Teddy Wayne is an expert at bringing readers into the minds of young men. While “Kapitoil” and “The Love Song of Jonny Valentine” offered poignant portraits of their first-person narrators, “Loner” took a decidedly dark turn after a bravura opening scene that spotlighted Wayne’s trademark comic skills. “The Winner,” his new novel, mostly leaves humor behind, painting an acid portrait of life in one of America’s privileged gated enclaves and giving us a working-class protagonist who is slowly and thoroughly corrupted by it.
Conor O’Toole is the son of an Irish immigrant construction worker who died when he was 11, raised by his devoted widowed mother. As the story begins, she is recently unemployed and saddled with crippling bills for her diabetes medication. (On the health insurance marketplace plan that replaced her employer’s private insurance, it suddenly costs $672.78 instead of $25, one of the many precise details with which Wayne pinpoints economic inequality.) The year is 2020, and it’s unlikely that anyone will ever again hire his 60-year-old, immune-compromised mother, who is confined at home by the pandemic.
Conor has reluctantly taken a summer gig as a tennis pro in Cutters Neck, “a two-mile pinkie of land jutting out from the southern shores of Massachusetts.” His tennis skills — initially acquired at a neighborhood handball wall with a damaged racquet fished from a garbage can — got him a full college scholarship, but he has $144,000 in law school loans and no job offers after his matriculation from the less-than-prestigious New York Law School.
Teaching tennis lessons is a stopgap while he studies for the bar exam; Conor aspires to steady employment and a middle-class lifestyle along the lines preached by his mentor Richard, a retired lawyer who befriended him and coached his game. A patient, consistent player ultimately has a more secure position than the flashy grandstander who gambles on risky shots, Richard told him: “The sweet spot is being ranked a rung or two below the big shots and not caring about being on top.”
Once Conor gets a glimpse of the life on top of American society, however, it’s not too long before such modest expectations seem paltry. He may roll his eyes at the client who blithely forgets to pay and cringe at the party where no one bothers to wear a mask because, the hostess proclaims, COVID is “a class thing … I don’t even think anyone here will get it.” But when he hits a nearby town bar in search of more compatible company and hooks up with a local named Georgia, he dumps her after a one-night stand. “He was certain that all his hard work was leading him toward a better destination. It was depressingly apparent that Georgia would remain stuck in this town or one like it.”
Georgia, no patsy, responds to the insultingly anodyne kiss-off text wishing her “all the best” with a blunt appraisal: “I bet you think of yourself as a nice guy. But you’re actually an [expletive].” Readers may come to share this assessment as Wayne skillfully leads Conor deeper and deeper into a morass of deception, rationalization, and eventually criminal behavior.
It begins with Catherine Havermeyer, a wealthy older woman who treats him like the help but also aggressively flirts with him on the tennis court and in her absurdly lavish McMansion, where she dangles a check in front of him and makes it clear she will pay for sex. It gets even more complicated when Conor meets Emily, a fragile would-be writer who despite her trust fund has a social conscience and is aware of the unfair advantages she and her peers possess. Conor is in bed with Catherine when he learns that Emily is her daughter. He knows he shouldn’t continue seeing them both, but he’s having the best sex of his life with Catherine, and Emily’s vulnerability brings out his protective instincts. Disaster, unsurprisingly, ensues.
The painful fascination of “The Winner” lies in the fact that Conor knows perfectly well his actions are morally repellent, not to mention extremely risky, but he goes ahead with them anyway. Wayne skillfully orchestrates the whipsaw in his consciousness between reproachful self-knowledge and slimy self-justification. The disconnect becomes increasingly apparent in the novel’s second half, after a violent scene that pivots “The Winner” into thriller territory while continuing to pose uncomfortable ethical questions, for the reader as much as for Conor.
By making his protagonist an average guy thrown in among extremely wealthy people — some nice enough, some nasty, all except Emily thoughtlessly entitled — Wayne invites our sympathy for Conor, then makes us squirm as he becomes less and less likable. Signposts planted throughout indicate that Conor is susceptible to the blandishments of money and power, but it’s still a shock when he dismisses Richard, the man who paid for his tennis equipment, helped him get onto a junior varsity team, and funded his 529 education account, as “a smalltime real estate lawyer … his ironclad code of ethics didn’t apply to this.” The highly ambiguous ending completes our discomfiture.
Class is a subject seldom addressed in contemporary American fiction, perhaps because race and gender have consumed so much of the national discourse. Preceded earlier this year by Adelle Waldman’s excellent “Help Wanted,” Teddy Wayne’s latest makes a welcome contribution to the neglected subject.
THE WINNER
By Teddy Wayne
Harper, 320 pp., $30
Wendy Smith is the author of “Real Life Drama: The Group Theatre and America, 1931-1940.”