In the summer of 1967, race riots, caused by the wrongful and brutal arrest of a black taxi driver, set Newark, New Jersey ablaze. These dramatic events cast a chill between mafia boss Dickie Moltisanti (Alessandro Nivola) and his African-American henchman, Harold McBrayer (Leslie Odom Jr.). To the point where the latter leaves the Italian clan to form his own criminal gang.
Dickie becomes a mentor to Anthony Soprano (Michael Gandolfini), the teenage son of a member of his Mafia family. Impressed by this elegant and powerful man whom he considers his uncle, the boy tries to imitate him by indulging in petty trafficking at his high school. However, his actions cause great disappointment to the principal of the school, who was initially impressed by Anthony's exceptional intelligence and sensitivity.