Jeff Yass’s Big School Choice Gamble

Jeff Yass is bankrolling an initiative to change the way we teach children here and across the nation. / Illustration by James Boyle

Jeff Yass surprises me. He wants to talk.

It’s something he almost never does, not to the press, anyway.

He’s been declared the richest man in Pennsylvania, worth perhaps $45 billion, and plenty has been written about how Yass reached that level of wealth, almost all of it with no comment from him. But his operating under the radar goes way back. Yass grew up in Queens, and after going to state college in Binghamton back in the ’70s, he set out for Las Vegas with a couple of buddies to become professional poker players. That didn’t quite work out, but Yass figured out a way to make big money gaming the odds at various racetracks; he started showing up with satchels of cash to place huge bets. And then Yass began chasing a new way to trade on the stock market, soon making a killing in high-volume options trading, a bet on whether stocks will go up or down; he created a company, Susquehanna International Group on City Avenue, that now employs more than 3,000 and works markets all over the world. In many ways, though, Yass has remained a poker player at heart; he uses the game to teach young recruits about odds, about reading other investors, about revealing as little as possible. His company is privately held, mostly by him. And Yass still holds his cards tight.

But his life has gotten larger, and quite complicated. Much of that is his own choosing: He’s gotten involved in politics.­ Yass is now a big giver to candidates, which has made him an easy target — the richest man in Pennsylvania who has contributed more money this election cycle than anyone, mostly to Republicans in this state and nationally, in excess of $70 million. Yass gave $6 million to Texas Governor­ Greg Abbott, who claims it’s the single biggest donation ever to a politician there — and then gave him another $4 million — outdoing all the big-hat oilmen in one fell swoop, and then doing it again. Which has given the press, especially the left-leaning press, an obvious angle: the rich oligarch trying to buy elections for his libertarian goals, putting his millions behind politicians who believe in the sanctity of business and will, especially, lower his taxes. Jeff Yass hates paying taxes.

There’s another complication, not wholly of his choosing. Susquehanna owns 15 percent of ByteDance, the Chinese company behind TikTok, so he has billions of dollars at stake in the forced sale of TikTok that Congress recently passed over the risk that the Chinese government could gain access to and manipulate millions of American TikTok users.

Enter Donald Trump: After a meeting Yass had with Trump in March at the Breakers in Florida — not far from Mar-a-Lago — the past and possibly future president reversed his long-held position against TikTok to suddenly go all in on it, which has given the media another angle of attack: that Yass, a former Never Trumper, perhaps had promised Trump what he so desperately needed — money — in order to save his interest in ByteDance. Which would make him an oligarch and a hypocrite to boot. And now there is even noise that Trump is considering Yass for Treasury Secretary, if Trump wins. (Yass denies that he’s planning on giving any money to Trump.)

I email Yass. I don’t mention any of the above. Instead, I tell him I want to talk to him about, of all things, education. Because this is the most important thing on his plate, Yass has claimed: He wants to radically reform the way we teach children in America.

I do want to talk to Yass about education — to suss out what that’s all about — but my interest in him is really a little broader than that, even broader than any of the business above. I want to see if I can understand what he really wants, this very private guy who now finds himself with demonstrations at Susquehanna, roasted in Stephen Colbert’s monologue, the subject of long investigative pieces attacking his aggressive involvement in politics. Yass has become the new poster boy for greed and power in America. So let’s talk education — that, too, has him in hot water. He’s a staunch proponent of school choice, and on first blush the question is why, given that the next 10 (or 50) generations of Yasses will be able to afford the private schools of their choice.

To my surprise, Jeff Yass summons me to City Avenue for a conversation.

One June morning, here he is: bald, tall, trim, a button-down shirt and khakis, rimless glasses, as if there is no reason at 66 to come forward into style and fashion beyond 1980; the informality he created here at Susquehanna, his glass-and-steel emporium, looks like old-school casual Fridays. We sit in a small conference room with his media guy and an in-house researcher, who’s got a raft of papers on the sorry state of education in this country.

