Naked, Then Dead

On Teddy Wayne's "The Winner"

This review essay first appeared in The Mars Review of Books

Twenty-five year-old Conor O’Toole, fresh out of New York Law School—not New York University Law School—is spending the first summer of the pandemic on Cape Cod, giving tennis lessons to the one percent. He is a working class kid, out of Yonkers, with a dead father and an ill mother laid off from her secretarial job. Thanks to the generosity of a white shoe lawyer who wants to play better tennis, Conor has his own guesthouse, and he’s grateful for the teaching income and the time to study for the bar. He’s grateful, too, to escape the terror and the slog of COVID-era New York. The rich, he learns, play by their own rules.

There’s an extraordinarily wealthy divorcee, Catherine, who takes lessons from Conor—except she’s not interested in bettering her game, only her sex life, and a chiseled, mid-twenties ex–college athlete will do. For larger sums of money than he’d earn teaching tennis, Conor has sex with her, and finds he enjoys it greatly, cash or no cash, even as Catherine, cool and cutthroat, grows ever more demanding. To make matters thornier, Conor’s falling for an artsy Barnard grad named Emily who reveals, as their courtship deepens, that Catherine is her mother. Neurotic Emily can’t match her mother’s mind-blowing libido, but she and Conor plainly gel, and as an heiress to a vast fortune—Catherine’s house in the fictional coastal town of Cutters Neck is worth $26 million—she might just be his ticket out of drudgery.

Catherine, as one can imagine, will not be easily dumped.

This is the premise of Teddy Wayne’s propulsive, winning, and occasionally frustrating new novel, The Winner, which arrives as something of the male counterpoint to last year’s summer sensation, The Guest. Emma Cline’s novel, about a young twenty-something hoping to trade on her looks in the Hamptons to get back in the good graces of her much wealthier and older ex—while dodging a dangerous drug-dealer back in the city—is, like The Winner, an elegant distillation of modern social dynamics, the incredibly affluent bubbling themselves in oceanfront manses as the help and the townies churn just out of reach. Conor is an uneasy witness, an insider-outsider, popping up at the cocktail parties and bobbing in their surf, passing, in part, because he is good-looking.

Wayne, who writes on male alienation as well as any contemporary American novelist, has chosen for himself a superficially different protagonist than those of his prior books, including Loner, which made the daring decision to inhabit the consciousness of a furious proto-incel at Harvard. While Loner’s David Federman is a nebbish beta who longs for alpha-hood, Conor is there already. He was a tournament tennis player in high school and starred at an unnamed D-II college, and Wayne tells us, through a close third person narration, that Conor has slept with numerous girls throughout his young life. Until Catherine and Emily arrive, his habit has been to take them in reluctantly, like an ennui-laden movie star. He’s only had one serious girlfriend and aspires to more meaningful connections.

But Conor, like Federman, is possessed of an outsider’s fury, though his comes at a slower burn. He resents the ease and decadence of the rich; even lovely Emily, with her ability to use her trust fund to pay rent, quietly roils him. Emily wants to be a novelist and shows him a draft of a work about a girl much like herself. “The central problem Emily herself alluded to—that no one was interested in or sympathetic to how an excess of money had poisoned a rich white girl’s family—was inescapable.” Conor finds, by the end of two hundred and forty “excruciating” pages, that he “despised the teenage Alice. She was spoiled, oversensitive to any slight, the constant victim in her own mind of her absent, apathetic father and monstrously narcissistic mother.”

