When you think of tech billionaires and their cars, visions of Teslas, McLarens, and the latest Ferrari hypercars usually come to mind. But Peter Thiel—the PayPal co-founder, Facebook backer, and Silicon Valley contrarian—doesn’t always play by the script. True to his reputation for zigging when others zag, Thiel’s garage is a fascinating mix of practical choices, oddball indulgences, and left-field collector’s items that hint at a mind constantly probing the edges of convention.