Uncle Junior enjoys a romantic tryst in Boca with his girlfriend Bobbi, not realizing that she's been gabbing to her beauty-parlor friends about his oral talents. Meanwhile, controversy arises when Meadow's soccer coach announces he's leaving the school.

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.

Engaged lovebirds Richie and Janice have an explosive first quarrel. Meanwhile, Irina takes drastic measures to try to convince Tony to continue their affair.

Bobby 'Bacala' Baccilieri Sr. comes out of retirement to deal with a young hothead named Mustang Sally--much to the chagrin of his son and Uncle Junior.

Silvio and Ralph must take care of a planned protest of the Columbus Day parade by a Native American group. At an Italian pride ladies' lunch, Carmela is embarrassed by anti-Mafia remarks. Meanwhile, Ralph deals with new relationship troubles, and Bobby receives some tough news.

Checking out Ralph's promising new filly at the track, Tony displays a flair for horse-racing strategy--and discovers an unexpected affinity for the stable life. Adriana finds her rock club being used as a place of business for Chris and his pals. Meanwhile, a court artist incurs the wrath of Uncle Junior, and Janice feeds Bobby in his hour of need.

After an aggressive team of reporters lowers the boom on Uncle Junior, his lawyers try a new strategy. Ralph has some fun at the expense of Paulie and his mother, but soon winds up with his own family problems. Meanwhile, Tony again finds refuge at the stables.

After a sitdown with Carmine and Johnny Sack, Tony contemplates the future of the HUD partnership. Meanwhile, Paulie blows off steam with an old pal; Janice starts losing patience with the obsessive Bobby; and Melfi ponders the Freudian undercurrents of Tony's latest dreams.

Tony continues to haggle with Johnny Sack and the two Carmines over the Esplanade profits. Carmela makes a decorating date she can't keep; Furio proves a reluctant companion to Tony on a casino junket; Paulie plays an impatient chaperone to some ladies from the nursing home; and Meadow debates the true meaning of a literary classic with her mom.

In the Season Four finale, Tony and Carmela contemplate purchasing a shore house, but a voice from the past threatens the deal. While Uncle Junior breaks out the Hearty Burgundy, Little Paulie and Benny break in a new sound system on the Stugots. With Carmine apparently intent on putting the past behind him, Tony and Johnny Sack weigh their options, carefully.