The film opens with a documentary-style overview of Uncle Drew, a well-remembered basketball legend who was supposed to play in the Rucker Classic. However, due to an unknown conflict, he and his team disappeared. In the present, Dax is the under-appreciated coach of the Harlem Money and their star player, Casper Jones. Dax spends lavishly to keep both his girlfriend, Jess, and Casper happy, despite being a clerk at Foot Locker. During practice Mookie, an old rival of Dax's, arrives and taunts him about the upcoming Rucker Classic tournament. In a dream sequence, we learn that Dax was an orphan who planned on becoming a basketball player, but was humiliated by Mookie after he had a shot blocked by him in their youth. The next day at work Casper demands expensive new shoes from Dax, who effectively bankrupts himself purchasing them. Despite this, Mookie successfully recruits Casper and the rest of Dax's team away from him, leading to a confrontation involving Dax forcibly trying to remove Casper's shoes that is filmed and shown on ESPN. Due to this humiliation, Dax's girlfriend Jess dumps him and kicks him out of her apartment..