Tech billionaire Peter Thiel is searching for new political allies. He’s found one in Kansas.

At his Park Avenue penthouse — 62 floors high and with a sparkling nighttime view of the Manhattan skyline — billionaire Peter Thiel last fall introduced to his friends an immigration hardliner who he would back with over $1 million to try and transform the Republican Party.

The guest of honor was not President Donald Trump. It was Kris Kobach.

Thiel, a California venture capitalist, and Kobach, who is running in Kansas for the Republican nomination for the US Senate, were quite far from Kansas that evening. But the alliance between the two iconoclasts has reshaped the race in that state, giving Kobach a puncher’s chance to beat the GOP establishment — possibly upsetting Republicans’ hopes to hold their Senate majority.

In the months since that fundraiser, Thiel has pumped $850,000 into a super PAC behind Kobach — and that could be just the start if he wins. The investment in Kobach is Thiel’s most significant political bet since he risked his standing in Silicon Valley to support Donald Trump in 2016. And the wisdom of that bet will be tested just next week, when Kobach faces the voters of Kansas in a race that polls show to be tight.

If Kobach is elected, it could give Thiel a loyal ally in the Senate because of how powerful he is proving to be in the race. That alliance becomes all the more key if Trump loses this fall, which would weaken the Washington influence of Thiel, a board member at Facebook and a founder of Palantir, which has deep ties to the government.

Patrick Miller, a political scientist at the University of Kansas who is closely following the primary, told Recode Thiel’s money was “absolutely critical to Kobach being a viable candidate.”

“I don’t want to overstate it and say that Kobach wouldn’t have a campaign without him. But I think the money that that super PAC is putting into the race — primarily through this one rich guy — is absolutely the lifeblood of the pro-Kobach campaign at this moment,” Miller said. “You take that money away and Kobach doesn’t have a lot of campaign left.”

Thiel and Kobach, neither of whom returned requests for comment, are not personally close. Friends of Thiel’s say his support of Kobach hasn’t come up in recent conversations. But Thiel likes to “collect” politicians who he finds well-credentialed and intellectual, particularly those who fight with the elites or the media.

“He has a really strong preference for people who stick their middle finger up to the status quo and conventional wisdom,” said a person familiar with Thiel’s political thinking. “There is nobody who I think was more obviously sticking his middle finger up at conventional wisdom quite like Kris Kobach.”

Both with a zest for the controversial, the litigious, and the troll, Kobach and Thiel have also each collected enemies in their political crusades. They both inveigh against identity politics, the Washington establishment, and a globalism that doesn’t put America first.

Kobach has said Thiel first reached out to him in 2005, which is when Kobach, then a lawyer, began challenging a California state law that gave in-state tuition to undocumented immigrants. A self-professed libertarian, Thiel, who was born overseas and is himself an immigrant, has long had sharply restrictionist views on immigration; back in 2008, he reportedly donated $1 million to NumbersUSA, a hardline immigration group which today is a prominent backer of Kobach’s.

Kobach, as Kansas’s secretary of state from 2011 to 2019, emerged during the ensuing decade as one of the most polarizing figures in national politics, urging the GOP to more seriously investigate voter fraud (of which there is limited evidence) and to crack down on illegal immigration. He had, however, always been seen as a fringe player. That was until Trump arrived.

Kobach has since advised Trump’s administration on implementing a “Muslim registry” that would have specifically tracked immigrants to the US from Muslim-majority countries. He’s also weighed in for the administration on voting issues, was considered for Cabinet posts by a transition committee on which Thiel served, and earned Trump’s endorsement during his unsuccessful bid for governor of Kansas in 2018.

That race was when the Thiel-Kobach bond was tied. Thiel secretly put somewhere between $250,000 and $500,000, delivered in two tranches, into an outside group backing Kobach’s gubernatorial bid, according to a person familiar with the gifts. Some details of Thiel’s stealth donations in that race were previously reported by the Kansas City Star.

For Thiel, the Harvard graduate in Kansas fits in with a new crop of Ivy League-bred, pugilistic Republicans Thiel has cultivated as friends. Despite his proud support for Trump in 2016, Thiel’s influence in Trump’s orbit has faded and he has reportedly soured on the president, not even yet making a donation to his campaign in the 2020 cycle, compared to the over $1 million he spent to back Trump four years ago. Nowadays, Thiel has instead grown closer to rising stars such as Josh Hawley, the Missouri senator who has made a name for himself by fiercely going after Google, which the tech billionaire wants to investigate.

Thiel’s only checks to candidates this cycle have gone to Tom Cotton, another ambitious, Harvard-educated GOP senator, and Kobach. Unlike Hawley, though, Kobach has barely, if ever, weighed in on tech issues.

But part of their alliance can be explained by more personal reasons. A key lubricant binding Thiel to his new candidate is Ann Coulter, the conservative provocateur who last week called Democrats the “antifa party.” She is close with Thiel, and is a Kobach super-fan.

Asked by Recode why she thought Thiel and Kobach felt such a kinship, Coulter took a dig at the GOP establishment and offered that “it might have something to do with Kobach having twice the I.Q. of Mitch McConnell.”

Coulter and Thiel have been fellow rabble-rousers in the conservative movement since at least 2010, when Thiel introduced her to speak to “Homocon,” a conference for gay conservatives held at his apartment. Coulter would even dedicate one of her books to him the following year. The two remain close, attending Hollywood parties together.

It was Coulter who co-hosted that Kobach fundraiser at Thiel’s apartment last fall, an event that brought Kobach before wealthy people like GOP power broker Rebekah Mercer and Erik Prince, the founder of the military contracting firm Blackwater.

“You couldn’t turn around last night without stepping on a billionaire,” Coulter said of the Thiel event in one radio interview.

All that billionaire money has drawbacks, though. While there is a history of rich out-of-staters spending big money to influence Kansas politics, Thiel’s involvement poses a vulnerability.

“Kris’s support comes from those who don’t care about the people of Kansas. He is relying solely on help from Democrats, Hollywood, and New York City,” said Eric Pahls, the campaign manager for Rep. Roger Marshall. Marshall, currently a US representative for Kansas, is the main Republican rival Kobach faces in the primary for the Senate seat.

Thiel made the decision to donate to the super PAC, called Free Forever, after meeting with its leadership in New York last year and hearing a pitch on Kobach’s chances and why the Senate race wouldn’t turn out like the governor’s race, according to a source familiar with the matter. The tech billionaire has no direct decision-making power at the super PAC — he is merely briefed on the ads and other content it produces after it’s made. But Thiel is pleased enough that he’s cut at least three successive checks to the group, the most recent for a half-million dollars last month.

The expectation that Thiel will sink in even more money — rumors swirl in Kansas politics about the precise size of Thiel’s budget — has kept rival campaigns on their toes.

The super PAC Thiel is backing has spent more than four times what Kobach’s campaign itself has spent on television and radio ads, according to data shared with Recode by the media tracking firm Medium Buying. The heavy amount of mailers sent by the PAC have run the gamut of attacking Marshall as “anti-American” for being insufficiently tough on immigration, alleging that he voted to fund “Rosie O’Donnell summer camp,” “global warming musicals,” and “transgender plays,” and promising that Kobach will “stop the next Ruth Bader Ginsburg.” Thiel may not be making decisions, but the messaging feels Thiel-esque.

If Kobach wins next week, he’ll have a tough general election on his hands, too. Even more Thiel money would almost certainly be needed.

And if Thiel does donate more in the fall, he will likely end up spending more money on Kobach’s behalf than he had on behalf of his previous bet: Trump.