The Winner, a propulsive literary thriller from Whiting Award winner Teddy Wayne, delves into the life of Conor O'Toole, a young law student who finds himself teaching tennis in a posh gated community near Cape Cod. Amid the casually glamorous surroundings of Cutters Neck, Conor is living in a guest cottage, a world away from the cramped Yonkers apartment he shares with his diabetic mother.

Despite being surrounded by oceanfront luxury, Conor and his mother have bills to pay, and attracting new clients for tennis lessons is harder than he anticipated. That's until he crosses paths with a sharp-tongued divorcée named Catherine, who offers to pay him double his rate, with the expectation of some additional, more intimate services.

As Conor becomes entangled in a secret, erotic affair, he also finds himself romantically drawn to a quirky, outspoken girl he met on the beach—who happens to be Catherine's daughter. Caught in a tangled web of desire and deception, Conor believes he's found a way to balance everything, until he makes a disastrous, irreversible mistake. This darkly comedic thriller skewers the elite with wit and delivers an unputdownable, cinematic, and psychologically astute narrative.