When 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. Meanwhile, Principal Skinner disappears and the police strongly suspect that Bart and his new friends are responsible.