The Winner

Conor O'Toole, a working-class law school graduate from Yonkers, lands a summer job teaching tennis in Cutters Neck, an exclusive gated community near Cape Cod. In exchange for lessons, he gets free lodging in a luxury cottage, but he soon finds himself desperate for cash to support his sick mother.

When a wealthy older divorcée offers him double his rate for off-the-court companionship, Conor enters a secret, lucrative affair while simultaneously falling for a young woman on the beach. As he struggles to balance both relationships and hide his double life, one critical misstep threatens to destroy everything.