Donald Trump Was Peter Thiel’s Most Successful Investment

The tech billionaire’s early stake in right-wing candidates has produced enormous dividends. But for Thiel, it’s far more than a personal victory.

Carolyn Kaster/AP

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In 2004, Peter Thiel invested $500,000 in Facebook, money that quickly gave way to an unthinkable fortune for the right-wing billionaire. But it turns out that it was Thiel’s donation to Donald Trump’s 2016 campaign—and his willingness to speak in support of Trump at the Republican National Convention at the time—that has produced perhaps the biggest dividends, transforming him into a genuine oligarch of American politics.

Now, you won’t hear about this in such explicit terms when Trump officially accepts the Republican presidential nomination. But Hulk Hogan’s unexpected appearance on Thursday, shortly before Trump takes the stage, makes the message unmissable. In fact, Hogan’s appearance, which would make him the third Thiel acolyte to be on stage at the RNC this week, is an effective middle finger to critics.

To understand this dynamic, one must reach back to a 2007 online article headlined, “Peter Thiel is totally gay, people.” The piece, published by Gawker Media, had outed the billionaire Palantir-founder and prompted a series of similar articles about Thiel’s private life. To most people, that may have seemed like the end of it. But then in 2012, Gawker published a sex tape featuring Hogan; $10 million in legal help from Thiel later, Gawker was dead—the right-wing billionaire’s retribution was complete.

It was around this time that Thiel was delivering a speech at Yale Law School, where a bright-eyed J.D. Vance watched with apparent amazement. The encounter led to a job at Thiel’s investment firm. Later, even before Vance announced his campaign for Senate in Ohio, Thiel gave $10 million to a super PAC backing Vance’s bid. As my colleague Noah Lanard reported back in 2022, that early investment into Vance’s political career—coupled with his critical role in helping Vance, a former never-Trumper, smooth out his relationship with Trump—proved successful.

Fast forward to 2024, and Vance, the illiberal, deeply anti-abortion, right-wing author of Hillbilly Elegy could be in the White House—ensuring that MAGA politics will long outlast Donald Trump.

But it would be misguided to see all of this as personal enrichment. As Thiel told the Times after effectively bankrupting Gawker: “It’s less about revenge and more about specific deterrence. I saw Gawker pioneer a unique and incredibly damaging way of getting attention by bullying people even when there was no connection with the public interest.”

The same is likely true for Thiel’s political ambitions. He doesn’t see his fight as a means for personal benefit. For a man who has publicly said that he doesn’t believe that freedom and democracy are compatible, Vance, Trump, and Hogan are vehicles of his ideological ambitions. And when you invest early like Thiel did with Vance, you can receive unthinkable rewards.

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