Empathizing with the Antihero in “The Winner”

Some people have all the luck. Usually the luckiest people are attractive, white men, much like the protagonist of Teddy’s Wayne’s latest novel, The Winner. Wayne has built his career by crafting unlikable male protagonists and wielding a sharply honed narrative voice, and these skills culminate in The Winner.

In the first pandemic summer of 2020, Conor O’Toole has just finished law school. His plans include studying for the bar, finding a law firm job, and teaching tennis. He’s negotiated his way into a private beach enclave on a spit of land just south of Cape Cod. In exchange for tennis lessons, a wealthy lawyer offered him use of a cottage. On Cutter’s Neck, the rich homeowners have fled the dangers of COVID and are isolating themselves by attending outdoor cocktail parties and only swimming at the private pool. The setup is typical of Teddy Wayne’s five other novels. Privilege becomes fodder for examination by a protagonist who ultimately reveals himself as unworthy. 

When we first meet Conor, he’s introduced as a handsome, likable working-class kid. He’s a sympathetic, relatable character who has had a hard life, with a father who’s committed suicide and a diabetic mother whose insulin Conor is responsible for. And with COVID a particular danger to diabetics, Conor constantly worries his absence from her life makes her vulnerable. He’s a mama’s boy, calling her regularly, further endearing him to the reader. But, as with all of Wayne’s characters, it isn’t long before we realize Conor is a deplorable person.

Wayne excels at creating rich characters who readers empathize with and can relate to. They are everyman-archetypes, if everyman was rotten to the core. And even as they reveal themselves, their flaws spill out slowly enough to seem minor and forgivable. His portraits are whole. Conor, for instance, sleeps with a woman from town, a local townie, but by morning, informs her he’s not interested in anything serious, or probably even in seeing her again. He’s unkind, but also relatable. Revealing these minor offenses sets us up to accept the bigger tragedies. 

The success of The Winner stems from the effort Wayne put into retaining the reader’s sympathy for the protagonist, even long after his descent into despicability. And in Conor, Wayne has crafted his greatest villain to date. The narrative evolves into a page-turning suspense thriller, something of a departure from the slower pace of Wayne’s other novels. Be warned, there are inevitable spoilers from this point on. 

Conor’s objective during the summer months, besides studying for the bar, is offering paid lessons to the other residents of Cutter’s Neck. His desperation for cash is a huge motivation. Even if he is buying his mother’s insulin, the constant reminder of his poverty is another of Conor’s minor flaws. He wants money for good reasons, but he’s quick to remind us of it. 

His financial needs land him in bed, literally, with Catherine, one of the wealthiest homeowners on Cutter’s Neck. She’s more than twice his age, but willing to pay three times his usual rate for her private, bedside lessons. Conor takes pleasure in their sessions too, even after he unwittingly falls for Catherine’s daughter Emily. The lover’s triangle seems a bit predictable, at least until Conor ends up murdering Catherine. 

There are similarities here to the plot of Wayne’s 2017 novel, The Loner, where the protagonist seduces the roommate of his love interest, setting up another kind of love triangle. Love triangles are meaty romance plots with plenty of space for secret-keeping. In that novel though, David’s assault and rape of the women means he’s unredeemable. The reader doesn’t hope David can escape unscathed. But for Conor, Wayne has skillfully created a deplorable character, a literal murderer, but one who the reader can still side with. The excitement and empathy Wayne creates for Conor increases the suspense of the final chapters of The Winner. 

There are plenty of reasons to dislike Conor. He mistreats women, and not just the townie he has a one-night stand with or the woman he murders. He’s a classic ‘nice guy,’ and actually very similar to the protagonist in The Loner. For instance, Conor “regarded female pleasure as a goal worth pursuing as much for his own psychological well-being as for her satisfaction; unlike most men, he would rather forgo his climax if it meant guaranteeing his partner’s.” Sure, Conor just wants his partner to get off and he wants us to believe he’d sacrifice his own orgasm. We might just believe that too if, a few pages later, he was more supportive of Emily’s ambition as a writer. 

Emily has written a novel. It’s a not-very-good satire of the rich people on Cutter’s Neck. Conor reads the book and dislikes it, causing him to consider how “At the outset of their relationship, he couldn’t have imagined he’d care whether her novel was any good. But now he wished she’d give it up and find something practical to do with her life.”  We’re expected to believe he wants her to orgasm, but also wants for her to find a more useful pursuit than writing despite it bringing her pleasure. Conor eventually betrays to us who he really is: “Emily was the long-haul in-vestment.” 

Despite these flaws, the reader still finds enough to like about him to be caught up hoping he escapes, probably for similar reasons why audiences respond to Tom Ripley in Patricia Highsmith’s novels. Conor O’Toole is an enticing anti-hero. The residents of Cutter’s Neck are the wealthy elite. They are gross in their consumption and treatment of people, resented by the locals and us as the readers. Conor, the working-man hero is simply trying to fit in with the  society he aspires to. 

There are plenty of other ways Wayne plays with class in the novel too. When a house is broken into on Cutter’s Neck, Conor immediately suspects a local town resident. His assumption turns out to be false when Emily reveals it was one of the many misanthropic rich kids who live there. The wealthy boy faces no consequences. It does feel a bit of a forced plot device, but one that illustrates how Conor quickly becomes one of ‘them,’ shifting from the perspective of an outsider, to one of those who belong in the privileged society. 

Wealth is under investigation here too. Emily, the spoiled rich girl, aspires to write thinly veiled fiction. She’s awful at it, but wealth insulates her from that limitation. Conor, who sees Emily as a meal ticket, knows he can’t tell her how bad it is without consequences. In the end, he slips into the role of wealthy society member easily. He’s a winner. 

There are moments in the narrative where procedural elements slow down the pacing, and Conor probably should have spent another year or two in law school. But these are relatively minor quibbles. Wayne has packaged a literary examination of wealth and privilege as a summer thriller. We should feel shame for allowing Wayne to manipulate us into sympathizing with Conor O’Toole, but our failure speaks to the strength of his writing. The Winner delivers another scathing indictment of human nature, even if that means indicting ourselves. 

FICTION
The Winner
By Teddy Wayne
Harper
Published May 28, 2024