For more than a half decade now, the two have been working out together, McGrady sharing his deep knowledge of the game with Brown.

Every time the Celtics have entered the playoffs with Jaylen Brown, they've made it past the first round. In fact, the only time the Celtics have been eliminated in the Eastern Conference Semifinals with Brown was in 2019, his third year in the NBA.

Boston Celtics guard Jaylen Brown, left, looks to pass the ball as Orlando Magic forward Paolo Banchero (5) defends during the first half in game 3 of a first-round NBA playoff basketball series,, Friday, April 25, 2025, in Orlando, Fla. (AP Photo/John Raoux) AP