Fifteen years ago, I wanted to write about Yass and Susquehanna for this magazine. We had a meeting at Chops on City Avenue; I had my editor and publisher in tow, he had his people. One of them said that Yass was worried about security, about my revealing where he lived — it seemed like a very important sticking point. I agreed not to reveal his address. I don’t remember anything else about the meeting except that Yass himself did not say a word, letting his subordinates speak instead. It was strange, to say the least, though I would come to realize it was really about leverage, about making me the mark. If he said a word, he was giving me something, and Yass wanted to keep himself and his business under the radar as I revealed myself. I wrote the piece without him. When it came out, he left our publisher a message: “I liked it. Goodbye!”

Which I thought was pretty funny. I hadn’t done him dirty, he was saying — such as revealing exactly where he lives — though that didn’t change anything. He still didn’t want a conversation; he was gone without ever arriving.

Now, though, Yass is as pleasant as an economics professor, yet when he starts talking about education — about school choice — he sounds more like a moral crusader on how our public schools are failing children:

“There is no possible way a govern­ment monopoly could be a better approach to schools than market competition, particularly­ for poor children. It’s a civil rights issue.”

In the way that children of color are trapped in bad schools in Philadelphia and other cities, especially — once, we wouldn’t let them in. Now, he says, we won’t let them out.

Yass believes getting rid of what he considers deadwood teachers and administrators and ending the overpayment of those who stay (and their huge union-driven benefit packages) is paramount. Public schools are set up, he believes, for the people who run them, not for children.

Yass wants the money we spend on education to follow the children. In Philadelphia, that’s about $26,000 a year, he says, on each student in a public (non-charter) school; Yass would divide that in half, with $13,000 at a family’s disposal to spend on a school of their choice — private or parochial or charter or public. The rest, that remaining $13,000 per year, would be invested into an account for the student that would grow, untouched, until she was 18, a high school graduate, at which point $200,000 or so would be sitting there for her to use on college or jump-start her adulthood. With that, everything would change for Philadelphia’s children, especially, Yass believes, the poorest. As to whether $13,000 is enough to pay for a school of choice, Yass’s researcher chimes in that Roman Catholic High School in Philly costs $10,425 a year; if you leave the bloated public system behind, why yes, it’s certainly enough.

Yass delivers this plan as if the sense of it is obvious; I ask if there’s a growing political will to make it happen. “Yes,” he says — again, without doubt.

“You can’t measure how happy kids are,” Yass goes on. “And that should be more of the focus, how happy they are. Charters are places where they can have pride and not get beaten up. It’s so cruel to see how miserable kids are and for society not to care.”

As he talks, I’m trying to match this guy with the one I learned about 15 years ago. Normally, on the highest level of politics or business, there’s an edge that can’t be hidden. In business, Yass is driven. But with education, he doesn’t seem to be pushing for something so much as utterly assured that he’s right.

Consider, first, the shrewdness and aggression of Yass the businessman. Susquehanna has made a killing in options trading, which requires high-volume bets at warp speed on stocks going up or down. Suppose Microsoft is selling for $130 a share; for a very small percentage of $130, you can buy an option to buy Microsoft at, say, $140 — that’s known as a “call,” and you’re betting that the stock will go up. If it does go up to, say, $150 before your option expires, you can exercise it, buy the stock at $140, and — if you so desire — sell it at $150. If Microsoft doesn’t go up, you let the option expire, and all you’ve lost is the price of the option, the “premium.” Conversely, if you think Microsoft is going down, you can purchase the right to sell the stock at $120 — that’s a “put.” If the stock falls to $110, you can buy it at that market price and exercise your right to sell it at $120. Here’s the beauty of options: If your analysis is right, you can make almost as much money as you would have by buying the stock conventionally. If you’re wrong, all you lose is your premium.

Milton Friedman, famously Ronald Reagan’s favorite economist, gave Yass the philosophical backing to become a financier: When Yass read Friedman’s Capitalism and Freedom he was in his late 20s; a few years earlier, in college, he’d flirted with socialism. But reading Friedman changed his thinking, teaching him about not just free markets’ legitimacy but their importance, how much we need them: “All progress is based on one person lending money to another,” Yass tells me.

