Hey, Teddy Schleifer here.

Welcome back to The Stratosphere and thanks as always for following our work here at Puck.

In today’s piece, my inside-the-room reporting on the blossoming relationship between Peter Thiel and J.D. Vance, and how that is paying dividends for the Ohio Republican Senate hopeful, who just won a Trump endorsement and another check from his billionaire benefactor. I also endeavor to answer an essential question circulating in Republican big-money politics: Does Thiel want to be the next Sheldon Adelson, or does he really just care about his two protégés? My answer, below the fold.

But first, two nuggets from last week’s F.E.C. filings:

• This weekend I took note of a very mysterious $14 million donation. I’ve covered money in politics for a while now, but I had never before seen a crypto trust LLC listed as a donor to a super PAC. But that was what Protect Our Future, a new anti-pandemic super PAC spending big in Democratic primaries this year, told the F.E.C. over the weekend—that it had received a whopping sum from “Prime Trust LLC,” without disclosing any additional information, as required. After weekend inquiries from us and other outlets, the PAC admitted the screw-up and disclosed the actual donors. The reason I care about the super PAC to begin with is because Protect Our Future is the main election group of crypto king Sam Bankman-Fried, whose effective-altruist political crusades have turned heads in Democratic circles. S.B.F. told me a while back that he had spent $20 million or so on pandemic-related efforts, including this group. $13 million of the $14 million raised by the super PAC, it turns out, came from one person—him.

• A few other donations that caught my eye: Democratic mega-donor Reid Hoffman put a half-million into a Republican super PAC on behalf of LGBT conservatives; Oracle founder Larry Ellison dropped $1 million into a super PAC behind former Mike Pompeo spokeswoman Morgan Ortagus in Tennessee; and Sequoia’s Doug Leone and his wife, Patti, gave hundreds of thousands to committees aligned with Kevin McCarthy and Mitch McConnell.

The second theory, which I often hear from Thiel’s friends, is that his interest in kingmaking has been somewhat exaggerated—that P.T., as he is known by his inner circle, has a narrow, mostly personal interest in the success of his two protégés, J.D. Vance and Blake Masters, whose U.S. Senate campaigns he has sponsored in Ohio and Arizona to the tune of $10 million each.

The more complicated reality, however, is that Thiel has seemed to oscillate between the two narratives. He has surrounded himself with professional Republican strategists who are very much trying to keep him engaged: On some days Thiel is a political obsessive with probing questions about individual districts, but he also expresses the desire to focus on other passions, from Bitcoin to his new family. Which narrative bears out depends in part on how Vance fares two weeks from today, when Ohio Republicans decide on their nominee. And that’s why every Republican who wants Thiel to remain active in G.O.P. politics should be rooting hard for Vance, if solely to keep Thiel’s appetite alive. “The fates of J.D. and Blake will ultimately decide the political fate of Peter in that they will dictate how involved he decides to be,” surmised one Republican close to Vance. “If J.D. and Blake are both successful, common sense tells you and logic tells you that it would likely make anyone say, maybe I should be more involved then. If two people who he really believes in and clearly thinks are brilliant guys, if they run and lose, there’s a different conclusion: Wow, these guys who are super brilliant and are great and are funded—and they still weren’t able to win. What am I really doing here?”

When I began reporting this piece all of six days ago, Thiel’s political fortunes seemed rather bleak. Vance, in particular, has been polling in the middle of the pack for months. Over the weekend, however, Vance suddenly received a jolt of momentum thanks to a somewhat surprising Good Friday endorsement from Trump. Vance, after all, was previously a vociferous Trump critic, back in the days when he was a regular on “Morning Joe.” But Thiel lobbied Trump directly for the nod of approval, I am told. The two have spoken several times in recent weeks, including at an in-person meeting a month or two ago. The Vance coalition was not led by Thiel: Tucker Carlson and Rep. Matt Gaetz were much more involved in securing the endorsement. Trump told one person that has spoken to him recently that Thiel’s opinion isn’t that important to him—Thiel isn’t in Trump’s inner circle, but in the circle just outside it.

Winning the Trump endorsement mattered more than winning another Thiel check. Still, I’ve been curious for months why Thiel hadn’t put more money into the Vance super PAC—Thiel committed $10 million in March 2021, and then didn’t make any more donations for at least a full year, according to updated campaign-finance reports made public last week. $10 million doesn’t go that far in Ohio, which has a dozen or so media markets. And so at the end of last month, the super PAC had only $300,000 left in its coffers for the final five weeks of the primary race. Despite some recent entreaties from the outside group, there had been no follow-up check. As a result, the super PAC has been off the air in the closing weeks of the race.

