Silicon Valley

“Does He Believe Chaos Is a Ladder He Can Climb?” Trump-Enabler Peter Thiel’s Dinners Are the Hottest Ticket in L.A. So What’s His Endgame?

Undeniably curious, ecumenical in his taste in people, scourge of Gawker, the tech billionaire has captivated some of his ideological opponents with a series of TED Talk–like dinners. In the Los Angeles Game of Thrones, he’s Littlefinger.
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The hottest ticket in town in Los Angeles these days isn’t what you’d imagine. It’s not an invite to the opening of Christian Marclay’s Snapchat-driven art installation at LACMA. Or an opportunity to walk the red carpet with Joaquin Phoenix and Robert De Niro at the premiere of Joker. And it certainly isn’t a fortuity to attend one of the countless fundraising soirees by presidential nominees in Beverly Hills or Hancock Park, where, for the cost of a down payment on a car, you can take a selfie with Kamala Harris, Elizabeth Warren, or Pete Buttigieg. Counterintuitively, in this way-beyond-liberal city, the hottest ticket is an invite to a dinner hosted by one of the people who helped get Donald J. Trump elected in 2016: Peter Thiel.

When Thiel very publicly renounced Silicon Valley a year and a half ago, his central complaint was that it had become a monoculture, which, even given the movie business, Los Angeles definitely isn’t. Not everyone is eligible for a meal with Thiel. He doesn’t entertain fools at these dinners (with the exception of one recent supper with one very big fool, which we’ll get to in a bit). The dinners don’t just take place in L.A., though, as of late, most have. (Thiel owns homes in L.A. and New York, and a hideout in New Zealand.) But Hollywood has recently become his hub of choice, where he has drawn-out dinner parties with an eclectic variety of guests, from WWE wrestlers to authors, investors, entrepreneurs, celebrities, podcasters, and tech titans. The dinners are almost always catered by Thiel’s chef, who regularly travels with him to his homes, and the meals are often a paleo-themed affair. The food, said one person I spoke with who attended a dinner, is “quite delicious, actually.” Where things get interesting is in the conversation.

In many quarters, especially liberal ones, Thiel is seen as a right-wing super-villain, rich and smart and evil—mostly evil, starting with his role in helping Trump get elected. Then there was the secret backing of Hulk Hogan’s devastating lawsuit against Gawker Media, nearly 10 years after the outlet wrote an article about Thiel's sexual orientation that he seems to have taken slightly personally. (Although by no means does everyone mourn the fall of Nick Denton’s mean media empire.) Others decry him for cofounding Palantir, a big data behemoth with government contracts, which has been labeled by some journalists as one of the most terrifying companies in Silicon Valley. And then there’s the compendium of politically paleo ideas Thiel has vocalized in the past, like his belief that allowing women to vote was bad for democracy (he later added that it would be “absurd to suggest that women’s votes will be taken away”), or, shortly after Trump won, that people should take Trump “seriously, but not literally”.

But there are also attributes about Thiel that people genuinely like and respect—often people who resent him for one, or all, of the above. He’s an undeniably curious person. He’s obsessively interested in deep discussions about an array of topics, from global issues to economic, technological to societal. Unlike some liberals of his stature and influence and wealth, who only want to talk to people with like-minded viewpoints so they can understand how to destroy their opponents, Thiel seems to have a genuine interest in contrarian conversations, and not just for the sake of argument. He really wants to engage people in hearing differing viewpoints about everything affecting society today and in the future, from foreign affairs to China–U.S. relations and the role A.I. will play in modern medicine and on the battlefield—pretty much any topic you’d find discussed in a Washington think tank. One person who has been his dinner guest said Thiel requires that people use what he calls “steel-man arguments versus straw-man arguments,” and, this person noted, the meal discussions “are never gossip about other people.” Which leads us to that one dinner with that one fool.

During a recent interview with Fox Nation’s Uncommon Knowledge, Thiel told host Peter Robinson that he plans to endorse Trump for president in 2020. But according to two people who have spoken with him recently, he doesn’t think Trump is all that bright, an opinion he shares with many of his tech and Hollywood peers. When he has dined Trump (which apparently happened a couple of weeks ago), it wasn’t the typical conversation of a Thiel dinner, and instead focused on a whole lot of straw-man arguments about unimportant topics, and even gossip about other people, especially media personalities, whom Thiel has little interest in.

Three people who have spoken to Thiel recently told me that there is absolutely no way he sees Trump as an intellectual peer. As one of Thiel’s former dinner guests said, “Trump is a means to an end for Thiel. As human beings, they couldn’t possibly be more different,” the person observed. “I can imagine that a Trump–Thiel dinner is the exact opposite of how Thiel likes to dine: Thiel likes to opine and entertain differing viewpoints; Trump only wants to talk about himself.” As BuzzFeed’s Ryan Mac has reported, Thiel is still unsure how he really feels about Trump, though Thiel won’t say so publicly.

The contempt one imagines Thiel has for Trump’s intellect leads to another question, this one about Thiel and his own political ethics. “Was Thiel ever really a supporter of Trump?” one entrepreneur who has spent time with Thiel asked me rhetorically. “Does he believe that chaos is a ladder he can climb? Thiel is playing chess while we’re playing checkers.” The entrepreneur, whose political views are essentially the opposite of Thiel’s, noted that talking to him is actually rather enjoyable. They described him as charming, clever, and contrarian. But the person also likened Thiel to Petyr Baelish, known as “Littlefinger” in the TV show Game of Thrones. In the entrepreneur’s viewpoint, Thiel’s support of Trump isn’t about Trump’s diabolical governance and frantic tearing apart of society and democracy for his own gain, but, rather, that Thiel is likely—and this is just an educated guess—benefiting, either financially or intellectually, from the crumbling of society as we know it.

Few who know Thiel are at all surprised at this hypocrisy—he’s known as a person who can say one thing at a private dinner, and something entirely different in a public forum. Thiel’s private dissimulations were on clear display recently during the Fox Nation interview, when Thiel talked about how much he hates politics, telling the host: “I would like us to be honest about how terrible politics is. As someone who is generally libertarian, I would like to live in a world that is less conflict, less politics.” But obviously, patently, he loves politics. He enjoys playing in that sandpit more than most people who made their fortunes in Silicon Valley. He’s constantly giving talks and doing media hits to share his political viewpoints. Last month, he co-hosted a fundraiser at his New York City apartment with Ann Coulter for Kris Kobach’s 2020 Senate campaign. And yet Kobach is a paleoconservative—too red even for Kansas. As secretary of state there, Kobach implemented some of the strictest voter identification laws in the U.S., including fighting to have almost 20,000 registered voters removed from the state’s voter rolls. At one point he was floated to fill the role of Trump’s “immigration czar,” a post that would be created especially for him. Kobach perhaps didn’t get the job because he demanded a 10-point list of conditions to take it, including a West Wing office, a security detail, a 24-hour access to a government jet, and walk-in privileges with Trump. The less said about Coulter and her “politics,” the better—except that she has now gone full anti-Trump. One can only imagine what Coulter and Thiel talk about at dinner.

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