“Seductive…consistently fun…This is The Graduate with an advanced degree. Wayne’s plot was made to gallop, and it does not disappoint. I read The Winner in two nights. It’s not just the sex that’s provocative; it’s the way the reader is steadily pulled into Conor’s dilemma…I’d judge Wayne on his easy access to the immoral and amoral, but given my own voracious consumption of this book, better to stay off my high horse.”—The New York Times

Conor O’Toole has never been anywhere like Cutters Neck, a gated community near Cape Cod. It’s a sweet deal for the summer: in exchange for tennis lessons, he receives free lodging in a luxurious guest cottage, far from the cramped Yonkers apartment he shares with his diabetic mother.

In this oceanfront paradise, however, new clients prove hard to come by, and Conor has bills to pay. When Catherine, a sharp-tongued divorcée, offers double his usual rate, he soon realizes she is expecting additional, off the court services for her money, and Conor tumbles into a secret erotic affair unlike anything he’s experienced before.

Despite his steamy flings with a woman twice his age, he simultaneously finds himself falling for an artsy, outspoken girl he meets on the beach. With cautious, strategic planning, Conor somehow manages this tangled web—until he makes one final, irreversible mistake.

A dark, explosive literary thriller that brilliantly skewers the elite, Whiting Award winner Teddy Wayne’s unputdownable novel is cinematic, shocking, and a psychological masterpiece.