The Winner (3*)

Tennis, the most solo of professional sports, has been Connor O'Toole's ladder to date out of working-class Yonkers.  With the support and old-fashioned-but-wise counsel of a generous mentor who disdains flash, it's already earned him a college scholarship and the knowledge that "he was lucky in the ways that mattered most." We meet Connor during the covid 19 pandemic, shortly after he's graduated from New York Law School with $144,000 in student loans and a widowed, diabetic mother who's just lost her job and her health insurance.  

But things are looking up, at least temporarily:  he's been offered summer lodging in a gated beach community for the one-percent off the coast of Massachusetts in return for giving tennis lessons to the owner of the cottage where he will reside.  John Price, a successful Ivy League lawyer, has sweetened the deal by promising to pitch Connor as a tennis pro (he's not) and help him recruit paying clients from people with the same access code. These include Catherine Havemeyer, a divorced "rentier" as horny as she is demanding.  For readers of my generation, she recalls Mrs. Robinson even before it's revealed she has a lovely daughter, Emily, who aspires to become a (bad) novelist and give away all her mother's money after mom pays her overdue $7,000 monthly rent for an off-season apartment in Brooklyn.

Author Teddy Wayne volleys the tennis metaphor to great effect in articulating what has turned Connor, a self-described "pusher," into The Winner with a chip on his shoulder that's about to get a lot bigger.

In this expensive, gentlemanly sport, Conor had developed a vision of himself as a scrappy grinder who had blazed an unheralded path to success. The rich boys he’d squared off against in college, like the suburbanites he’d played in high school from Bronxville and Scarsdale, were soft and entitled, and if victory didn’t come easily, if they saw they couldn’t close out points within four shots, if they thought they were getting screwed by the umpire, or balls skimming the net kept unluckily dropping on their side, or they were simply worn out from three arduous sets against a guy who hustled to return every goddamn shot and they just wanted to go back to the frat house and pound beers, they either waved a subconscious white flag or very consciously tanked the match (while hurling their $250 racquets in disgust at losing to a fucking pusher from Yonkers).

But it doesn't take much more than his first outdoor shower with a view of the ocean for Connor to fall in love with the fictional Cutter's Neck, and he soon decides that sex with either Havemeyer is more remunerative than sleeping with a townie, after she and her friends join him for a midnight swim at a an absent neighbor's infinity pool that puts him under suspicion for robbery. Connor is neither fish nor fowl at this early stage, but as what first seems to be a juicy romp about class and ethics morphs into a tedious master class in self-justification and cover-up, he definitely becomes the latter.  

It's the new American way in the increasingly amoral Trump era.