A miserable conman and his partner pose as Santa and his Little Helper to rob department stores on Christmas Eve. But they run into problems when the conman befriends a troubled kid.
Set 13 years after the first film, Willie Soke remains depressed as ever, upset his "happy ending" did not pan out, as he is again addicted to sex and alcohol. As he tries, and fails, to kill himself, he is visited by Thurman "The Kid" Merman, who has just turned 21 and works at a sandwich shop. Unfortunately, Thurman's father has abandoned him and his grandmother has passed on two years before - making Willie the closest thing to family he has left. Thurman delivers to Willie a package containing a large sum of cash, and Willie soon finds out it's from Marcus, his former partner who has been released from jail after the events 13 years earlier. Marcus, expressing sincere remorse for betraying Willie, tells Willie he has an opportunity in Chicago, a deal that can potentially net them millions, though he is unwilling to disclose the name of his contact. Willie reluctantly agrees, while unsuccessfully trying to help Thurman lose his virginity before he leaves for Chicago.