“He’s lost money in a bunch of Pennsylvania elections, the most stunning example being in the 2022 gubernatorial campaign, where Jeff put something like $16 million behind Bill McSwain, through this group called Commonwealth Partners,” this person said. “The only thing you can appeal to is, ‘You’re gonna lose and be humiliated,’” Yass told the outlet. 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. He threw his early support behind Florida Gov. In 2022, 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 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. 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. 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.

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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. “He was all about school choice, but what was driving him to that? “I never could figure out what his agenda was,” this person said. 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.

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“Susquehanna is a market maker and has zero economic interest in Trump Media,” the statement said. 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. Trump Media is not widely viewed as a serious or stable long-term investment. 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. 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.

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