But as the 2022 midterm cycle heats up, Thiel is winding down, according to two people familiar with the matter.

“He’s done for the cycle. He’s not putting any more money into any more races or getting involved in new races,” said one person familiar with Thiel’s plans who spoke to CNN on the condition of anonymity to describe private conversations.

Thiel, who has contributed more than $25 million this cycle, has been satisfied with the returns on his investments so far, said a second person familiar with the matter. Vance is heading to a general election. Arizona Senate Republican hopeful Blake Masters, who co-authored Thiel’s 2014 book “Zero to One” and who has also been bankrolled by the tech leader in his race, appears poised to receive a Trump endorsement ahead of his state’s August primary. And two congressional challengers whom Thiel has also supported — Joe Kent in Washington and Harriet Hageman in Wyoming — have mounted competitive bids against incumbent Republicans who voted to impeach former President Trump.

“I don’t think the level of support that he’s given Blake and JD is going to be at all reflective of that activity in the future,” said one of the people familiar with the matter.

A Thiel representative did not immediately return a request for comment.

Of the eye-popping sum Thiel has spent so far this cycle, more than $20 million went to super PACs supporting Vance and Masters, both of whom have embraced Trump’s lies about the 2020 election and are patrons of the “America First” agenda.

“I think people are underestimating how much his personal friendship with these guys has to do with his activity and level of involvement,” this person said.

Of course, the tech tycoon could still reverse course. A Trump endorsement and primary win for Masters could be a rousing scenario that lures Thiel back into the game if he feels he can have a significant impact elsewhere, as could a situation in which Masters or Vance find themselves struggling in general election contests. Either way, the entrepreneur-turned-populist firebrand has demonstrated his potential as one of the most powerful forces in Republican politics and an influential advocate for the strain of Trump-style populism that guides the candidates he is backing.

People close to both Thiel and Trump expect the billionaire tech investor to remain quietly involved in the political arena even if his financial contributions slow down, citing his proximity to the former President and the likelihood that he would serve as an informal advisor to Masters and Vance should one or both make it to the Senate. Trump and Thiel have huddled at least three times in the last year at the former President’s properties in New York, Bedminster and Palm Beach, according to people familiar with these meetings. And though they are not as close as some might imagine, the two men have quite a bit of crossover between their aides and advisers. Former White House director of presidential personnel Johnny McEntee, for example, reportedly secured funding from Thiel for a dating app he created and regularly speaks to both men, while other informal Trump advisors were deeply involved in working to elect Vance.

“They are friendly, but it’s not like Peter’s in his inner circle,” a former Trump campaign official said.

“Hey [Thiel] has certainly stepped out more because he feels aligned with Trump and that has made him feel more comfortable in his skin than anything else,” said another former Trump aide.

Boosting Vance

So far, Thiel appears to prefer operating far more behind the scenes than Trump. Throughout the Ohio primary, for instance, he made no effort to dictate how the money he gave to Protect Ohio Values, a super PAC supporting Vance, should be spent — instead entrusting those in charge of the group to spend the nearly $15 million he contributed in whatever ways they saw fit.

Luke Thompson, the executive director of the super PAC, told CNN he has had virtually no interaction with the billionaire benefactor. Given his personal friendship with Vance, Thompson said, Thiel communicated his advice and thoughts directly to the campaign, not Protect Ohio.

But what the super PAC did in public, Thompson said, informed the campaign’s moves in a way that placed Vance in the best position to get Trump’s endorsement — and, subsequently, the nomination.

One 30-second ad that first aired in March began with a voiceover declaring that for Vance, “border security is personal” and ended with a reminder that the candidate has a “personal mission to secure the border.” In between, the ad touts Vance’s Trump-like promises to “finish the wall” and “end welfare for illegals” with an even more Trumpian declaration that “elites and establishment politicians have failed us.”

“At that point, we sort of passed the baton to the campaign,” Thompson said.

Just a few weeks later and right as early voting began on April 5, Vance’s campaign released its first TV ad that hit the exact same message on immigration, with one important distinction: Vance himself appeared in the spot, speaking directly to the camera.

After mockingly asking if Republican voters are “racist” and listing off the problems with illegal drugs and “Democrat voters” coming into the country over the border, Vance pauses and looks down.

“This issue is personal,” he says. “I nearly lost my mother to the poison coming across our border. No child should grow up an orphan.”

That ad, Thompson said, made a bigger impression with voters in focus groups than any of the primary debates. It also delivered enough of a momentum boost for Vance in the polls at the right time to appeal to Trump — at a time when the other Ohio Republican campaigns seemed to have run out of ways to close the deal down at Mar-a-Lago .

“We had him [Vance] tied for first with Gibbons and Mandel going into early voting,” Thompson said. With the new ad and then the Trump endorsement, “he had exit velocity.”

Looking to Arizona

Inside Trump’s orbit, the former President’s allies expect Vance’s come-from-behind victory to result in an endorsement of Masters in the near future. Thiel didn’t convince Trump to endorse Vance, but after the Ohioan’s victory on Tuesday, the former President now believes that the tech mogul has a knack for picking “winners,” according to a person close to Trump.

“I think a Masters endorsement was already happening but JD’s win makes it even more likely,” said the former Trump campaign official, noting that Trump stepped out of a wedding at Mar-a-Lago last Saturday to call into a Masters campaign event.

“I just want to thank you all, you’re an incredible group. I heard Blake was the person that showed up and I want to thank Blake,” Trump said over the phone to the campaign event’s audience, who had gathered to hear about so called election integrity in Arizona.

Trump has already endorsed both Kent and Hageman, who have received contributions from Thiel toward their races. Thiel himself also hosted a fundraiser for Hageman, the Wyoming GOP hopeful who is looking to unseat Rep. Liz Cheney, at his Miami Beach mansion earlier this year that featured Donald Trump Jr. as a guest. At that event, Thiel reportedly told guests he is eager to unseat “the traitorous 10” House Republicans who voted to impeach Trump for inciting an insurrection at the US Capitol on January 6, 2021 (four of whom have since announced their plans to retire) .

But as Thiel has voiced support for helping to rid the GOP of its non-Trumpian members, his actual involvement so far — large contributions to only two candidates and smaller donations to a handful of others — tells a different story. Some Trump allies said they will be closely watching Thiel’s next moves before they get too excited about the prospect of him emerging as a consistent mega-donor on the right.

“I think a lot of people assume [Thiel] is going to be the next Sheldon Adelson or whatever. I’m not so sure of that yet,” said one person close to Trump.

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