That was until the Trump endorsement crossed the wire. I am told that Thiel cut a major check to the Vance super PAC after the word came from Mar-a-Lago, allowing it to go back up on TV with $1.3 million in ads that hit the airwaves on Tuesday, according to the media tracking firm Medium Buying. (Politico later reported the precise check from Thiel to be $3.5 million in size.)

Decisions like these are ultimately Thiel’s. But the uncertainty about how much of a political animal Thiel wants to be stems, in part, from his rather sprawling network. There is a leadership vacuum that has led to “a lot of jockeying” among Thiel aides and associates in recent months, according to people familiar with the dynamic. Thiel’s political portfolio used to be overseen by Blake Masters, before he launched a bid of his own. Nowadays, Thiel frequently talks politics with Chris Buskirk, a conservative intellectual in Arizona who runs the Masters super PAC, along with Johnny McEntee, a former top Trump political aide. (Like Buskirk, McEntee is not currently on Thiel’s payroll. He is developing a Thiel-backed dating app for conservatives.) Thiel’s principal political aide these days is James Bacon, a former deputy of McEntee in the White House (and a grandson of the famous journalist of the same name), who functions less as a gatekeeper and more of as a tactician and liaison to campaigns. More broadly in ThielWorld, the most empowered aide is probably Jimmy Kaltreider, who informally succeeded Masters as Thiel’s right-hand. But Thiel’s primary sherpa, I’m told by sources, is Thiel himself—he is pretty hands-on, and typically makes the calls.

The vastness of Thiel’s orbit is also observed in how Vance and Masters are both often referred to as former “Thiel employees.” But despite mythologizing to the contrary, Vance and Thiel did not really have a close relationship until the last couple of years. Vance met Thiel in 2013 following a speech the billionaire gave at Yale Law School, and Thiel then set up Vance with an exceedingly-brief full-time job—a few months, really, just enough for Vance to officially describe himself as an investor on the dust jacket of Hillbilly Elegy in June 2016—at Mithril Capital, a venture firm, co-founded by Thiel but one where he was barely operationally involved. “Peter felt that [Vance] was a smart guy who could be a smart conservative who had zero platform, so let’s get him a platform,” speculated one person who was close with Thiel at the time. “Peter 100 percent knew [Hillbilly Elegy] was going to be a big deal.”

Of course, P.T. was correct. The book was not only a bestseller, but also a cultural touchstone for previously incurious Acela Corridor elites yearning for a Midwestern diner-style storybook understanding of the Trump voter. Netflix and Ron Howard optioned Vance’s book. Thiel would eventually stake Vance’s own venture capital firm—Thiel has served on the firm’s limited-partner advisory committee—and the two grew to be “extremely close,” as one person familiar with the relationship put it. As of late 2020 or so, J.D. and P.T. were in touch multiple times a week and seeing each other a few times a month, the person said. They have become legitimate friends—not political friends, or Silicon Valley friends, but actual friends, on par with Thiel pal Ann Coulter.

When Vance was signaling that he was running for the Senate, in the spring of 2021, word went out of a $10 million donation from Thiel. One Republican who has worked with Thiel said his involvement in a campaign or a cause is not just about the money, but about the legitimacy it conveys. “If Peter donates to you, you’re now viewed as viable,” said the Republican. “It does lead to a burst of excitement, and lets people know he cares about it. But ultimately the responsibility and burden falls on the candidate to flex the Peter endorsement more than anything else.”

Vance has indeed flexed the Thiel connection, well before the Trump endorsement, auctioning off dinners with Thiel in exchange for $5,800 checks—a lucrative gambit that certainly represented a new frontier in campaign finance, and one that also speaks to Thiel’s cult-like following with entrepreneurs on the right. Masters went even further, and was quite innovative, auctioning off not just dinners but an N.F.T. of the startup bible, Zero to One, that he co-wrote with Thiel.

Masters, for his part, is hoping to capitalize on the jolt of energy that Trump infused into Thiel’s network by endorsing Vance—and, presumably, hoping for an endorsement of his own. Vance called himself a “Never Trump guy” in 2016 and compared the candidate to Hitler. Masters, on the other hand, actually worked on the Trump transition team. One Masters friend pointed out to me that if Vance could get the Trump endorsement despite his well-publicized transgressions, then surely Blake could too, no? On Monday afternoon, Trump put out another statement not endorsing Masters, but blasting his main competitor, Mark Brnovich, and saying that he’d be weighing in on the Arizona race “in the not too distant future.”

