THE HOTTEST TICKET of Monterey’s classic-car weekend in August is an event called, in all seriousness, “The Quail, A Motorsports Gathering.” Hundreds of rare historic cars on emerald-green fairways, gourmet-food tents, corporate sponsors, helicopter rides. In Carmel Valley, Calif., they call it Friday.

It’s also the annual roosting of the species obnoxious millionarus. So there I was, having a chat with Jaguar Land Rover Classic Works director Tim Hannig, when he was accosted by this old blowhard in aviator sunglasses. This...