Mr. Thiel has attracted the most attention for two $10 million donations to the Senate candidates Blake Masters in Arizona and JD Vance in Ohio. Like Mr. Thiel, the men are tech investors with pedigrees from elite universities who cast themselves as antagonists to the establishment. They have also worked for the billionaire and have been financially dependent on him. Mr. Masters, the chief operating officer of Thiel Capital, the investor’s family office, has promised to leave 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 Meta, the parent company of Facebook, which conservatives have accused of censorship. One reason for the change: He plans to focus more on politics.
A Moneyman’s Evolution
Born in West Germany and raised in South Africa and the San Francisco Bay Area, Mr. Thiel showed his provocative side at Stanford in the late 1980s. Classmates recalled Mr. Thiel, who studied philosophy and law, describing South Africa’s apartheid as a sound economic system. (A spokesman for Mr. Thiel has denied that he supported apartheid.)
Mr. Thiel also helped found The Stanford Review, a conservative campus paper that sought to provide “alternative views” to what he deemed left-wing orthod.
In 1995, he co-wrote a book, “The Diversity Myth,” arguing that “the extreme focus on racism” had caused greater societal tension and acrimony. Rape, he and his co-author, David Sacks, wrote, sometimes included “seductions that are later regretted.” (Mr. Thiel has apologized for the book.)
In 1998, Mr. Thiel helped create what would become the digital payments company PayPal. He became Facebook’s first outside investor in 2004 and established the venture capital firm Founders Fund a year later. Forbes puts his fortune at $2.6 billion.
As a venture capitalist, Mr. Thiel branded himself as a contrarian. He published philosophical essays, often dark musings on politics, technology, Christianity and globalization.
In one 2009 piece, Mr. Thiel, who called 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 politics was about interfering with other people’s lives without their consent. Since then, he has hosted and attended events with white nationalists and alt-right figures.
His political giving evolved with those views. He donated lavishly to Ron Paul’s 2008 and 2012 presidential campaigns before turning into candidates who were more extreme than the Republican establishment.
In 2013, Curtis Yarvin, an entrepreneur who has voiced 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, “needs to purge every single traitor” from the Republican Party. In the email, which The Times obtained, Mr. Yarvin argued that it didn’t matter if those candidates lost general elections or cost the party control in Congress.
Mr. Thiel, who had donated to Mr. Cruz’s 2012 campaign, replied, “It’s relatively safe to support Cruz (for 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, partly from the costs of fighting the lawsuit.
In July 2016, Mr. Thiel appeared at the Republican National Convention to proclaim that he was proud to be a gay Republican supporting Mr. Trump. He later donated $1.25 million to the candidate.
After Mr. Trump won, Mr. Thiel was named to the president-elect’s executive transition team. At a meeting with tech leaders at Trump Tower in Manhattan in December 2016, Mr. Trump told Mr. Thiel, “You’re a very special guy.”
A month later, Mr. Thiel, a naturalized American, was revealed to have also obtained citizenship in New Zealand. That prompted a furor, especially after Mr. Trump had urged people to pledge “total allegiance to the United States.”
During Mr. Trump’s presidency, Mr. Thiel became frustrated with the administration. “There are all these ways that things have fallen short,” he told The Times in 2018.
In 2020, he stayed on the sidelines. His only notable federal election donation was to Kris Kobach, a Trump ally and former secretary of state of Kansas known for his hard-line views on immigration. (Mr. Kobach lost his primary bid for the Senate.)
Mr. Thiel’s personal priorities also changed. In 2016, he announced that he was moving from San Francisco to Los Angeles. The next year, he married a longtime boyfriend, Matt Danzeisen; they have two children.
Mr. Thiel reduced his business commitments and started pondering leaving Meta’s board, which he had joined in 2005, two of the people with knowledge of his thinking said. At an October event held by a tech group in Miami, he alluded with frustration with Facebook, which was his conservative removing certain kinds of speech and barred Mr. Trump.
“I will take QAnon and Pizzagate conspiracy theories any day over a Ministry of Truth,” he said.
A Meta spokeswoman said the company valued and had 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 trade secretary. In October, he spoke at the event for the Federalist Society 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 invested in Mr. McEntee’s company, which is building a dating app for conservatives called the RightStuff.
Mr. McEntee declined to answer questions about his app and said Mr. Thiel was “a great guy.” Mr. Trump’s representatives did not respond to requests for comment.
Giving to Win
Mr. Thiel’s political giving ramped up last spring with his $10 million checks to PACs supporting Mr. Vance and Mr. Masters. The sums were his biggest and the largest ever one-time contributions to a PAC backing a single candidate, according to OpenSecrets.
Like Mr. Trump in 2016, Mr. Vance and Mr. Masters lack experience in politics. Mr. Vance, the venture capitalist who wrote the best-selling memoir “Hillbilly Elegy,” met Mr. Thiel a decade ago when the billionaire delivered a lecture at Yale Law School, where Mr. Vance was a student.
Mr. Vance later 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 took home 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 Stanford law student in 2012 and the investor taught a class on start-ups. The two later co-wrote a best-selling business book, “Zero to One.” In 2020, Mr. Masters reported more than $1.1 million in salary from Thiel Capital and book royalties.
Mr. Vance, Mr. Masters and their campaigns did not respond to requests for comment.
Both candidates have repeated the Trumpian lie of election fraud, with Mr. Masters statement 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 by selling nonfungible tokensor NFTs, of “Zero to One” digital art that would give holders “access to parties with me and Peter.”
Mr. Thiel’s backing has prompted other tech investors to support the two candidates. Mr. Sacks, the co-author of “The Diversity Myth” and now an investor, hosted a fund-raiser 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 backing may not be enough. In Ohio, Mr. Vance trails in polling, partly hampered by a previous denunciation of Mr. Trump. In Arizona, Mr. Masters is competing in a crowded field.
Still, some Republicans worry that Mr. Thiel is arming candidates who are too extreme with financial firepower, fueling what could be politically detrimental primary races.
“You have to nominate candidates who can win in the fall and not just damage everyone on the way,” said Scott Reed, a longtime Republican strategist.
But Mr. Thiel appears ready to press forward. In a 20-minute speech at the National Conservatism Conference in October, he said nationalism was “a corrective” to the “brain-dead, one-world state” of globalism. He also blasted the Biden administration.
“We have the zombie retreads just busy rearranging the deck chairs,” he said. “We need dissident voices more than ever.”
Cade Metz contributed reporting. Rachel Shorey and Kitty Bennett contributed research.