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.

Tony and the gang throw Paulie a Bada Bing bash after his release from jail, but it doesn't take long for old tensions to resurface. Carmela's cousin Brian throws out a hypothetical investment scenario that Tony and Ralph attempt to turn into reality with the help of Assemblyman Zellman and a black community leader.

At therapy, Tony likens himself to the 'sad clown,' but Melfi doesn't buy into his melancholy portrait. Meanwhile, Carmela drags A.J. with her to Furio's house to offer decorating tips and companionship; Paulie puts the finishing touches on some free artwork; and Christopher finds himself at a crossroads.

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.

Tony sizes up a contractor's gift, then reunites with his paroled cousin, Tony Blundetto. Paulie and Christopher relive some not-so-special memories. Carmela launches a film club. Adriana grapples with her guilt. A familiar figure 'crosses over.'

Tony's power-sharing plan doesn't fly with Johnny Sack, who makes his point through a bookie named Lorraine Calluzzo. Out on parole, Feech La Manna crosses Paulie in his attempt to break into the landscaping business. Tony gets a roommate. Junior looks into the past while testing the patience of those closest to him.

While Christopher is away, Tony gives Adriana a ride home that proves disastrous. Meanwhile, the Soprano crew plays a game of 'telephone' with the story that turns it into something far more sinister when an enraged Christopher gets wind of it.

A rumor involving his cousin puts Tony's relationship with Johnny Sack back on thin ice. Meadow helps get her boyfriend Finn a job. A.J. ponders a 'maximum-security summer' at Casa Carmela. Melfi links Tony's current guilt to a past job. Carmela learns that good legal help is hard to find.

With the feds pulling a new trump card, Adriana ponders her options. Tony B. unloads some heavy baggage on Tony, and vice-versa. Johnny Sack makes Tony an offer he can refuse, and Tony offers Carmela a deal to make her real-estate dreams come true.

Gene Pontecorvo makes a final break from the mob life, while Junior's paranoid delusions could be the end of Tony.