Demimonde Dreaming

Had Jay Gatsby gunned his yellow Rolls-Royce between Manhattan and Long Island’s North Shore a few decades later, he might, in essence, have crossed paths with a young Guy Trebay.

Like Gatsby, Trebay’s family occupied a sprawling mansion. They drove a series of luxury-model cars. Like Gatsby, Trebay’s tall, handsome father made a fortune befitting his era, with a cheesy men’s cologne called Hawaiian Surf that, the future writer started to notice, involved sales trips with a pretty secretary in tow. While Trebay and his siblings made like rich little hippies—drugs, beach bonfires, and petty theft—their parents partied hard and lived perilously, the Pall Malls that would eventually kill his glamorous, daredevil mother never far from her side.