But Yass had some early doubts about his own methods. He made several million dollars in one day in October 1987 off the market crash, and he took a deep foray into program trading, an early use of algorithms that was highly criticized for creating too much market volatility. Yass had heard that Friedman, who was then teaching at Stanford and whom he’d never met, would field two questions a day, from anyone, if he found them interesting. This was Yass’s: “Is program trading moral?” A few days later, he was at the Philadelphia Stock Exchange when he heard an announcement: Jeff Yass, Milton Friedman is calling. He wants to speak to you. “He called me collect,” Yass says, laughing. “He wasn’t going to spend the five dollars.

“He said, I’m not an expert. I assured him that he was. Are you violating any laws? No. Are you obeying the rules? Yes. Then if you’re making money and getting prices in line, since futures are out of line with stocks, okay, then it’s full steam ahead.”

It turned out to be a very lucrative phone call.

The point, though, is that there’s a bit of philosophical thinking behind Yass’s business, even a moral stance on the importance of helping money flow to nascent businesses. Of course, this is exactly the sort of thing that gets the press up in arms: It’s a morality that also happens to justify getting filthy rich and, especially, what he’s now doing with that money: trying to become a major player in politics.

And trying to remake education by taking on the monopoly of our public schools, which, it turns out, began for Yass with Milton Friedman too.

School freedom would help the world. I’ve never been more sure about any bet I’ve ever made. Because I know the other side doesn’t care about educating children — they only care about protecting their patronage and political power.” — Jeff Yass

For two decades, Yass was a board member of the Cato Institute, a libertarian think tank that pushes for limited government both here and in foreign affairs, the drastic lowering of taxes, and privatization of many government agencies. At a Cato event in the ’90s, he had a different sort of question for attendee Milton Friedman:

“‘If you had a lot of philanthropic money, what would you do with it?’ And Friedman said, ‘I would fight for school choice. That’s the fundamental problem with the country. Nothing is more valuable than school choice.’ So as a gambler, I was like, well, I got to ask the guy who has the best opinion. I want to bet with him. So it certainly made sense to me. … [It’s] pretty obvious that nothing could impact society as much as school choice.”

Which is a window into Yass’s way of thinking: He drills down into the most rational viewpoint held by the smartest people — ­of course, he’s the one deciding what’s most rational and who’s the smartest — ­and then runs with it. He trusts his own pursuit with impunity, and now I can feel how his preternatural obsession with winning — the poker player who made his bet on the markets and won big — is connected to how he thinks the world should work, when it comes to, say, philanthropy, meaning his big school choice initiative. “This is the biggest bet I’ve ever made,” Yass tells me, his voice rising now. “That school freedom would help the world. I’ve never been more sure about any bet I’ve ever made. Because I know the other side doesn’t care about educating children — they only care about protecting their patronage and political power.”

Jeff Yass at the 2013 World Series of Poker in Paradise, Nevada / Photograph by Eddie Malluk

What we need, what we must have, in Yass’s view, is a marketplace of education, competition that will make our schools so much better, and will also, Yass believes, historically reduce poverty in a city like Philadelphia.­ It is, indeed, a huge bet.

But perhaps something else will be wiped out as well: our public schools. Jeff Yass has strong opinions about that too.

“As students flee [to schools of their choice], those government schools would have to shut down,” he says, trotting out his favored term for public schools. “And that’s a good thing. If a school cannot fix itself, if it does not adequately educate its children, if it shortchanges the families it is supposed to serve, it doesn’t deserve to be open.”

At the same time, Yass says, “no money will leave the system. The amount of government spending on education remains the same. The difference will be that the money remains with the child and goes for their education. It just doesn’t go to the big, wasteful bureaucracy anymore. It goes to schools that properly educate students.”

So there it is, Yass’s answer to the central fear of universal school choice, that it would destroy public schools. That’s not a problem at all, he says. Bring it on. Sayonara.

None of this, surprisingly, makes him sound like a crank. What it does, as he explains himself, is make him the utterly self-assured guy I’m sitting with on City Avenue. Because Jeff Yass has absolutely no doubt that he is right.

