Right-wing kingmaker Peter Thiel

Mr. Thiel drew the most attention for two $10 million donations to Senate candidates Blake Masters in Arizona and JD Vance in Ohio. Like Mr. Thiel, the men are tech investors from elite universities who present themselves as antagonists of the establishment. They also worked for the billionaire and depended on him financially. Mr. Masters, the chief operating officer of Thiel Capital, the investor’s family office, has promised to quit that job before Arizona’s August primary.

Mr. Thiel, who declined to comment for this article, announced last week that he would leave the board of directors of Meta, the parent company of Facebook, which conservatives have accused of censorship. One reason for the change: He plans to focus more on politics.

Born in West Germany and raised in South Africa and the San Francisco Bay Area, Mr. Thiel showed his defiant side at Stanford in the late 1980s. His classmates recalled Mr. Thiel, who studied philosophy and law, describing apartheid in South Africa as a sound economic system. (A spokesperson for Mr. Thiel denied supporting apartheid.)

Mr. Thiel also helped found The Stanford Review, a conservative campus newspaper that sought to provide “alternative viewpoints” to what he saw as leftist orthodoxy.

In 1995 he co-wrote a book, “The Diversity Myth”, claiming that the “extreme focus on racism” had caused greater tension and acrimony in society. The rape, he and his co-author, David Sacks, wrote, sometimes included “seductions that are later regretted.” (Mr. Thiel apologized for the book.)

In 1998, Mr. Thiel helped found what would become digital payments company PayPal. He became Facebook’s first outside investor in 2004 and created venture capital firm Founders Fund a year later. Forbes values ​​his fortune at $2.6 billion.

As a venture capitalist, Mr. Thiel presented himself as a maverick. He has published philosophical essays, often dark reflections on politics, technology, Christianity and globalization.

In a 2009 article, Mr. Thiel, who calls himself a libertarian, wrote that he had come to “no longer believe that freedom and democracy are compatible”, arguing that American politics would always be hostile to free-market ideals. and that the policy was to interfere with the lives of others without their consent. Since then, he has hosted and attended events with white nationalists and alt-right figures.

His political gifts evolved with these views. He donated generously to Ron Paul’s presidential campaigns in 2008 and 2012 before turning to more extreme candidates than the Republican establishment.

In 2013, Curtis Yarvin, an entrepreneur who expressed racist beliefs and said democracy was a destructive system of government, emailed Mr. Thiel. Mr. Yarvin wrote that Mr. Cruz, then a newly elected senator, “must purge every traitor” from the Republican Party. In the email, which The Times obtained, Mr. Yarvin argued that it didn’t matter whether these candidates lost the general election or cost Congress control of the party.

Mr. Thiel, who donated to Mr. Cruz’s campaign in 2012, replied: “It’s relatively safe to support Cruz (to me) because he threatens the Republican establishment.”

Mr. Thiel used his money to fund other causes. In 2016 he was revealed as the secret funder of a lawsuit that targeted Gawker Media, which had reported he was gay. Gawker declared bankruptcy, in part because of the costs of fighting the lawsuit.

In July 2016, Mr. Thiel appeared at the Republican National Convention to proclaim he was proud to be a gay Republican supporting Mr. Trump. He then donated $1.25 million to the contestant.

Following Mr. Trump’s victory, Mr. Thiel was named to the president-elect’s executive transition team. During a meeting with technology leaders at Trump Tower in Manhattan in December 2016, Mr. Trump told Mr. Thiel, “You are a very special guy.

A month later, it was revealed that Mr Thiel, a naturalized American, had also been granted New Zealand citizenship. It caused an outcry, especially after Mr Trump urged people to pledge “full allegiance to the United States”.

During Mr. Trump’s presidency, Mr. Thiel grew frustrated with the administration. “There are all these ways things failed,” he told The Times in 2018.

In 2020, he remained on the sidelines. His only notable federal election donation was to Kris Kobach, a Trump ally and former Kansas secretary of state known for his hardline views on immigration. (Mr. Kobach lost his first Senate bid.)

Mr. Thiel’s personal priorities have also changed. In 2016, he announced he was moving from San Francisco to Los Angeles. The following year, he married longtime boyfriend Matt Danzeisen; they have two children.