That would certainly be a coup for Thiel, and a remarkable reversal of fortunes. It has struck some Thiel friends and political associates that Thiel has been working harder over the last year on behalf of Masters than he has on behalf of Vance. Indeed, one person close to Trump told me they were reliably informed that Thiel had delicately expressed to Trump that if he could only call upon one endorsement favor, it would be for Masters. Another person that interacts with Thiel’s team told me that he felt in recent months that the team was close to throwing in the towel for Vance, and channeling their energies on Arizona.

Even if Vance and Masters win their primaries, and then survive enormously expensive generals, Thiel’s larger political strategy, as one of his friends told me, remains “mostly conceptual.” There has been some hope—perhaps a mix of pressure and wishful thinking—from the professional right that Thiel would fill the void left by the Kochs and the Adelsons. Thiel is surrounded by people with various agendas, and he takes their advice, but he ultimately has his own interests to tend to. In the end, he is going to do whatever he wants. Like so many other political mega-donors in this extraordinary era of wealth creation, Thiel is in charge.

Accordingly, many fundraisers and operatives in Republican circles have been scrambling to broker introductions to Thiel directly over the last year or two. One project that Thiel has been involved with is a new donor coalition called the Rockbridge Network. But the group still strikes other Republicans as very nascent and vague, or “still in its infancy stage,” in the words of one G.O.P. operative familiar with it. Its $30 million budget sounds like a lot, but, as insiders know, it really isn’t. While the group has been organized by Buskirk, the Thiel associate, it’s not totally clear how committed Thiel himself is to the project.

After Ohio, I see two paths for how Thiel’s next chapter could unfold. Thiel could certainly be successful as a powerbroker. An under-appreciated part of Thiel’s influence is how much he is idolized by his peers. Despite the caricature of Thiel as a robotic, somewhat introverted German import, Thiel can be quite voluble, even charming, in private. Peak P.T. can be observed at the dinner parties he holds at his bicoastal homes, where he will often host conservative politicians and far-right activists. “Sheldon would’ve never done that,” observed one G.O.P. operative and a onetime Thiel dinner party guest. “He’s having political operatives and donors and business guys at the table. Sheldon would only deal with business guys.” Of course, P.T. has his own business guys: In November, Thiel’s friend (and fellow PayPal mafia member) David Sacks hosted a fundraiser in San Francisco on Vance’s behalf. (Sacks, working with a Washington hand at his venture-capital firm named Chris Massey, has gotten more involved in politics in the Biden era.) That same month, Joe Lonsdale, who co-founded Palantir alongside Thiel twenty years ago, co-hosted a fundraiser alongside Thiel and Sacks for Masters at Mar-a-Lago. Keith Rabois, another close Thiel buddy from Stanford, is a longtime Masters friend and has attended multiple events with the two in Miami Beach, where Thiel spends most of his time now raising two children in two adjacent mansions once featured on The Real World Miami, with tons of security.

The other possibility is that Thiel, having elected two allies who will take his calls, simply slinks off into the electoral sunset. That would disappoint many Republicans, including in his inner circle, who have tried to steer him toward a more Koch-like status. I spoke with one Thiel interlocutor who argued that his commitments to Masters and Vance represent the winding-down, not the winding-up, of his political engagement. If it was just a coincidence that Vance and Masters decided to run for the U.S. Senate at the same time—they both weighed runs in previous cycles—then is there really a grand strategy? This person told me that they believe the narrative about Thiel resigning from the board of Facebook’s parent company, suspiciously reiterated in almost every story about the decision to focus more on politics was false. “He made a commitment to support J.D. and Blake, and he is following through with that. But I would be surprised if he takes on new commitments,” said this person. “I think he’s re-evaluating. It takes a while to turn a ship, and that’s what you’re seeing.”

But a political victory for a mega-donor can be as intoxicating as owning a winning sports franchise. During the Trump era, Thiel spent about $3 million on behalf of immigration hardliner Kris Kobach in multiple Kansas races, and he lost twice. But Thiel, like any V.C. hoping for a 10-bagger, surely remembers how, with a mere $1 million bet on Trump in 2016, he reinvented the political landscape and transformed himself in the process. “It’s going to be a [small] sample size this year,” said one Republican operative close to Thiel’s team, imagining a future where Thiel spends hundreds of millions a cycle. “I hope he gets more involved, and I think he needs a couple wins first. He doesn’t want to throw his money down the drain.” Two weeks from today, Thiel faces his first test.