Tony invests in a land deal despite Carmela's concerns about money. Junior faces his own financial woes as his trial approaches. Adriana brings her new friend to the Soprano Sunday dinner, but Adriana has no idea who Danielle is working for. Tony bonds with Christopher by giving him the opportunity to avenge the murder of his father.

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.

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.'

Friends and family gather at the Sopranos' for a not-so-surprise 75th birthday party for Carmela's father, Hugh. Meanwhile, Johnny Sack shows off his new wheels, Phil Leotardo pulls into Pussy's old place for some auto repairs, and Tony B. considers accepting a familiar job on the side.

In the Season Five finale, Tony's crew circles the wagons as Johnny Sack turns up the heat. Carmela counts her blessings. Christopher is freaked out by an unexpected visitor. Benny's connection to the plumber's union comes in handy. A.J. demonstrates his business acumen. Tony ponders whether to execute a 'sacrifice bunt.'

Christopher's Cleaver premieres, showing Tony how he feels about him. Johnny Sack faces a health crisis. Phil Leotardo resents his family, and himself, for being weak and downtrodden. Silvio gets caught up in New York's power vacuum.

The relationship between Christopher and Paulie's falters, while A.J. grows depressed over his break-up with Blanca.

The Soprano and Lupertazzi crime families quarrel over asbestos removal. Tony deals with a problematic associate. Paulie suffers a devastating personal loss. A.J. questions his friendship with Jasons Parisi and Gervasi.