Four years ago, billionaire venture capitalist and Facebook board member Peter Thiel made one of his biggest bets: He went all in on Donald Trump. The normally tight-lipped and enigmatic Thiel gave a very public imprimatur as a prominent speaker at the Republican convention, tying his reputation as one of the most successful figures in modern tech to a presidential candidate despised throughout Silicon Valley.
“Tonight,” he said in a nationally televised address at the convention, “I urge all of my fellow Americans to stand up and vote for Donald Trump.” He made history as the convention’s first speaker to declare himself “proud to be gay” and he extolled Trump not as “a return to the past” but rather a return to “that bright future.”
Thiel was used to making risky bets. He was a startup veteran, a PayPal cofounder who wrote Facebook a check for $500,000 months after it launched. But Trump was different. Few in Silicon Valley wanted in on that round. Still, just a week after the Access Hollywood tape leaked of Trump boasting about sexually assaulting women — a clip that sent other prominent Republicans fleeing — Thiel ponied up $1.25 million.
The donation was well known. But what has not been previously reported is just how much Thiel was willing to gamble on Trump’s MAGA movement during the 2016 election. His bet went far beyond money, speeches, or even mainstream Republican politics. Even as Thiel staked his reputation on the candidate in public, he met in private with the racist fringe that felt emboldened by Trump’s rise to power. [Continue reading…]