Peter Thiel - PayPal

The Strange Politics of Peter Thiel, Trump’s Most Unlikely Supporter
The Republican Party’s new trade-loving, free-thinking, gay, Christian, antiwar, rich-as-hell, naturalized-citizen, Silicon Valley hero.
Max Chafkin & Lizette Chapman
July 21, 2016 — 4:00 AM CDT

When Peter Thiel has the first move in a chess game, he lifts his e2 pawn, the fifth from the left and the one directly in front of his king, and advances it two spaces. It’s an aggressive tactic, putting the bishop and queen into play, which is why Thiel likes it.

The king’s pawn, as it’s known, was the preferred opening by the American chess grandmaster Bobby Fischer. And even though Thiel considers the move more perilous than another popular opening, the queen’s pawn, he’s made it his go-to. “It’s the attacking move,” he explained last year. “If you’re short of world champion level, I always enjoy increasing the risk involved and the volatility of the game.” The comments, made at an event at George Mason University, were revealing. If you’re a few rungs down from the biggest players, he seemed to be saying, it doesn’t hurt to create a bit of chaos.

Thiel boasts a World Chess Federation rating of 2,199, one point short of the group’s lowest honorific, candidate master. At 48, he’s co-founded PayPal, was Facebook’s first outside investor, and is worth almost $3 billion. He still sits on Facebook’s board, and through his firm, Founders Fund, made early bets on Spotify, Airbnb, SpaceX, Lyft, Palantir Technologies, and a half-dozen other private companies worth more than $1 billion each.

His status as ringleader of the PayPal Mafia, the network of former employees and co-founders that includes SpaceX’s Elon Musk and LinkedIn’s Reid Hoffman, makes him one of Silicon Valley’s most influential and admired figures; his iconoclastic politics make him a subject of amusement. Not coincidentally, and disconcertingly to many of those close to him, Thiel is also one of Donald Trump’s most prominent backers.

On Thursday night, after four days of speeches by an eclectic group including the guy who played Chachi on Happy Days, at least one underwear model, and a promoter of professional cage fighting, Thiel is scheduled to address the Republican National Convention in a prime-time speaking slot shortly before Trump accepts the nomination. Thiel declined to comment for this article, but according to a person familiar with his speech, he plans to embrace Trump’s skepticism about recent U.S. wars in the Middle East and to praise the candidate’s economic qualifications—despite Trump’s advocacy of protectionist tariffs and extreme immigration restrictions, measures that would seem at odds with the radical libertarian image Thiel projects. Thiel also plans to say that, though he considers identity politics a distraction, he’s proud of his identity as a gay man.

Thiel’s childhood was filled with signs of quirky genius. He was born in Germany in 1967 and moved to the U.S. at age 1. He was a chess prodigy—ranking seventh in the U.S. Chess Federation’s under-13 age group—with a thing for J.R.R. Tolkien and Ayn Rand. But by the time he made it to college, he was on a very conventional path. The man who urges young people to drop out of college did the full four at Stanford, plus three to earn a law degree. At Stanford, Thiel was a rabble-rouser, but a respectable one. He founded a right-wing newspaper, the Stanford Review, and chose to chronicle the culture wars as a writer, rather than taking up arms himself. The Diversity Myth, a 1995 book he co-wrote with David O. Sacks, railed against multiculturalism, which, they wrote, “exists to destroy Western culture.”

After Stanford came an appeals court clerkship and a job at the white-shoe law firm Sullivan & Cromwell in New York. In a commencement speech at Hamilton College earlier this year, Thiel recalled quitting the firm after seven months and three days. “Looking back at my ambition to become a lawyer, it looks less like a plan for the future and more an alibi for the present,” he said. In the speech, as he usually does, he skipped over the three years he spent at Credit Suisse as a derivatives trader before moving West.

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