In his book The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power, Max Chafkin hones in on college-aged Thiel’s great love of speed chess. At Stanford, Thiel would go to the student union, the Coffee House, and “sit there for hours, playing dozens of consecutive five-minute games, absorbing the lessons of the intense, cerebral sport.”

One day, in Chafkin’s account, Thiel gave some friends a ride to a chess tournament. He drove like a maniac down Route 17, a four-lane highway that crosses the Santa Cruz Mountains, weaving in and out of traffic, flooring the accelerator, and barely avoiding collisions. When the California Highway Patrol finally pulled him over, Thiel told the cop that speed limits are an “infringement on liberty” and quite possibly unconstitutional. The cop decided to let him off with a warning.

In other contexts, his commitment to “liberty” seems to have been a lot more flexible. Some of his classmates at Stanford recalled Thiel, whose family had lived in South Africa in the 1970s, defending apartheid on the basis that “it works” — i.e. that South Africa had a higher level of economic development than its neighbors, rendering irrelevant any moral hand-wringing about the country’s human rights abuses.