THE WINNER, by Teddy Wayne
Emily, one of three women in Teddy Wayne’s seductive sixth novel, “The Winner,” to sleep with Conor O’Toole during his summer as tennis pro in an exclusive gated community near Cape Cod, tells him he’s conventionally handsome — like a political candidate running for office mostly because he looks the part. Or, she says, “someone on a dating show who, I don’t know, sells condos in Florida, and likes jet-skiing, and uses the word badass.”
Someone less pretty, she implies, might actually have had time to develop an interior life. “And you think I’m the kind of person who gets whatever he wants without trying?” Conor asks. “Yes,” she replies. “You’re clearly a … winner.”
While Conor may be able to rely on the currency of his good looks, he probably wouldn’t agree with Emily. He arrives in the fictional hamlet of Cutters Neck in the summer of 2020, fresh out of a second-tier law school with $144,000 in student loan debt and no job prospects. His father died when he was young and his mother, recently laid off as a receptionist, barely makes enough in unemployment to keep their Yonkers rental. Even his extraordinary work ethic is no guarantee.
It was only through the good graces of a long-ago mentor — a kindly retired attorney who spotted him as a lonely eighth grader hitting a ball against a wall with an abandoned racket — that Conor developed the skills that earned him a college scholarship and ultimately led to this summer job, giving a wealthy man lessons. In exchange, he gets to live free in the man’s guesthouse and gain access to other rich people who might want to work on their backhands.
The chip on Conor’s shoulder is class-based, a narrative specialty of Wayne’s, and one heightened here by the contrast between the Covid-19 pandemic’s haves and have-nots. Conor’s mom is a Type 1 diabetic, and he needs every cent he makes to keep her on insulin. His plan is to hole up when he’s not on the court and study for the bar exam, but between various eager women and his own libido (highly muscular), the summer gets complicated.
One of his tennis pupils is the glamorous but chilly Catherine Havemeyer, who has the biggest house on Cutters Neck, a place populated almost exclusively by people with inherited wealth. She pays extra to give Conor lessons in intense sexual gratification.
And: She’s Emily’s mother. This is “The Graduate” with an advanced degree.
Wayne’s plot was made to gallop, and it does not disappoint. I read “The Winner” in two nights. It’s not just the sex that’s provocative; it’s the way the reader is steadily pulled into Conor’s dilemma — with Emily he genuinely feels romantic love for the first time, but the woman who turns him on is Catherine — to the point that some of his actions seem almost justifiable. It takes a long time narratively to root against him at all.
In contrast, souring on the physically unblessed protagonist of Wayne’s 2016 novel “Loner” was easy. The similarities between them abound: That book’s subject, David Federman, is a Harvard freshman with a chip on his shoulder, a disconnect from most emotions (except envy) and a crush on a classmate, a private school goddess not unlike Emily.
“Loner” read as an exceptionally creepy portrait of male entitlement and the toxicity of the male gaze. “The Winner” feels in many ways like the same story, but delivered in a more consistently fun package. Do we cut the emotionally inert but good-looking guy more slack because he frets about money and his diabetic mother, and is himself intensely subject to objectification? I’d judge Wayne on his easy access to the immoral and amoral, but given my own voracious consumption of this book, better to stay off my high horse.
THE WINNER | By Teddy Wayne | Harper | 309 pp. | $30
