Charlie Gray was just 26 when he got his automotive heart broken. Though still young, Gray had a flawless reputation, the right connections—his father had owned a high-end car dealership in Beverly Hills for nearly two decades—and the money, $200,000 of which he’d already plunked down as a deposit. But Porsche was making precisely 918 of their new million-dollar, mid-engine 918 Spyder, and Gray was number 919 on the list. Porsche was prompt in returning his deposit, but for an aspiring predator in the supercar jungle, a six-figure refund is no consolation.

“It was really upsetting,” Gray said, as he sat in the Lodge at Pebble Beach awaiting the Concours d’Elegance, the premier event of Monterey Car Week. “A real bummed-out moment.” Gray, now 36, has one hand tucked inside the chest-baring jacket of his pleated, green Issey Miyake suit; the other is holding a complimentary glass of Billecart-Salmon Rosé he hopes will chase away his hangover. “I know, I know,” he says. “‘Poor little rich boy. You can’t have the Porsche you want.’”