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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…

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?

And so, for the last few months, the standoff between Thiel and McConnell has become a game of chicken. But time is running out: It is almost Labor Day, and both of the Thiel-funded PACs supporting Masters and Vance are effectively broke, with neither having ads reserved in either Arizona or Ohio for the final weeks of the race. Some G.O.P. insiders and pro-Thiel forces, facing the prospect of fumbling the Senate, are wringing their hands over who exactly will be spending the money needed to beat Mark Kelly in Arizona and a surprisingly competitive Tim Ryan in Ohio.

The relationship between Thiel, the consummate contrarian, and McConnell, the consummate pragmatist, has now unexpectedly become one of the most important storylines in the G.O.P. financial universe. I am told that McConnell and Thiel have spoken directly and frankly about the situation over the course of the summer. Some sources I talk to swear we are on the cusp of an imminent breakthrough. Others are more dour and think this months-long stalemate may not be resolved until the fall.

The conflict is not just about money and polls, but control. Thiel’s candidates have their own super PACs, staffed by operatives that Thiel trusts, that he supplied with $15 million each over the course of their campaigns. Both demonstrated their mettle during the primaries with come-from-behind victories. If Thiel tops off those PACs with more money, he would retain the ability to focus his spending on Vance and Masters, the only two races he cares about, and to control the messaging around the general election. Thiel also cares about optics, and it’s a better look for his candidates to get McConnell’s stamp of approval, and not just that of some California-dwelling, Facebook-investing, billionaire venture capitalist.

The problem, as Thiel himself learned over the past few weeks, is that McConnell is in triage mode. Donald Trump boosted a handful of baggage-laden, neophyte candidates, including Herschel Walker and Dr. Oz, that are at risk of losing otherwise winnable races. Democratic Senate campaign fundraising has outpaced Republicans for months. And then there was the Supreme Court’s decision on Roe v. Wade, which ignited not only progressive voter activism but also millions of conservative-leaning moderates and independents who remain pro-choice. So any dollar that McConnell can convince Thiel to spend for Vance and Masters is another that he can spend for Walker or Oz. G.O.P. leadership is being forced to make strategic decisions about which of the half-dozen races they are monitoring are the likeliest to deliver a Senate majority, not what is best for Thiel.

This Sophie’s Choice situation is doubly painful given the genuine rapport that Masters and Vance have developed over the last several years as co-ascendant millennial members of what is today called the New Right. As I wrote back in November, Masters and Vance have traded staffers on both the campaign and super PAC sides, the two candidates co-wrote an op-ed together going after Thiel ally Mark Zuckerberg, and they set up a joint fundraising account when they hosted a New York fundraiser together last year. They are friends, and they text frequently. I wonder what those texts say these days, now that Vance’s fundraising struggles are jeopardizing Masters’s bid.

Masters was always going to be the tougher slog of the two races, but McConnell’s team, I’m told, has been more pessimistic than Thiel’s about Masters’s chances in Arizona, a deeply purple state with two Democratic Senate incumbents. As could easily be forecast, Masters has had to scramble to pivot his campaign messaging away from the hard-right messaging that defined the primary race. Since then, Masters has clumsily worked to tone down his more extreme stances on abortion and the 2020 election, among others, deleting some positions from his website. He’s even softening his rhetoric against McConnell, whom he wouldn’t commit to supporting for Majority Leader when asked this summer (a position that, notably, came right before Trump gave his endorsement). Two weeks ago, Masters told the AP that he knew he was “not Mitch McConnell’s favorite candidate” but that “I think he’ll come in and spend” to win the state.

Then, just a few days later, McConnell did the opposite, as news emerged that his super PAC had scaled back its investments in Arizona. NRSC chair Rick Scott, despite starting up some coordinated ad buys for Masters this week, also reportedly told him to get it together and raise more money on his own. All of this commotion has freaked out the Thiel universe. Masters, after all, is consistently down in public polling—but he’s not that far down. The race is, in the broadest sense, still winnable. Is the G.O.P. collectively really going to drop the ball? “Having gotten these guys to the final lap of these races, you’d think he’d want to win,” a McConnell ally said of Thiel.

Chris Buskirk, the it-boy G.O.P. operative leading the Masters super PAC, has been working the phone hard with other donors recently, I’m told. “Blake does not have a path if no outside money comes in,” said another Republican consultant supporting Masters. “If a month goes by without outside money, then he may end up in a situation that’s insurmountable. He’s down—but is he down because Kelly is too strong or is he down because of the disparity in money? And is the best solution to that really just to give up and let that disparity widen?”

So where does this end? Most insiders expect Vance to ultimately pull out the win in Ohio, especially now that he has $28 million worth of air support. McConnell’s nonprofit, One Nation, is still airing $5 million worth of ads bashing Kelly in Arizona, including in a new ad today. But the critical person to watch on the McConnell side, besides Steven Law, is Josh Holmes, McConnell’s top political aide and a key decision-maker at S.L.F. who has been open about his near-outrage if Thiel doesn’t get more involved. He said so publicly on an episode of his popular Ruthless podcast earlier this month. “Peter Thiel wants to win this race. He’s going to commit millions and millions of dollars,” one of Holmes’ co-hosts uttered confidently. “That better be the case,” Holmes shot back with more uncertainty, “because Democrats are outspending Republicans 4-to-1 at this point, and there is no place that is more the case than in Arizona.”

Thiel’s circle, meanwhile, includes a hodgepodge of friends ranging from Ann Coulter to Ric Grenell. He has a fairly small political staff. In fact, Thiel quietly lost one of his top aides earlier this summer. After a decade working for Thiel, the well-liked Jimmy Kaltreider was fired from Thiel Capital and the Thiel Foundation, where he is the executive director, earlier this summer, I am told, over both personal and political alignment issues. Kaltreider’s move hasn’t previously been reported, and he’s still listed on the Thiel Foundation website. He didn’t return a request for comment.

Thiel himself is keeping a busy political schedule for the fall: He has at least two political speeches on the docket next month, one a keynote address at the National Conservatism Conference in Miami, and the other at a California conservative gala in the Bay Area a few weeks later. In addition to his own fundraiser for Masters, I reported last week that two of Thiel’s close friends from the PayPal Mafia, David Sacks and Keith Rabois, are hosting a fundraiser for Masters, Vance, and a half-dozen other G.O.P. Senate candidates; maybe Thiel, who lives much of the year in Miami, shows up too. (In a memo distributed to possible donors for the event that I saw, the NRSC still described Arizona as one of its top-four pickup opportunities and described Masters as “the CEO of Thiel Capitol”—an inaccurate job title that Masters has renounced, and yes, a misspelling of the family office—“an investment management firm started by tech executive and Republican donor Peter Thiel.”)

But at its most fundamental level, the brinkmanship between Thiel and McConnell boils down to different visions for the Republican Party. Thiel, the 54-year-old, German-born tech iconoclast, wrote a $100,000 check to the S.L.F. in 2020, and once criticized Twitter’s decision to temporarily freeze McConnell’s account as “totalitarian,” but he has primarily supported MAGA groups, along with those like the Club for Growth, that have been thorns in McConnell’s side. The G.O.P., for Thiel, is merely a vehicle for his political goals. But for McConnell, the elder statesman, the dominance of the G.O.P. is the goal itself. He wants to elect 51 Republican Senators, by any means necessary. Thiel wants to elect his two protégés. The marriage of convenience is in the middle of that Venn diagram, if the two can find it.