When Peter Thiel has the first move in a chess game, he lifts his e5 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.