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?