After a miserable day in which Bart had nothing go right for him, he crashes his skateboard into the stairwell of the Legitimate Businessman's Social Club; Bart falls in with a particularly bad crowd: the Springfield Mafia. Soon, he befriends Fat Tony, Louie, Joey and other goodfellas, who take him on as their bartender and errand boy. As Bart adopts more and more gangster-like traits, Marge grows anxious. That is proven true when Bart had cartons of cigarettes hidden in his room. After Skinner sentences Bart to an afternoon of detention, he disappears and the police strongly suspect that Bart and his new friends are responsible. During the sensational trial, Fat Tony turns stool pigeon and rats out Bart as Skinner's killer. Nobody can save Bart but Skinner himself, who emerges from his hiding place to explain that neither Bart nor the Mob did anything to him and that he disappeared after being trapped under a pile of newspapers. Bart snubs the mafia and returns home, safe from a life imprisonment.