Michael Kosta interviews journalist Matt Futterman about his new book, *The Cruelest Game*, which explores the psychological toll and unique pressures of professional tennis. They discuss the sport’s maddening scoring system, the intense family sacrifices required, and the mental struggles of players like Naomi Osaka and Coco Gauff. Futterman shares insights on building trust with athletes and highlights the contrasting upbringings of stars like Jannik Sinner and Qinwen Zheng.