The Winner by Teddy Wayne

Teddy Wayne's "The Winner" introduces Conor, an ambitious law graduate from an obscure institution who's determined to prove his worth in a competitive legal world. 

Without any job prospects and needing to support his chronically ill mother, he takes a summer job teaching tennis at the affluent gated community of Cutters Neck, Massachusetts. One of his first students is Catherine, a magnetic divorcée keen to hire him for more than advice on her serve.

What begins as a transactional arrangement soon develops into an intoxicating sexual relationship. Things become even more complicated when Conor encounters Emily, with whom he has his first taste of real intimacy. Against his better judgment, he soon finds himself living a double life that inevitably leads to disaster.

Conor knows how hard it is to win against those with money and power. In his fight for survival, he has to put emotion aside and play with only his wits – after all, in tennis, love means nothing.