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The Achilles Thiel

Peter Thiel
Peter Thiel put millions of dollars behind J.D. Vance and Blake Masters to win their respective Senate races. Photo: Marco Bello/Getty Images
Theodore Schleifer
November 9, 2022

It was just before Labor Day, and Senate hopeful Blake Masters had spent much of the summer getting absolutely shellacked with negative advertising in Arizona. Thousands of miles away, his financial patron Peter Thiel was enjoying a late summer tour of Europe and planning a decadent party to celebrate the 20th anniversary of PayPal’s I.P.O., the liquidity event that helped introduce a plethora of future tech patrons (Elon Musk, Reid Hoffman, David Sacks, et al.) into the economic stratosphere. But Thiel’s team, based out of his family office in Los Angeles, was nevertheless hard at work, vetting a proposal to drop another $20 million on Masters and J.D. Vance, a fellow Thiel protégé, to boost their struggling Senate campaigns. It would have been a monumental investment, and one that would have transformed the G.O.P. advertising landscape all across the country. But it never happened.

The pitch, formulated by a trusted, well-regarded Thiel-backed operative named Luke Thompson, was to put $20 million into a nonprofit that would then disburse about $4 million to a pro-Vance super PAC, $4 million to a pro-Masters super PAC, and split most of the remainder on “issue ads” boosting the two candidates in the states. Part of the strategy was to preserve Thiel’s anonymity—the provenance of the nonprofit’s money wouldn’t be disclosed, and the nonprofit could run the issue ads as long as they aired before mid-September. But by late August, Thiel’s team ultimately passed—and the proposal, which hasn’t previously been reported, fell apart.