Season Two opens with the aftermath of the federal crackdown: Junior's in jail, Melfi refuses to see Tony, Christopher's expanding into new business ventures, Pussy is still missing...and Tony's adjusting to life as the new boss. To complicate matters even more, Tony's free-spirited sister Janice arrives to take care of Livia.
When black protesters start picketing a construction company that used to be under Uncle Junior's control, Tony meets with the owner--as well as the leader of the protestors--to 'fix' the problem. Meanwhile, Janice gets sucked into Livia's web.
Tony busts Meadow for partying at his mother's old house. Meanwhile, Ritchie Aprile is out of the can after ten years and looking for action--much to the chagrin of a local pizza-shop owner.
Tony travels to Italy with Paulie and Christopher to jump-start a car-importing 'business.' While Paulie and Christopher sample some of the Old Country's choicest wares, Tony haggles with the head of a powerful Naples family and recruits a valuable new lieutenant named Furio.
Back in Jersey, Furio soon lives up to his name by unleashing his fury on the delinquent proprietor of a local 'tanning salon.' Dr. Melfi shares her guilt over dumping Tony as a client during a session with her own therapist. Meanwhile, Tony learns from Hesh that his father had emotional secrets of his own.
David Scatino, the father of Meadow's friend Eric and the owner of a local sports store, gets on the bad sides of both Richie and Tony when he loses big in two poker games. Paying his respects at a funeral, Tony is forced to deal with the presence of Livia.
With Anthony Jr.'s confirmation approaching, Tony and Carmela find their son's growing apathy a cause for concern. Meanwhile, Christopher's interest in show biz is reignited when he meets a well-known filmmaker through his cousin's girlfriend.
Although Richie is miffed at Tony for forcing him to build a ramp for the pizza-parlor owner he paralyzed, he decides to make a peace offering. Unhappy with their lowly status as Christopher's lackeys, Sean and Matt decide to pledge their allegiance to Richie--through a violent, unexpected act.
Christopher has an out-of-body experience that spooks Paulie to no end. Carmela urges Tony to have a vasectomy. Visiting her own psychiatrist, Melfi reveals the 'unholy alliance' she's made with Tony...as well as her growing dependence on pills and alcohol.
Richie meets with Tony to complain about his end of the garbage business, then meets with Junior to complain about Tony. Later, Tony orchestrates the 'planned bankruptcy' of David Scatino's sporting-goods store while Scatino's wife introduces Carmela to her handsome widowed brother.
Having dodged a legal bullet, Tony is advised by his lawyer to spend more time at his businesses. Junior looks for diversions to relieve the tedium of house arrest, and eventually finds one in the company of a police widow. Meanwhile, Melfi's problems boil over while eating dinner with her son.
Engaged lovebirds Richie and Janice have an explosive first quarrel. Meanwhile, Irina takes drastic measures to try to convince Tony to continue their affair.
In the Season Two finale, Tony has a series of 'fever dreams' that help to shed light on some of his problems--particularly his troubles over Big Pussy.