Mr Thiel scaled back his business commitments and began considering quitting the board of Meta, which he joined in 2005, said two of the people with knowledge of his thinking. At an October event hosted by a conservative tech group in Miami, he alluded to his frustration with Facebook, which was increasingly removing certain types of speech and had banned Mr. Trump.

“I will take on the QAnon and Pizzagate conspiracy theories about a Ministry of Truth any day,” he said.

A spokeswoman for Meta said the company values ​​and has benefited from Mr. Thiel’s contributions.

Mr. Thiel reappeared in political circles. In August, he bought a $13 million mansion in Washington from Wilbur Ross, Mr. Trump’s Commerce Secretary. In October, he spoke at the Federalist Society event at Stanford and at the National Conservatism Conference.

He also rebuilt his relationship with Mr. Trump. Since the 2020 election, they have met at least three times in New York and at Mar-a-Lago, sometimes with Mr. Masters or Mr. Vance. And Mr. Thiel has invested in Mr. McEntee’s company, which builds a dating app for conservatives called RightStuff.

Mr McEntee declined to answer questions about his app and said Mr Thiel was “a great guy”. Representatives for Mr. Trump did not respond to requests for comment.

Mr. Thiel’s political giving intensified last spring with his $10 million checks to PACs supporting Mr. Vance and Mr. Masters. The sums were his largest and single largest contributions ever to a PAC supporting a single candidate, according to OpenSecrets.

Like Mr. Trump in 2016, Mr. Vance and Mr. Masters lack political experience. Mr Vance, the venture capitalist who wrote the best-selling memoir ‘Hillbilly Elegy’, met Mr Thiel a decade ago when the billionaire gave a lecture at Yale Law School, where Mr Vance was a student .

Mr. Vance then worked at Mithril Capital, one of Mr. Thiel’s investment funds, before opening his own fund in Ohio, Narya Capital, in which Mr. Thiel is an investor. Mr. Vance brought in more than $400,000 in salary from Narya in 2020 and the first half of 2021, according to Financial Disclosures.

Mr. Masters met Mr. Thiel when he was a law student at Stanford in 2012 and the investor taught a course on start-ups. The two then co-wrote a bestselling business book, “Zero to One.” In 2020, Mr. Masters brought in more than $1.1 million in Thiel Capital salary and book royalties.

Mr. Vance, Mr. Masters and their campaigns did not respond to requests for comment.

Both candidates repeated the Trumpian voter fraud lie, with Mr. Masters saying in a November campaign ad, “I think Trump won in 2020.” They have also made Mr. Thiel a selling point in their campaigns.

In November, Mr. Vance wrote on Twitter that anyone who donated $10,800 to his campaign could attend a small group dinner with him and Mr. Thiel. Mr. Masters offered the same opportunity for a meal with Mr. Thiel and raised $550,000 selling non-fungible tokensor NFT, from “Zero to One” digital art that would give holders “access to parties with me and Peter”.

Mr. Thiel’s endorsement prompted other tech investors to back both candidates. Mr. Sacks, co-author of “The Diversity Myth” and now an investor, organized a fundraiser for Mr. Vance. Joe Lonsdale, a venture capitalist, held one for Mr. Masters.

Mr. Thiel has also made smaller donations to Trump loyalists, including in September to Ms. Hageman and Patrick Witt, a former Trump administration official running for a House seat in Georgia.

His support may not be enough. In Ohio, Mr. Vance is trailing in the polls, partly hampered by an earlier whistleblowing by Mr. Trump. In Arizona, Mr. Masters competes in a crowded field.

Still, some Republicans worry Mr. Thiel is arming overly extreme candidates with financial firepower, fueling what could be politically damaging primary races.

“You have to nominate candidates who can win in the fall and not just damage everyone along the way,” said Scott Reed, a longtime Republican strategist.

But Mr. Thiel seems ready to move on. In a 20-minute speech to the National Conservatism Conference in October, he said nationalism was “a corrective” to the “brain-dead and unique state” of globalism. He also lambasted the Biden administration.

“We have the retreaded zombies just busy rearranging the lounge chairs,” he said. “We need dissenting voices more than ever.”

Cade Metz contributed report. Rachel Shore and Kitty Bennett contributed to the research.

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