Not long after that meeting at the Cato Institute where Milton Friedman championed school choice, Yass started working on it. David Hardy, now president of Girard College, a private boarding school in Philadelphia for low-income, single-parent children, would run into Yass at cocktail parties in the Philly suburbs; both men sent their children to the private Haverford School. (Yass has four grown kids, two of whom now work at Susquehanna.) Hardy, a teacher and administrator, worked in a school in a rough neighborhood in North Philly, so he was the perfect guy for Yass to bounce his thinking off of.

I ask David Hardy if Yass mentioned Milton Friedman.

Hardy laughs. “Oh, yes. And I’ll tell you, when he’s on to something, he’s a very convincing guy.”

Hardy gave Janine Yass, Jeff’s wife, a tour of Community Academy of Philadelphia, the school where he worked, which was eye-opening for her. In 2007, the Yasses and Hardy would open Boys’ Latin, a charter high school. Ninety-four percent of students are African American, and many of them struggled badly in public school. Boys’ Latin provides a classical education; it’s grown to 770 students, and according to recent Philadelphia School District stats, about half of them will go on to college. (That percentage went down considerably during the COVID pandemic and hasn’t recovered.)

I wonder how directly involved with Boys’ Latin Yass was.

“Do you know anything about Jeff Yass getting off the trading floor?” Hardy asks, laughing. “He doesn’t.” But in the case of Boys’ Latin, Yass not only funded it but once it got rolling, he came to lunches with parents, to school events, to graduations.

I can see where Hardy’s going, but I ask anyway: “Why?”

“Because he loves children,” Hardy says.

Yass wasn’t going to get what he wanted one school at a time, however. To scale up, to foment the revolution in education he was looking for, he would have to dive into politics.

In recent election cycles, Yass, who calls himself a libertarian, has supported almost all Republicans; early on, he was more ecumenical: Poor Black voters tend to elect Democrats, so why not push them on the obvious problems of education? Wouldn’t they listen? Back in ’07, he got a meeting with Barack Obama, as he was running for president, at Union Station in Washington, DC. “He was pleasant,” Yass says, “and he asked the right questions. His administration would be open to school choice.” But then Obama got advised, Yass says, that he couldn’t go that way, and became, in Yass’s view, just another Democrat caving in to a big donor he couldn’t ignore: teachers unions. State Senator Anthony Williams remains an exception, a Democrat from West Philly whom Yass has supported big-time since 2010, when Williams ran for governor. Williams had been interested in school choice since the mid-’90s, as he saw how troubled the system was and heard stories from his mother, a Philadelphia schools administrator.

State Senator Anthony Williams speaking at the Pennsylvania Democratic Party’s Independence Dinner at the Pennsylvania Convention Center in October 2022 / Photograph by ZUMA Press, Inc./Alamy Stock Photo

“I thought it really did take guts for a Black politician to support school choice,” Yass says of Williams, then smiles wryly. “Many issues we don’t agree on — Tony’s not a free-market guy. But that’s not important compared to school choice. It was a long shot, but if he won the governor’s race, it would have been transformational.”­ The $5 million Yass (along with fellow Susquehanna­ founders) gave to Williams’s campaign in 2010 set a record, stunning political observers. Who were these guys? And what did they want?

Williams lost that race, of course, just as he lost for mayor against Jim Kenney in 2015, when, Yass claims, a majority of Williams’s­ funding came from a PAC supported by Yass.

Yass made only one demand of Williams early on: that he stay the course on school choice as a viable alternative. “The one thing he said I couldn’t do,” Williams says, “was change my position. To cave in.” I ask Williams about that $13,000 Yass proposes to put away for every Philadelphia schoolchild each year until graduation, whether that makes sense to him; Williams dodges a direct answer but makes it clear he isn’t as pessimistic as Yass on the viability of public schools, saying that what they require to succeed is strong support from parents. School choice, for Williams, is an option, not the driver. “He has his approach,” the senator says. “And I have mine.”

