Tennis Triangles and Dark Twists: A Review of Teddy Wayne’s “The Winner”

"The Winner"

Teddy Wayne drops two clues in his novel The Winner’s epigraphs.  First, “A little water clears us of this deed” from Macbeth. A sinister sign for what’s ahead. And then, from Allen Fox’s Think to Win: The Strategic Dimension of Tennis, “The true defensive player (or ‘dinker,’ as he is unaffectionately called in recreational circles) is prepared to hit ten, twenty, or more balls in the court per point…Dinkers understand the facts of life at the recreational level of tennis.” Both choices shed light on the narrative arc: dark, bloody waters ahead and defensive court volleys to score recreational points in a game. That’s our direction in this novel. The Winner transports us into wealthy, elitist Wasp America, and it sets up its social satire through tennis lessons and dark relationship triangles of sex, violence, lies, and concealment.  It’s an entertaining, and darkly brutal twisting of the “rags to riches” tale, as it pokes at the dark heart of the American story of success at all costs.  

At the core of this novel is Conor O’Toole, who heads to the gated community of Cutters Neck, near Cape Cod, in order to serve John Price and the other wealthy neighbors there as a tennis instructor. He’s recently finished law school at New York Law School (not NYU), is saddled with $144,000 in debt, and caring for his diabetic mother in a small Yonkers apartment.  Conor is juggling his own class anxieties and fears he will infect his ailing mother, during the Covid pandemic. He needs to make money to keep his mom’s medications in check and pass the Bar exam and land at a top-notch law firm. He needs to live up to the kindness of his mentor Richard, who took him under his wing, after seeing him alone and hitting tennis balls against a wall. Richard teaches Conor a mantra: steady strokes, no big shots. And that holds a key to Conor’s development in The Winner.  He’s methodical and steady with his shots, not prone to long shots or overreaches.  A good-looking Conor has an early fling with a townie waitress named Georgia (she labels him a winner), and then moves his way up the social bedroom scale into the kinky arms of Catherine Havemeyer, garnering $300 a session for very private “lessons.” With a nod to The Graduate, Conor then falls for Catherine’s daughter Emily, an outspoken hipster writer from Brooklyn, who’s a bit estranged from her wealthy mother.  The dark triangle (Conor, Catherine, and Emily) at the novel’s core has been set in motion. Initially, I thought I was entering into a modern Cape Cod reboot of the classic Mrs. Robinson story with Anne Bancroft and Dustin Hoffman, but I was sorely off-track with that early assessment.    

Without giving too much away, Conor juggles the two women through much of the novel, carefully trying to make sure neither woman realizes he’s sleeping with the other. Conor devises new and more elaborate ways to conceal his double life. Sex with Catherine is mind-blowing and life-changing with the wealthy older woman pulling his strings in the affair. However, the relationship with Emily seems filled with future sustainable possibility, even if the sex isn’t going to register on the steamy scale at the moment. Our main character faces an intense moral dilemma between mother and daughter. As the relationships continue, Conor diligently works his way into an interview with John’s firm, all the while studying for the Bar exam. As we get closer to the story’s turning point, Wayne throws a dark twist which changes the entire tone and direction of the story.  And that’s where Macbeth comes in and Teddy’s careful juggling comes undone. No plot spoilers here. All I can say is that I was surprised and entertained by the dark turn in Conor’s tale and wanted to see how his story turned out, especially when the gated life of Cutters Neck is turned upside down. 

Teddy Wayne is noted for his social satires and searing portraits of white male protagonists raging against perceived systems of societal oppression, like Paul in The Great Man Theory or David in Loner.  But, with Conor O’Toole, Teddy Wayne gives us a likeable, good-looking “dinker” and throws him into a dark, twisted, defensive current. The Winner draws on our fascination with true crime stories and anti-heroes, and it plays brilliantly with the American story of “whatever it takes to get ahead.” The Winner plays on the shallowness and hollowness of the American rags to riches tale, by throwing readers into a moral quagmire by the end of the novel.  Is it ok to do whatever it takes to win?   Do we give a pass to the likeable and good-looking and overlook massive moral failures and a lack of empathy or responsibility?  Conor O’Toole is a fascinating character creation, a handsome, working-class guy and future lawyer with a sick mother and a deceased father who committed suicide early in his life. Conor pulls us into his circle, even as he weaves a web of lies, violence, and manipulation throughout this brief summer tennis stint. He defensively volleys his way through the book, trying to use his legal know-how to serve his own dark, selfish interests. Yet, we can’t help but keep reading, hoping to know how he disentangles himself from his own created trap.  Teddy Wayne has created a real dark gem here. The Cape story setting seems primed for a movie adaptation, and the plotline has blood on its hands, which isn’t easily washed off or forgotten.  The Winner serves, dinks, and backhands up a scathing satire, where entitlement and privilege get caught in its own playful, libidinous, and morally ambiguous net. 


The Winner
by Teddy Wayne
Harper; 305 p.

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