Welcome back to The Stratosphere.

Happy Tuesday from the friendly skies. As always, if you’d like to get in touch (or want to pass along a confidential tip), you can reach me by replying to this email.

In today’s column, a look at the political reverberations of a friendship that began three decades ago in a sophomore philosophy class, and now hovers over one of this year’s big U.S. Senate races. And check out the latest episode of The Powers That Be, Puck’s new daily podcast, for my conversation with Tara Palmeri about Biden’s evolving relationship with Silicon Valley, Kamala’s fundraising challenges, and who really has the juice in Wilmington West.

Three decades later, the two billionaires are still fighting over politics—just now by proxy. Today, both former PayPal executives, who remain close friends, are on opposite sides of one of America’s most closely-watched Senate races in Ohio, one of several states that could determine control of Congress next year. Thiel, of course, has pumped $15 million into groups backing J.D. Vance, the Hillbilly Elegy author and Thiel mentee who has become a Fox News favorite. Hoffman, meanwhile, is less interested in Democratic nominee Tim Ryan than in gleaning voter insights from Ohio itself, which his team hopes to deploy in other Rust Belt states in 2024. “This has been a hobbyhorse of theirs,” said one person familiar with their strategy. “They are obsessed with Ohio, and they want to fund and experiment in the state.”

Despite their differences, both Thiel and Hoffman are motivated by the same underlying assumption—that Vance is a heavy favorite in a Trump +8 state, and that it would take something close to a miracle for Ryan to win. That’s partly why Thiel has signaled some early reluctance to spend much more of his own money on the general election. Why bother when the race is already won? Ryan’s relative weakness also helps to explain why Hoffman’s team is able to A/B test new messaging and tactics in the state: Whether or not they can get him elected, they’ll have learned something important.

Ohio is a similarly alluring staging environment for Hoffman because so few national Democratic groups are likely to spend big money there, allowing Hoffman’s team to treat the state as a controlled experiment with minimal exogenous variables. (The same is true to a lesser extent in Utah, where Team Reid is pondering experiments to support independent Senate candidate Evan McMullin.) If other big Democratic outside groups like EMILY’s List, Senate Majority PAC, etc. were also injecting money in the Cleveland or Youngstown media markets, it would theoretically complicate Hoffman’s ability to discern whether it was his money that moved the needle. There is another big statewide race in Ohio, G.O.P. governor Mike DeWine’s reelection bid, but he is running away with the race and so there’s unlikely to be major Democratic spending there either.

Hoffman’s team, understandably, declined to spell out the exact nature of these experiments they’re cooking up, although I’m told Hoffman himself hosted a briefing this month for major donors and their advisers to discuss his political bets, including strategies for Ohio and Utah. But I do know that testing new party messaging has been a priority for Dmitri Mehlhorn, Hoffman’s smart, data-driven, and somewhat controversial donor-advisor. Mehlhorn and Hoffman, after all, have both been concerned that the activist class has been providing too much fodder for Tucker Carlson, so much that last month Mehlhorn wrote a much-forwarded email to some progressive groups informing them that his donors were essentially cutting them off going forward. “The short overview is that we were happy and proud to invest in infrastructure in 2017-2021 to resist Trumpist fascism. Today, I think such organizing is less likely to be effective, and much more likely to actually hurt us in our efforts to fight off the fascists,” he wrote. Mehlhorn recalled that Biden was actually looking pretty good before the summer of 2021. “Had the groups that built power on the left simply taken a long nap, we would be living today in a less difficult environment.”

As I reported back in April, Hoffman and his team recently helped to launch a new outside group this cycle, Mainstream Democrats PAC, that is focused on sidelining progressive candidates that Hoffman views as less electable. Ryan, after all, is exactly the sort of moderate, middle class candidate that fits the Hoffman mold. He’s been a congressman since 2003, briefly ran for president in 2020, and a poll last week showed him down by just three points. In a more favorable year for Democrats, the party would likely rally to his cause. But Democrats this cycle have to decide which of their candidates are most competitive, and with Biden’s polling underwater, the party apparatus is in triage mode. And that’s to say nothing of the fact that party-affiliated committees generally need to prioritize re-electing incumbent senators, which Ryan, unfortunately, is not.

Given the fundamentals in Ohio, Thiel has in many ways already won. Indeed, even if Thiel took a long nap through November, Vance would likely win in the fall. Thiel didn’t get rich by wasting money—in fact, he can be fairly cheap—and he has got to know that it’s superfluous at this point. So it was a bit amusing to hear that groups aligned with Mitch McConnell, including the Senate Leadership Fund, have been approaching Thiel to persuade him to finance their ad spending on behalf of Vance and other Thiel-backed candidates. One source described a request from Team Mitch in the neighborhood of $20 million, in late April, after Vance had already secured Trump’s endorsement and was on track to win the G.O.P. nomination. Needless to say, Thiel hasn’t yet written that check.

Of course, it’s the job of fundraisers to make aggressive asks and anchor high, but I don’t see why Thiel would trust an establishment creature like McConnell to manage his money. Big donors these days cherish control in the post-Karl Rove era, and Thiel in particular already has his own bespoke super PAC in Ohio, run by a well-regarded G.O.P. operative, Luke Thompson, that could spend Thiel’s money in the state if he really wanted to. But he probably doesn’t need to.

That money would be better spent in Arizona, where Blake Masters will face a competitive and undoubtedly expensive general-election battle against incumbent Senator Mark Kelly—if he manages to survive two months of what is sure to be furious oppo and win the Republican primary. But McConnell’s campaign infrastructure wouldn’t be the right fit for Masters, anyway, especially given that Masters declined (notably, just before receiving Trump’s endorsement) to commit to supporting McConnell for majority leader. Thiel has his own super PAC in Arizona, too, and doesn’t need someone else’s help in the state. That’s what having your own money is for.