The past few years, Yass’s political giving has increased, in Pennsylvania and beyond, to candidates who support school choice, with decidedly mixed success and some head-scratching decisions: Bill McSwain was an absurdly weak candidate for governor in 2022 whom Yass was instrumental in funding with $12.9 million through a series of PACs — “the dumbest thing I’ve ever seen,” says one longtime observer of state politics. Yass tried to get McSwain to quit right before the Republican primary, fearing a split vote that would anoint election denier Doug Mastriano as Josh Shapiro’s­ opponent, which, of course, was exactly what happened. (Shapiro himself made a firm nod toward supporting vouchers for school choice, but then backed away when push came to shove with the state Democratic caucus over his latest budget, which had Yass writing an opinion piece for the Wall Street Journal demanding that Shapiro live up to what he said he believes in.)

Yass has had some success in his political­ giving, as he keeps his focus on transforming education. Also in 2022, a Yass-backed PAC funded winning primary opponents of state House Appropriations chair Stan Saylor and State Senator Pat Browne. Saylor, it turned out, who is highly conservative, had made the fundamental mistake — at least per Yass’s agenda — of getting a little too chummy with public school funding by backing PASA, a superintendents’ association. Moreover, bouncing Saylor and replacing him with a backbencher made a broad, Trump-style point: Toe the line or you may find yourself in the fight of your life. “It’s all or none,” Saylor says. “And I was one of those that, you know, wasn’t all.”

Yass has begun aggressively bankrolling harsh attack ads, going much more harsh than back in the day when he started with Williams and wouldn’t go negative. Yass dollars were behind 11th-hour ads against Helen Gym’s mayoral run that highlighted her husband’s ties to a pharmaceutical company; he bankrolled another attack, on the Working Families Party. Though the possibility of getting anointed by Yass money certainly remains attractive: Matt Wolfe, a Republican city ward leader, reached out to Yass’s team for support for his City Council run in 2019. Alas — and you can hear in his voice a wan sense of if only, given the size of Jeff Yass’s wallet: “They didn’t call back.”

He’s spending money toward wrecking our public school system because he wants everything privatized and profit-driven. Public schools are neither.” — Councilwoman Kendra Brooks

Pressing deeper into politics, Yass says, has all been in the name of giving children, especially poor children, a better education.

There are plenty of stakeholders who don’t see it that way, who rail against his big-money aggression. Councilwoman Kendra Brooks, for one, who won reelection last year despite those Yass-funded ads attacking her Working Families Party for not voting to ban supervised drug injection sites and wanting to defund the police, needs no urging to launch into what Jeff Yass is up to:

“I don’t think he really gives a damn about education policy for the families and children in my community. I think that it’s an excuse to avoid paying taxes. He isn’t really concerned about public education and about putting money directly into supporting schools. He just started his own scholarship fund, and he wants to fund private schools. But if he really cares about Philadelphia children and Philadelphia public schools, he can pour that money directly into schools.

“He’s spending money toward wrecking our public school system because he wants everything privatized and profit-driven. Public schools are neither.”

Brooks doesn’t know Yass. I ask her what she would say to him if they met.

“I really would like to know the why,” she says. Why his focus is on Black and brown children and why he thinks he knows best what they need. “Why does it have to be grounded in pulling these children out of their communities and transforming them into something different?” These are not unique criticisms.

There also seems to be a sort of willy-nilly gamesmanship to some of Yass’s political donations. In mid-June, I call Matt Brouillette, who serves as Yass’s coordinator for much of his political giving in Pennsylvania, and he tells me that they are “having a conversation next week about the row offices” — attorney general, auditor general, and treasurer — to see whom they want in, or out. It feels casual, whom they will pick off, as if — as with Saylor, as with Brooks’s complaint about Yass roaring into the inner city as if he owns the joint — that one overriding consideration (school choice!) gives him license to play this game any way he pleases.

Which doesn’t necessarily undermine Jeff Yass’s commitment to his agenda, but it brings in something else. A longtime friend of Yass’s, who worked with him in the early days of Susquehanna and admires him, has heard people claim that Yass, based on what they’re reading about him in the press lately, is a bad guy; the friend disagrees. “He’s a good guy,” he tells them, someone who operates out of core beliefs. But as I press him further on what Yass is after, he adds something in little more than a whisper — as if he doesn’t want to go there — on what also motivates his friend, and there it is, so obvious it can’t be ignored: “Power.”