Hypocrisy grates Conor. By setting The Winner in 2020, Wayne is able to slyly lampoon the excesses of that summer, the obscenely rich throwing up Black Lives Matter signs and fretting over diversity trainings, the COVID hawks dropping all precautions if they find themselves at the right parties. Conor is worried about COVID until, with enough sunshine on the Cape, he’s not. “He supposed this was what normal life was like for people this rich: so removed from the ravages of the world that to be concerned by them would be like fretting over natural disasters on Mars.” His resentments are buried within; he wants to be in this world, after all, and he’s got $144,000 in law school debt to pay off. Conor’s style of tennis is emblematic of who he is, since he’s known, on the court, for his mental toughness and inability to give up on a rally. Pejoratively, he’s a pusher, but pushers can overcome more talented opponents by forcing them to make mistakes. Conor is fastidious, and he won’t be broken.

Wayne allows us to ponder what makes privilege: class, gender, race, or physique. The novel’s title comes from a pronouncement Emily makes when she dismisses Conor as a “winner,” the type of person who lacks an “interior life” and is “used to getting whatever they want without even trying.” He is not, in Emily’s view, a “funny, charming, self-loathing loser,” her usual type. There is, of course, a deep absurdity to a generational millionaire telling the son of a single diabetic mom from Yonkers that he can have whatever he wants without any effort. Emily has her own demons—we learn she spent time in a mental institution—but she will die as she was born: very, very rich. Whether she is aware of it or not, she wields extraordinary power.

But Conor, effortlessly dashing, can blend better than the more homely members of his class. He can play the part in Cape Cod. He insists, throughout the summer, he can never get a job at the law firm where his host, the man who wants to bolster his tennis game, works, since he is not a graduate of an elite law school, one Conor’s Cape acquaintances keep confusing with NYU. But lo and behold, Conor is offered a Zoom interview that is not pro forma—he gets another, and he finds his tenacity is rewarded. The corporate attorneys like what he says. Gone unsaid, but perhaps implied, is they like how he looks. David Federman could not make a go on the Cape, simultaneously shtupping a shapely mother and daughter. Conor is too hot to be a loser.

The Winner accelerates when Catherine decides to out Conor to Emily. Conor goes to extreme lengths to ensure this does not happen. Wayne is deft when it comes to making Conor’s radical actions—and his budding psychopathy—plausible. (To reveal what Conor does in the end would be a profound spoiler.) From a remove, Conor’s rationalizations are terrifying, but up close, with Wayne nudging us along, we can find the horror almost alluring, rooting for Conor, hustler that he is, to survive the jeopardy he has manifested for himself. If he was, as a poor boy drowning in law school debt and his mother’s insulin bills, a victim of Catherine’s predation—as much as he loved the sex, he was a glorified prostitute—he long transcends that status by novel’s end.

If The Winner’s pace never slackens, the prose sometimes does. Certain imagery is tangled (“July’s blinding glare slanted into the coppery haze of August”) and there are instances of Wayne straining too hard to emphasize what we know well enough—there are glaring class disparities. “Their money was a kind of vaccine,” Wayne intones. Or, when we’re deeper into Conor’s unraveling: “It was hard to miss this suggestion that a rich person’s life was considered worthier of law enforcement protection.” And another: “Already it had become clear that the pandemic’s worst comorbidity was poverty . . . .” In actuality, it was age.

And The Winner suffers from an ending that is simultaneously too open-ended and pat, and seemingly truncated, as if Wayne were in a hurry to slam the door on Conor and Emily. Clocking in at just over three hundred pages, the novel could have had more time to resolve itself, perhaps even to trail Conor beyond Cutters Neck. In that sense, it stumbles like The Guest, which was elevated by its gem-cut prose but faltered at the very end, never cohering as it should. This is a growing problem with newer novels published by major conglomerates; many of these imprints seem afraid of passing some arbitrary page count, lest attention spans are challenged or extra cash is dumped on paper. It is to Wayne’s credit the reader is left wanting more from The Winner. How does Conor, his social station elevated, adjust to life in tony Manhattan? Or, more simply, how does he truly outrun his lurid past? What happens when 2020 passes? Given another hundred pages, Wayne could have sketched a richer portrait of winners and losers, and those so desperate for the good life that they’ll succumb to depravity to keep tasting it.