Thiel sat on President Trump’s executive transition team; Palantir, Thiel’s data analytics firm, procured a number of lucrative government contracts. Behind the scenes, Chafkin says, Thiel was pushing for a “Republican crackdown on tech companies,” and more specifically on Google, his nemesis. (Google’s size and reach presented, in Chafkin’s words, “a threat to nearly every company in Thiel’s portfolio.”) You might think that this deployment of government power would go against everything the libertarian Thiel believed in, but you begin to wonder, while reading “The Contrarian,” whether the Big Government bullying that conservatives warned against before Trump became president was in fact just a projection of the big-footing they would gladly do if given the chance — Trumpism as a form of wish fulfillment. In Chafkin’s summary: “Get on the Trump train, or get a visit from the F.T.C.”

Credit…Caroline Tompkins

As it happens, Thiel was bullied as a child — a skinny, socially awkward, chess-playing boy, he protected himself by becoming resolutely “disdainful.” He was born in Germany and moved to the United States as an infant, in 1968. His father’s job at an engineering firm also meant a sojourn in apartheid South Africa, where the younger Thiel attended an elite, all-white prep school. He went to Stanford and started the Stanford Review, a conservative newspaper, staying put to go to law school. An unsatisfying stint as a corporate lawyer ended when he failed to get the Supreme Court clerkship he so desperately wanted. “I was devastated,” Thiel would later recall, saying it precipitated a “quarter-life crisis.”

“The Contrarian” recounts Thiel’s professional trajectory in full, depicting him stumbling into the tech industry not out of any particular passion but because it presented an opportunity to get rich. Thiel, unlike the fantasy of the American entrepreneur who risks it all for his dream, was always hedging his bets — even, at one point, proposing that PayPal turn over its limited cash reserves to his own hedge fund so that he could speculate with the money.

Chafkin portrays Thiel’s support for Trump on the 2016 campaign trail in similar terms. Chances are, any establishment Republican would have been fine for Thiel’s business interests, and Thiel had already scandalized Silicon Valley with his criticisms of women’s suffrage and immigration. But if Trump won, Thiel was bound to be rewarded by a president who clearly prized demonstrations of loyalty above all else. Not to mention that Thiel — by any material measure a master of the universe — relished the thought of Trump sticking it to that part of the elite club that wouldn’t have him as a member. As one of Thiel’s investors put it, “He wanted to watch Rome burn.”

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