The power to upset the apple cart, to blow things up, to have his say. Along the way, there have been serious growing pains: The reports on charter schools’ success, for example, are decidedly mixed. And Arizona, which has served as the model for voucher programs nationwide, has had to cut hundreds of millions from critical programs as the expense of paying private schoolers’ tuition has skyrocketed beyond projections.

Meanwhile, Yass keeps pushing. Three years ago, he and Janine established the Yass Prize to honor and help what they call “educational entrepreneurs,” meaning schools that offer something new in, especially, struggling communities. Last year, Valiant Cross Academy in Montgomery, Alabama, won $1 million for creating a disciplined culture with a Christian emphasis for about 200 students; in 2022, 100 percent of the senior class graduated, many the first in their families to do so.

When I ask if he’s still working with Tony Williams, Yass smiles and says he was in the office last week, sitting right where I am now.

They strategized over PASS, the state program that would provide vouchers to students in the lowest-performing public schools. “I needed to get Yass’s feedback,” Williams says of the program’s political viability, “because he is more in contact with Republicans than I am.”

It’s wrong to think that Yass’s financial largesse is all about school choice. As Bloomberg News recently summed up:

He and his partners fund a vast network of political donor groups and libertarian, free-market think tanks, including the Cato Institute Inc., where Yass sat on the board for decades and to which the Susquehanna Foundation gave $6 million in 2021 through 2022.

And this from ProPublica, which published a deep dive on Yass’s aggressive stance on reducing his taxes two years ago:

In recent years he has given $32 million to the anti-tax stalwart Club for Growth. This money paid for TV ads attacking candidates who were seen as wobbly on Friedman’s tax-cuts-anytime-anywhere philosophy.

Or this from the Washington Spectator last year:

In 2018 and 2020, Club for Growth “spent $20m supporting 42 rightwing lawmakers who voted to invalidate the Biden victory,” according to the Guardian. CFG’s “Patriot” list includes some of the most vocal election deniers in Congress, like Reps. Matt Gaetz, Andy Biggs, and Lauren Boebert.

(Yass has had a long involvement with the Club for Growth, which raises money for fiscally conservative candidates, ones who, as Politico once put it, adhere to a “free-market,­ free-trade, anti-regulation agenda.”)

T­here’s a lot more where that came from; once Yass became, in the last couple of years especially, such a big funder of politicians, long investigative pieces tracking his money followed.

An important distinction has to be made, though; it depends on how we define “political giving.” His bankrolling of PACs whose role is giving to candidates is one thing, and it does invariably seem to start with candidates’ views on school choice, while his Cato and Club for Growth roles, in particular, pushing into tax cuts and health care and deregulation, conservative and libertarian issues also near and dear to him. Which, in turn, allows the left to put a neat, Betsy DeVos-style bow on Yass’s interest in education. To hammer him for the privilege inherent in his wealth. To paint him as an oligarch and a “Trump megadonor,” as MSNBC recently pegged him (he’s not). To start with the certainty that Jeff Yass is a very rich man who wants, more than anything, to ramp up that privilege.

Including through education reform, and when I talk to Yass about this — when I ask him about the press he’s now getting — it’s the only time he seems angry: “If a billionaire wants to do it, he must be up to something nefarious. That is the mega lie.”

Though Yass hasn’t helped himself lately in the court of public opinion with the dance he’s doing with Trump.

As recently as 2022, Yass was, he claimed, a Never Trumper, which makes obvious sense: Yass, hyper-rational, every move he makes based on knowing what’s real and true and most likely to happen, compared to … whatever Trump is. It’s hard to imagine them in the same room.

Yass told the Wall Street Journal in 2022 that he was considering how to convince Trump not to run this year: “It’s not like you can influence him at all. The only thing you can appeal to is, ‘You’re gonna lose and be humiliated.’” Yass tried to stop him directly, giving the Club for Growth $10 million to run TV ads before the Republican primary in Iowa; he donated to Vivek Ramaswamy, Chris Christie, Tim Scott, and Ron DeSantis. According to Vanity Fair, Yass told Christie, “You’re the only one with the balls to stand up and say what needs to be said.”

Though that didn’t stop Yass from calling Trump when he wanted help supporting candidates across Texas this year. “I needed his support for school choice,” Yass tells me. “I told him 15 candidates were great, and Trump said, ‘Let me see if they’re okay.’”

