The setting of Teddy Wayne’s sixth novel, “The Winner,” is a bucolic community of mansions on the southern shore of Massachusetts. The town’s name, Cutters Neck, sounds like a warning. And then there’s the ominous question a 50-something divorcee flirtily asks Conor, the young law student who in town for the summer: “You’re not a con man impersonating a tennis pro for some nefarious purpose?” The foreshadowing hardly has any shadows at all.

Conor isn’t a con man, exactly. But the central theme of Wayne’s well-paced, smart, class-obsessed thriller is how easily money can transform and hijack us, turning well-intentioned people into schemers. In tennis parlance, Conor is a “pusher”: He has little finesse or style on the court, but he’s stubbornly persistent, waiting out others’ mistakes. This mind-set allowed him to rise from declassee Yonkers, N.Y., to law school, and from there to a cushy summer job during the pandemic. His attitude also makes him skeptical of the wealthy, though his outrage comes with a caveat. He may live among a “set of passive-income loafers,” but they are partying “on land seized so long ago that they never even considered it stolen.”

Wayne gently guides Conor (and us) away from this benign perspective toward an awareness of something crueler: Old money is nefarious and abusive right now, at this moment, and you’ll have to be that way too if you want to keep up.

The flirty woman, Catherine, hires Conor for tennis lessons that soon become sexual liaisons. His initial doubts are alleviated by the size of her checks, which Conor can put toward his ailing mom’s medical bills. He’d be fully at peace with being the subject of Catherine’s erotic noblesse oblige if he weren’t falling for Emily, a young aspiring novelist he meets. Their love deepens — and then he discovers that Emily is Catherine’s daughter.

Conor’s calculated decision-making around sex and money and ambition suddenly crashes into the realm of Greek tragedy. “He’d have to be willing to hurt her,” he thinks, pondering a breakup. It would be a spoiler to name which woman he’s thinking about. But there’s a fine line between emotional hurt and physical harm.

In structure and plot, “The Winner” has two obvious antecedents: Charles Webb’s 1963 novel “The Graduate” (and the Dustin Hoffman film that followed), in which a college-age man has a sexual relationship with a wealthy older woman while falling for her daughter, and Patricia Highsmith’s Ripley novels, starring a serial killer who murders to preserve the lifestyle to which he’s become accustomed. Working on the first Ripley book, Highsmith wrote in her diary that she was “showing the unequivocal triumph of evil over good, and rejoicing in it. I shall make my readers rejoice in it, too.”

Wayne has taken notes: The tone of “The Winner” has a creepy Highsmithian placidity, coolly measured while depicting bad things being done and cannily covering up the evidence. Conor imagined that his status as a pusher gave him moral superiority over his betters. But pushing in itself is no virtue — we can push toward immoral goals, too.

Though “The Winner” is billed as Wayne’s first thriller, he’s been working up to a book like this. In recent years, he’s developed into America’s preeminent novelist of male entitlement, specializing in guys who think they’re doing the right thing while being blinkered to the bigger picture. In 2020’s “Apartment,” an aspiring writer is consumed with jealousy of a classmate. In 2022’s “The Great Man Theory,” a down-on-his-luck professor directs his fury toward a big-name right-wing TV personality. All figure they’re better and smarter than ends-justify-the-means guys, until the ends become tragically seductive.

“The Winner” is among Wayne’s best treatments of this subject, a savvy take on sex, money and power. (Film rights have been bought, and Wayne is working on the screenplay.) The novel is psychologically alert to how relationships can be manipulated, especially around status-climbing. In that regard, the novel has another, more subtle inspiration: Daphne du Maurier’s 1938 novel “Rebecca,” a classic of whirlwind romance, wealth, secrets and murder. Wayne’s gothic touches keep the second half of the novel from being bogged down by its police procedural plot. He’s researched the whys and wherefores of investigative work, but he stays focused on Conor’s efforts to gaslight everyone around him, including himself.

Throughout, Wayne contemplates the question of how much ambition is too much ambition. His characters rise and fall based on their choices. But Wayne, for his part, gets to have it both ways. He can write a thoughtful novel about moral ambiguity and corruption that’s also a movie-ready page turner, with enough room for a sequel.