Don’t hate the player: Review of The Winner by Teddy Wayne

F. Scott Fitzgerald told us that the very rich are different from you and me. The main character of Teddy Wayne’s sixth novel, who gains admittance to a rarefied realm of the super-wealthy near Cape Cod, is acutely aware of how far he stands apart from those sitting pretty. But instead of keeping his distance, Conor O’Toole plans to integrate himself into this gilded world. An opportunity comes his way early on when he is asked if he would like to come to a party — providing he doesn’t mind mingling with a group of Wasps. “As long as the Wasps don’t sting,” Conor replies. What follows is a gripping high-stakes tale of dangerous liaisons, grand deception, and ruthless ambition.

The Winner begins with an outline of protagonist and place. Conor is 25, shares a cramped apartment with his diabetic mother in Yonkers, and has just graduated from an undistinguished law school. He has come to Cutters Neck, a gated community on a two-mile strip of land protruding from the southern shores of Massachusetts, to put his tennis talent to good use. He has secured a good deal with lawyer John Price: rent-free accommodation in a waterfront cabin over the summer in exchange for giving tennis lessons six days a week to his employer-landlord. Price has allowed Conor to turn a profit by teaching other, paying residents. The income will come in handy: Conor can repay hefty school loans and provide lifesaving medication for his mother. His free time will also be beneficial: He can study for the bar exam and send off job applications.

It isn’t long before Conor is coaching Catherine Havemeyer, a beautiful but arrogant and acerbic divorcee and shipping heiress almost twice his age. He quickly realizes this is a woman used to getting her own way. During lessons, she expects a hands-on approach and proves it by audaciously flirting. After lessons, she insists that Conor come back to her house to drink cocktails and pick up his check. She starts to pay him double his normal rate. Eventually, and inevitably, she propositions him with payment for a service he has to carry out not on the court but in one of her 10 bedrooms. 

“Conor had had no shortage of attractive girls coming on to him,” Wayne informs us. “But none of them was the owner of a $26 million mansion overlooking the ocean that supplemented a Fifth Avenue ‘turret.’” After much deliberating, Conor surrenders to his desires and an illicit, erotic affair develops. It’s a win-win arrangement for both parties: Catherine gets to call the shots and remain in control; Conor enjoys a series of earth-shattering, mind-blowing sexual encounters, the best he has ever experienced, and uses the payment for them to buy insulin for his mother. As Catherine’s off-court escort, Conor fully understands the transactional nature of the romance. But he is more than happy to keep playing her game by her rules. As he puts it: “It was as demeaning as it was titillating.” 

The situation changes when Conor meets a woman nearer his own age. Emily is an aspiring writer who has come up to Cutters Neck from Brooklyn. She has a trust fund that keeps her financially afloat, but she is no spoilt and entitled brat. A past breakdown has rendered her fragile, but she is no pushover. Conor finds her wittier, worldlier, and smarter than he is, and soon he is immersed in a deeper, more meaningful relationship with her — while still clandestinely pursuing his passionate fling with Catherine.

And so Conor tries to tread carefully, “to negotiate between the two women with vigilance and skullduggery.” He is plagued by guilt and self-doubt and evaluates the type of man he has become: “The kind who’d started with a minor impropriety, a brief lapse in judgment, then a bigger one and a bigger one, the ligament stretching like taffy, until one day it snapped like a wishbone.” Then, when Catherine learns he is seeing someone else, she threatens to destroy his future prospects. Suddenly this winner has everything to lose. Can he still come out on top?

There is far more to this novel, including shock disclosures and desperate measures involving subterfuge and violence. However, to reveal more would be to spoil all. Suffice it to say, Wayne’s narrative changes gear in the last third of the book as an increasingly frantic Conor makes the transition from hero to antihero. What started out as a sharp comedy of manners about the carefree lives of the careless rich becomes a fast-paced psychological drama with hidden depths and dark undercurrents. 

The literary thriller is new territory for Wayne. He has revealed that during lockdown he consumed novels that twisted and turned while opening his eyes to different aspects of the world. The Winner was his attempt at a thought-provoking entertainment, a book that was at once incisive and propulsive. For the most part, he pulls it off expertly, keeping his reader hooked throughout all of Conor’s exploits, from his sure-footed moves to his calamitous missteps.  

But some of those exploits strain credulity. Why would Conor invite a group of townies he barely knows into Cutters Neck and give them the gate code to boot? The implausibility of the deed kills the tension stone dead. Other actions, certain sexual shenanigans with Catherine, so obviously signpost trouble ahead that it comes as no surprise when their consequences hit Conor hard. Fortunately, Wayne is more successful elsewhere at hoodwinking us and creating an atmosphere of queasy dread.

If this is a new genre for the Whiting Award-winning author, then it is business as usual when it comes to the book’s setup. Wayne’s previous fiction has taken the form of a male protagonist making his way, or coming undone, in a circumscribed milieu. An 11-year-old heart-throb and preteen pop poppet grapples with the fame game in The Love Song of Jonny Valentine (2013). An awkward and deluded sad-sack freshman at Harvard University tries to shrug off his anonymity and win over the classmate he is obsessed with in Loner (2016). And a self-confessed “curmudgeonly crank” who suffers one hard knock after another searches for relevance and connection in the modern world in The Great Man Theory (2022). 

Conor is perhaps closest to the hero of Wayne’s 2010 debut novel Kapitoil, a Qatari computer programmer who travels to New York City in 1999 to help prevent a millennial meltdown. Both characters are savvy strangers in a strange land, fish out of water that don’t flounder. Just as Karim Issar offers a foreigner’s unique perspective on American culture and Western capitalism, so too is Conor a keen-eyed outsider looking in on the charmed lives of the elite.

Once again, Wayne compels with his examination of power imbalances and class divides. Conor rubs shoulders with privileged youngsters who have “safety nets of money and nepotism” and older types for whom “money was a kind of vaccine,” a means of inoculation from COVID and other indignities. Catherine always keeps Conor in check with her authority and social standing, “her oceans of money compared with his dirty puddles.”

Equally effective is Wayne’s depiction of Conor’s two markedly different relationships, one powered by love, the other fueled by lust. “If being with Emily gave him unwavering safety and closeness,” Wayne writes, “being with Catherine was like skydiving with a parachute that threatened not to open each time, until it did at the very last moment.” For Conor, this sense of jeopardy is replaced by a whole new level of intensity in the book’s fraught last act. For the reader, following a man playing with fire while trying not to get burnt makes for an exhilarating reading experience.

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Malcolm Forbes has written for the Economist, the Wall Street Journal, and the Washington Post. He lives in Edinburgh.