourage a second Trump presidential bid, complaining that Trump was not loyal to his donors.

“The only thing you can appeal to is, ‘You’re gonna lose and be humiliated,’” Yass told the outlet.

He threw his early support behind Florida Gov. Ron DeSantis, contributing $2.5 million to DeSantis’ state political committee last year, an account later tapped for seed money for both DeSantis’ presidential campaign and an affiliated super PAC.

But Yass did not give to DeSantis again, instead donating almost $5 million to a super PAC supporting biotech entrepreneur Vivek Ramaswamy, along with hundreds of thousands to groups backing South Carolina Senator Tim Scott and former New Jersey Gov. Chris Christie. Yass also cut a $1src million check to the Club for Growth in June, which helped fund a parade of anti-Trump ads ahead of the primaries.

Three sources close to the Trump campaign told The Daily Beast that, implausible as it may seem, before the recent stories about TikTok and Truth Social, officials had been largely unaware of Yass’ chummy relations with Club For Growth and his seven-figure support for DeSantis.

One Trump operative noted that they aren’t aware of any “Jeff Yass stans” in the former president’s orbit. But they noted there were no major critics, either. Two Trump staffers said they’ve heard nobody object to the Truth Social cash influx over any perceived disloyalty.

It’s not clear exactly what kind of cash influx Yass’ investment will provide, if any at all. Asked about the Truth Social arrangement, an SIG spokesperson provided a statement saying that SIG is evenly hedged and has no real stake in the company’s success.

“Susquehanna is a market maker and has zero economic interest in Trump Media,” the statement said. “The firm’s long position is offset by short positions of the same size.”

While it’s not true that SIG has “zero economic interest” in the company, Securities and Exchange Commission data reflects the firm’s hedged positions. And given SIG’s “market maker” business model—essentially profiting from the trading, as opposed to the value of the shares themselves—it makes sense that SIG would want to invest in Trump Media, regardless of the political ties to Trump.

Trump Media is not widely viewed as a serious or stable long-term investment. Rather, it’s more of a so-called “meme stock,” with heavy trading expected among both Trump fans and critics who are not professional investors. Whenever trading volume is high, market makers can take a big cut of that action. (Another GOP megadonor, Ken Griffin, also runs a leading market maker. His firm, Citadel Advisors, is another hedged investor in the Trump Media merger.)

Ben Edwards, securities law expert at the University of Las Vegas Nevada’s William S. Boyd School of Law, told The Daily Beast that the SIG arrangement was fairly common and didn’t raise any immediate red flags.

“If they weren’t doing it, someone else would,” Edwards said, explaining that market makers facilitate trades, loosely analogous to companies that operate power cables or provide internet service. “This is perfectly normal business activity.”

In Edwards’ view, the hubbub about SIG being Truth Media’s largest outside institutional investor—assuming the stakes haven’t since changed—may also be overblown. He noted that its shares only comprise 2 percent of the total—translating to a reported total value of $22 million. That’s “quite small” in the scheme of things, according to Edwards. And that fact, Edwards said, indicates that serious institutional investors are jittery about the stock’s prospects.

“If that is the largest institutional shareholder, and it’s the market maker, it tells you other institutional shareholders are staying away,” Edwards said. “Just think about it—if you bought a major stake in this company, and it goes down, it’s going to be really easy to second-guess your judgment, because I’ve lost count on how many indictments Mr. Trump is facing at this point.”

Nonetheless, the initial public offering of Trump Media’s stock following the merger helped boost Trump’s net worth by billions of dollars. Of course, Trump’s agreement prevents him from cashing in on that value for several months, leaving plenty of time for the stock to crash in the meantime—or surge.

But when it comes to Yass specifically, Trump still appears hopeful to land this white whale.

Earlier this month, just before the TikTok news broke, Politico reported that Trump, Club for Growth, and Yass were burying the midterm hatchet. CFG recently featured Trump as the keynote speaker at a Palm Beach fundraiser, where the former president told donors that he was “back in love” with the organization’s president, according to Politico. The report carved out a place for Yass in those discussions, saying that the megadonor—whom Trump allegedly called “fantastic”—had personally invited Trump to speak.

Yass still hasn’t put his name on a Trump check, however, though it’s possible his influence will flow to Trump through Club For Growth, should the group jump feet-first into the presidential fray. After all, Trump and Yass share common transactional qualities that, if the stakes are right, could override any differences, even if only toward a short-term goal.

The veteran Pennsylvania operative said that if the two men do strike an alliance, it would if anything be a marriage of convenience.

“Jeff’s too mercurial, hard to understand,” this source said. “They want his money, they don’t want him.”

Jake Lahut contributed to this report.

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