Why does tennis drive so many of its top athletes mad, leading some to quit at the peak of their career? Matthew Futterman explores this question after several years of full-time tennis writing for the Athletic, the sports arm of the New York Times.

This is Futterman’s third book. His first, Running to the Edge, chronicled a group of Olympic runners and their visionary coach. His second, Players, explained how sports became big business.

Futterman is a veteran sportswriter who has covered many Olympic Games and World Cups, as well as the NFL and NBA. But the tennis beat hit different. “I was completely blown away, immediately, by how miserable tennis players were,” he said in an interview on The Tennis Podcast.

Tennis pros might be miserable because of the sport’s gruelling season, which spans 11 months and six continents. Or because the sport lacks a bona fide players’ union, leaving athletes to labour as independent contractors without a safety net.

Or it might be the money. Fabulous wealth awaits the sport’s top athletes, but those outside the top 100 often scrape by. “The hundredth-best basketball player in the NBA is likely making $12 million a year,” Futterman writes. “The hundredth-best tennis player is struggling to break even.” Thus, the reality for most pros is “(w)orkaday matches against no-names in odd locales in front of sparse crowds.”

Those who reach the sport’s pinnacle sometimes experience it as a precipice. “When I win I don’t feel happy, I feel more like a relief,” Naomi Osaka, a four-time Grand Slam champion, says. “And then when I lose I feel very sad. And I don’t think that’s normal.”

The Cruelest Game focuses on the 2020s — a decade of transition in tennis — with occasional forays into earlier decades. Superstars and prominent rivalries get their own chapter, while emerging players share a chapter or get a few pages each.

Futterman is fascinated by “the codes” of tennis. They are the keys that unlock a player’s ability to thrive on tour, a precise and personal balance of excellence and happiness. He believes a player can know the codes but not have the talent to realize them, or have raw talent in spades but find the codes elusive.

Tennis writers come in several varieties. Futterman is the sort who focuses on personalities and narratives rather than statistics and matches. He wants to know what makes a player tick, on and off the court, and excels at unpacking the mental side of the game, rendering vivid portraits of intense and contradictory icons such as Novak Djokovic, Andre Agassi, and Iga Świątek.

Great writing makes the familiar strange; Futterman excels at revealing the weirder norms of tennis, like eight-year-olds shipping off to training academies and 15-year-olds turning pro. A chapter on the parent-as-coach dynamic brilliantly juxtaposes Grand Slam finalists Casper Ruud and Stefanos Tsitsipas, yielding a fascinating study in contrast. “Tennis is about as small and incestuous a sport as there is,” Futterman writes. “Nearly everyone is somehow related — either by marriage or blood or a coaching tree or a representative.”

Futterman manages to secure a jaw-dropping amount of access to top players. If a pro isn’t particularly articulate or introspective, he seeks out their coach or trainer, especially those who have helped champions find or recover the codes.

Futterman isn’t an elegant writer, employing clipped sentences and the occasional awkward wording. Certain passages read like they were written too quickly and edited too lightly. One page appears to contain two versions of the same paragraph.

Content to describe, he doesn’t wade into ongoing debates about how to make professional tennis less cruel. A follow-up book could explore the sport’s political and structural issues.

Jordan Ross is a Winnipeg writer and recreational tennis player who recently became a dad. If his son shows an interest in tennis, he’ll let someone else coach.