Mr. Thiel has attracted the most attention for two $10 million donations to the Senate candidates Blake Masters in Arizona and J.D. 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 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 orthodoxy.
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.
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 to 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.
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 conservative tech group in Miami, he alluded to his frustration with Facebook, which was increasingly removing certain kinds of speech and had barred Mr. Trump.