I wonder why Trump would be so interested in helping Yass out in Texas.

“Because he believes in school choice,” Yass says. “He knows how important it is. It wasn’t much of an ask.”

Trump ended up supporting, Yass says, 13 of the 15 candidates.

Meanwhile, Yass had a growing problem, in owning 15 percent of ByteDance, the Chinese company that owns TikTok (court documents in a civil case had revealed that Susquehanna was instrumental in creating ByteDance). Congress was pushing through that bill forcing the sale of TikTok, potentially putting tens of billions at risk for Susquehanna.

This past winter, the Club for Growth’s president invited Trump to the Breakers in Palm Beach to speak on March 1st to a contingent of club donors. Jeff Yass was there.

He spoke briefly with Trump before the former president addressed the donors. Yass says he thanked him for his help in the Texas elections and introduced Janine to Trump, telling him she is a big school choice advocate.

“I love school choice!” the former president gushed.

During his speech, Trump said to the assembled Club for Growth faithful, “We’ve had our fights, and now we’re back in love!” And he gave a shout-out to Janine: “We have Janine Yass here! She’s great on school choice!” Janine momentarily blanched, Yass says, to be singled out — she’s not a Trump supporter either.

A few days later, President Biden announced he would sign the bill forcing the sale of TikTok. Meanwhile, Trump flip-flopped his position — through an executive order in 2020, he had directed ByteDance to sell TikTok within 90 days or face a ban from this country; the order was delayed by litigation. Trump posted on Truth Social on March 7th: “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!”

The press had a field day: The fix was in. Yass finds this highly annoying: “The coincidence that I meet with him, and a couple days later he flipped — it’s settled science in the press that he did it for me. He didn’t.”

Which leaves an obvious question hanging: Why did Yass come to see Trump at the Club for Growth in the first place? So that he could say the magic words “school choice” in his ear? Both Yass and Trump have said that’s all they talked about. Briefly.

Back in early March, Trump was desperate for money to fund his campaign. And Yass was desperate for a turn on TikTok — and he had been working on Trump behind the scenes. According to Vanity Fair, Yass’s political adviser, Tony Sayegh, had requested that Trump senior adviser Jason Miller persuade Trump to reverse his TikTok stance. (Sayegh and Miller have been friends since college at George Washington.)

I don’t doubt that school choice was the topic at the Breakers, as Yass introduced Janine to Trump. But Yass was well aware, given his call for help in those Texas elections, of where Trump stood on that issue. And Yass acknowledged to me that he had taken the opportunity, a few years ago, to plead his case on the issue most important to him when Rand Paul invited him along for a round of golf with Trump.

Now, “school choice” was simply Yass’s way of saying hello. Or more pointedly, saying to Trump, face to face, Here I am. Yass wanted it both ways, I believe: to stay at a remove from Trump as he brought him in.

Yass wasn’t planning on giving him money. At least not directly. He didn’t have to — Trump came through for him. As one political operative put it, in coming out against the TikTok ban, Trump was Yass’s mark. Though it backfired when Trump leaped too soon.

The wheel keeps spinning. Yass would go on to pen an op-ed for the Wall Street Journal, lauding how much better on school choice Trump would be than Biden. Which doesn’t tell us that Yass has taken a dive into the Trump orbit — it’s still awfully hard, for example, to imagine Jeff Yass playing the obsequious game of Treasury Secretary under Trump. But this dance with Trump unfolding in the home stretch of an election where the future of democracy may hang in the balance is, to say the least, unsettling.

The way Jeff Yass operates — the bottom line of who he is and the answer to my question of what he really wants — is all of a piece, it turns out.

Consider two final examples.

The first gives all we need to know to understand how Yass got rich, though it predates his getting into options trading: One day back in the early ’80s, Yass and a few friends went to Sportsman’s Park on the outskirts of Chicago, a horse-racing track first built by Al Capone to race dogs. They carried $60,000 in hundred-dollar bills, rolled up in duffel bags, and made a “Super Bet,” which involves picking the winning order of three consecutive races. Yass had figured out how to game the system: Once the pot got large enough, if you bet enough money and essentially bought all the winning combinations, the odds fell dramatically your way.

