McConnell & Thiel’s Game of Chicken

Happy Tuesday, welcome back to The Stratosphere.
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Welcome back to all of those not on the Playa.

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Today, fresh, inside-the-room reporting on the high-stakes, big-money negotiations between Peter Thiel and Mitch McConnell over the G.O.P. campaigns of J.D. Vance and Blake Masters. Read through to see what people like Josh Holmes are saying about Thiel, and about a top Thiel aide who was recently fired from his gig.

Speaking of Thiel, he did host his tricked-out PayPal Reunion party this past weekend at his palace in Bel Air with a red carpet, a long row of chess boards meant to emulate the famous festivities of PayPal’s I.P.O. day 20 years ago, and t-shirt gifts reading “X.com” on one sleeve and “Confinity” on the other (the two companies that merged to form PayPal back in the day). And yes, Thiel’s PayPal-era enemy, now kinda-sorta friend, Elon Musk, was there. The two caught up at the event.

Now onto more consequential Thiel news…

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Can Thiel and McConnell Strike a Deal?

As Republicans unexpectedly labor to retake the Senate, the standoff between Thiel, the consummate contrarian, and McConnell, the consummate pragmatist, has suddenly become one of the most important relationships in the G.O.P. financial universe. Who is going to foot the bill for Vance and Masters: their ole mentor or potential future boss?

TEDDY SCHLEIFER

After a lengthy vacation in Europe, followed by a blowout PayPal reunion party at his mansion in Los Angeles last weekend, Peter Thiel has returned to reality to deal with more immediate concerns: How to elect his two Republican protégés to the U.S. Senate.

Thiel has had an incredible run in the 2022 midterms cycle, placing two $15 million bets in Ohio and Arizona to transform J.D. Vance and Blake Masters, respectively, from middle-of-the-pack primary candidates into G.O.P. Senate nominees. But behind the scenes, sources familiar with the talks tell me, Thiel’s team has spent the summer engaged in months-long, high-stakes, sometimes tense negotiations with allies of Mitch McConnell about who is going to finance the advertising barrage required to carry Vance and Masters over the finish line. As I previously reported, McConnell’s team reached out to Thiel around late April for another $20 million, to be deposited in McConnell’s super PAC, to boost the two candidates through November. That didn’t happen. Thiel, despite being worth some $7 billion these days, can be surprisingly frugal—and, apparently, highly sensitive to feeling extorted. After all, isn’t it McConnell’s job to elect G.O.P. nominees?...