John McEnroe invites Graham to both his tennis academy in New York City to reflect on his reputations as both a tennis superstar and a short-tempered bad boy in the sport. McEnroe shares stories of his rise to stardom, his love-hate relationship with anger and coping with the 2017 deaths of both parents. Plus, the tennis star turned TV personality talks of his fondest memories as a commentator and what life might be like once the celebrity spotlight fades.Later on, McEnroe shares stories pertaining to his highs and lows of collecting art over the years, including taking significant financial gains buying and selling famous pieces and the regret of selling early in some instances.