That day, Yass and friends left Sportsman’s Park with $600,000.

They had found the flaw, the hole, the mathematical angle that won. (Though racetracks soon caught on to their scheme and banned Yass; moreover, carrying around satchels of hundreds was a little risky.) That’s what he brought to Wall Street: a way to beat the system. Winning was the real point; getting rich was a bonus. This is who he was, and what he would chase because he was driven to do it. And he found a way to think about what he does, about progress and capitalism, and how his expertise — options trading — was part of creating markets. Markets mean opportunity. Markets mean things get invented and made and society progresses, which is a moral good. If that sounds like a high-level rationalization to you, it’s really quite the opposite for Jeff Yass. He is a believer.

The second example is about transforming education. In Texas, Yass not only donated $10 million to Governor Abbott’s war chest but supported, per Abbott’s direction, those 15 candidates across the state running this year for various offices. Observers in Texas were mystified. The following is part of an editorial in the Examiner, a small newspaper in Southeast Texas:

We asked why West Texas billionaires were spending so much on this campaign. We answered it clearly: They want control of the Texas House, and [state House Speaker Dade] Phelan won’t give it to them. Now, we ask what in the world the richest man in Pennsylvania wants with this House seat from Southeast Texas? What does he want with control of the Texas budget, our surplus funds and natural resources?

The candidate Yass supported against Phelan, David Covey, is a far-right Christian conservative from Orange County. Covey calls himself a “conservative warrior” and, according to the Houston Chronicle, pledged to hit the ground running on immigration in the legislature by filing a bill “to declare an invasion of our state and authorize [the Department of Public Safety] to repel invaders at the border.” He also promised to bring a vote that would allow Texans to secede from the U.S. Covey’s angle on school choice is homeschooling.

Greg Abbott at the Texas Motor Speedway while running for governor of Texas in 2014 / Photograph by Tom Pennington/Stringer/Getty Images

When I meet with Yass, I read the editorial from Texas to him and ask about vetting candidates he’ll support. “Governor Abbott said to me,” Yass says, “that the Texas Speaker is not our friend, this other guy would be. It’s all about school choice.”

I tell him about some of Covey’s extreme beliefs.

Yass claims that he was unaware of that; Governor Abbott, he says, told him Covey was a sane human being, and if there were a really bad guy who was in favor of school choice, Yass says he wouldn’t support him.

Later, I press Yass on that: What of conservative candidates he supports who would try to cut spending on programs that help schoolchildren — Head Start-type programs, say, or school lunch programs — in the name of cutting taxes? Does that concern him at all?

“No, frankly,” Yass says. “Because the school choice issue is so much bigger than anything else that I don’t really consider those things.”

Perhaps whether Covey is a bad guy is debatable, but Yass not knowing exactly whom he supports — or considering the fallout from what policies they’ll pursue — is chilling. (In the end, Covey lost. Barely.)

Yass says that what he wants more than anything in America is a much better education system, and I believe we can give him this: He does want to reform education. We also desperately need to have an open debate on the state of our schools, our urban schools especially, a debate Yass says he would welcome. But to many people, it looks like he leaped from debate to certainty long ago, and that he is dangerously gaming our politics with all the money he is throwing around in the name of education. That criticism doesn’t matter, not to Yass. Because he believes he is right.

Because he is utterly certain that he knows the answer:

“If the money in education follows the children” — instead of flowing to teachers and administrators, to the lousy government system — “it will bring them out of poverty. There will literally be a historic reduction in poverty in America.”

(One counter-argument is that in public­ education, the money already does follow the children, but because the money­ is tied to property taxes, more of it follows the rich kids.)

To Yass the money spent on public schools is utterly wasted. And it is his nature — or as he prefers to think of it, it’s a moral necessity — to pursue education reform for all it’s worth.

We should expect Jeff Yass to double down, for his political activism to get bolder and even more aggressive. He knows how much America’s schoolchildren need help — so there is no other way for him to go.

Published as “Jeff Yass’s Big School Choice Gamble” in the September 2024 issue of Philadelphia magazine.