Over the past few days, billionaire Peter Thiel and Senate Minority Leader Mitch McConnell have found themselves in a feud over funding Thiel’s endorsed Senate candidates in Arizona and Ohio. Earlier this year, McConnell urged Thiel to pour more money into a super PAC backing J.D. Vance, as Republicans fret over money disparities in Senate races across the country. Thiel refused, fueling frustrations among Republicans that the wealthy Thiel was abandoning the candidates he wanted Republicans to nominate at a critical juncture in the campaign cycle. Thiel’s decision highlights an ongoing tension between top Republican strategists and lawmakers and one of the party’s most deep-pocketed donors.
To dig further into the megadonor’s mindset, we spoke with Max Chafkin, author of The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power, which has come to be regarded as the definitive biography of Thiel. Although Thiel’s interactions with McConnell are rarely brought into the spotlight, Chafkin’s book offers an unrivaled look at the ideas that drive Thiel’s political projects.
We spoke with Chafkin a day before McConnell headlined a fundraiser for Blake Masters, the Trump-endorsed U.S. Senate candidate from Arizona. A condensed version of this interview was published in this week’s edition of The Run-Up, TNR’s weekly campaign newsletter. This interview has been edited for clarity.
It feels like Thiel is at a much more elevated level than he was previously as a donor. In the past he seemed like one of those deep-pocketed wealthy donors who funded fringe candidates who always lost. This time it’s very possible that at least one of the candidates he’s propped up will become a senator.
Putting money that he put into Trump’s campaign in 2016 and getting the profile that it gave him, both within conservative politics and then also in Trump world, that, I think, was kind of the beginning of this. That was his first big political success. Up until that point, it really was long shots—kind of these obscure causes, things like that. As I wrote in the book, he had this PAC to help Ron Paul in 2012, and it was a complete failure. I mean, they did some innovative things; they targeted some innovative races, but it went nowhere, and I think Thiel has always wanted to be more central to the conservative movement.
Post-2020, I think a couple of things happened. One was there was this opening created by January 6 and the end of the Trump presidency for someone like Thiel to come along, where you have this obvious constituency for these hard-right ideas—but not a lot of people, besides Donald Trump really, trying to claim it. And especially when you look at the donor class, they had mostly tried to back away from Trump. So I think, for Thiel there was kind of an opportunity there to raise his profile, and he did it in this very weird way, by writing these gigantic checks to former employees, neither of whom had any obvious business running for Senate. Vance, of course, had a little bit more of a profile. He wrote this successful book and everything but hadn’t done a whole lot besides that. And then Blake Masters, he was Thiel’s top assistant. He’s someone who’s more or less been Thiel’s right-hand man for a decade.
Was he only drawn to Vance and Masters because they are employees? Were their politics particularly enticing to Thiel?
Thiel’s whole playbook, for his entire career in business, is about networks and finding people who have worked for [him] before and giving them bigger jobs. He’s actually very good about going out and settling them in parts of his empire. He has a type, and I think in lots of ways Masters and Vance fit that type, and I think it’s not that surprising that they first found their way into his orbit and then used that to catapult them to positions of political prominence. Obviously Thiel is capable of backing people who aren’t his employees because he backed [Kris] Kobach, but I think the fact that they are very much close to him, loyal—especially in the case of Masters—longtime aides, that plays a big role in it.
How surprised are you that Thiel finds himself at odds with McConnell, since Thiel is so interested in sort of establishing himself in the GOP donor ranks?
In some ways that was the whole point. Early on in the campaign, he had a fundraiser. Alex Isenstadt reported on it. It was for [Harriet Hageman]. He talked about, basically, that the first step to what they are trying to achieve is focusing on the Republican Party itself. It was basically about rooting out these bad institutionalists. That was something that was going on in the early days in the Trump administration as well, when he allied himself with Steve Bannon and it was very much about installing hard-right ideologues in positions of influence and power, rather than these kind of more normie, mainstream Republicans. And with Masters and Vance, they both have framed their candidacies not just in terms of Democrat versus Republican but also kind of New Right versus Old Right, and they were going to be these figures who were going to bring new energies and get rid of the old pieties of conservatism. In some ways, [Thiel] picked these candidates because they were at odds with McConnell and they were not “electable Republicans.”
I do think in some ways it’s not at all surprising that Thiel would try to foist the general election expenses on Mitch McConnell and Republicans.
