"Be prepared to fully lose yourself in The Winner--a book I started and then simply couldn't stop reading. Teddy Wayne has written a timely, topical novel that still somehow feels like a classic."--Liz Moore, New York Times bestselling author of Long Bright River

Conor O'Toole has never been anywhere as casually glamorous as Cutters Neck, a gated community near Cape Cod. It's a sweet deal for the summer: free lodging in a guest cottage in exchange for tennis lessons, luxuriously 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. Then a sharp-tongued divorcée appears, offering him double his usual rate. Soon he realizes Catherine 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 the artsy, outspoken girl he met on the beach. Conor somehow finds a way to manage 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.