It’s very much in line with the venture capital business model. Venture capitalists put early investments in high-risk assets. They buy cheap, and they buy when the thing is at its most unstable position, and then later stage investors come in and take the company to its IPO. So it makes a certain sense, in that respect. And also, when I was writing the book I reported there are lots of instances where Thiel would seem completely committed to a given company or person and then would be totally willing to walk away as part of a negotiation to protect his assets or stake. He’s Machiavellian, and this is sort of a Machiavellian move. He’s put Mitch McConnell in a real bind. The thing is, Thiel himself is in a real bind. And yeah, it’d be a real shame for McConnell if Republicans don’t take the Senate, but it could also be very bad for Thiel.
The 2024 elections aren’t that far off. Has there been any indication on which way Thiel is leaning in the Republican primary?
Well, there’s a question of what is Thiel going to do in his heart of hearts, and what is Thiel going to actually do? And I think those are two different things. This probably applies to a lot of Republicans. Thiel really likes Trumpism. He likes the sort of hard-right, populist brand of politics. He likes the anti-woke pose. He likes the propensity for trolling. He likes the anti-immigration stuff. I think he sees a lot of potential—I don’t know what you’d call it: synergy?—with some of the nationalist economic policies where there’s a real opportunity for him and his companies to benefit from this potential shift. I think he likes Trump, but I don’t think that’s the thing that he feels the most affinity toward. I think the thing he feels most affinity toward is Trumpism, not Trump himself. So if you could somehow create a Trumpist candidate who is more disciplined than Donald Trump—
That’s Ron DeSantis.
Right, that’s DeSantis. So I think on some level, sure, Thiel would be very happy if somewhow Trump could be eased out of the race in a nonconfrontational way where all that support could go to DeSantis. But it’s pretty hard to separate Trumpism from Trump. I think Thiel’s aware of that, and if anything the primaries have shown just how hard it is to separate Trumpism from Trump, and where we have candidates that seemed very much like Trumpist candidates, but they didn’t have support from the big man, and they lost. Thiel’s guys played this game really well on going full bore on election denial and really embracing Trump himself, not just the movement.
I think, basically, Thiel is going to play this practically, which is he’s going to try to avoid taking a side until it’s clear where the chips are going to fall. But I don’t think he’s going to break with Trump for the sake of breaking with Trump. And if Trump is running, it’s very hard for me to see Thiel play an active role in opposing that.
As far as you know, what is the song and dance for candidates to endear themselves to Thiel? Does he have some kind of political adviser who directs all these things?
Well, Thiel doesn’t have much of a—it’s gotten maybe a little bit more disciplined in recent years, but he’s never really had a political team in the way other billionaires do. Ultimately he is the decider with a lot of these checks, and he has his inner circle of people who work for him at Thiel Capital, which is his investment fund, and then like friends and so on. It’s more like the court of a king. The upside is he can exert a lot of influence without doing a lot of work because you have some people who’ve gotten money from him and continue to stay in his good graces, but you have lots of people who are auditioning for his money.
I mean the simplest way would be getting attention in one way or another for being anti-woke, or by being a really smart young thinker in conservative politics, or being a superinnovative technologist. A whole range of possibilities. So I think a lot of this is happening without his direction necessarily.
I brought up Vance coming out in favor of crypto. Did Peter Thiel tell him to do that? My guess is probably not. If you’re Vance or some of these people who are dependent on his support in one way or another, you end up constantly trying to shape your positions or actions that are designed to please him and stay in his good graces. He’s kind of cultivated this mercurial personality, which creates power because there’s lots of people who are dependent on him and can’t predict what’s going to happen.
Does Thiel still watch fantasy? Does he watch Lord of the Rings and Game of Thrones? Why does he name everything after various things from J.R.R. Tolkien?
Well, a couple of things. I think he is fond of the books and he’s a fantasy geek. When I was reporting the book—this nugget is out there, but when I was reporting the book, I was kind of interested in this. I got a copy of Thiel’s senior yearbook, which has his quote, “The greatest adventure is what lies ahead, today and tomorrow are yet to be said.” Now Thiel has said this is his favorite passage from Tolkien. Do you know where it’s from?
Well it’s not from Tolkien, it’s from the animated adaptation of The Hobbit created by the guy who created Thundercats. I don’t think his knowledge of this stuff is necessarily that deep. Like I said, I think he’s a fan of this, I think he cares, but my theory is that some of this is about creating an affinity group. He recognizes that he’s an amazing brand builder and storyteller and creator of mythology. I think he recognized that for a certain subset of geek that he really cares about and is important and influential, Tolkien and Lord of the Rings is big. I think it’s as much about in-group signaling as anything else.