Despite Paul Beckstead's misgivings, Vinnie uses Diana's record to start a bidding war in the hopes of selling Dead Dog to a bigger label. When Vinnie signs elusive James Eliot, Newquay offers to buy Dead Dog without Vinnie, Bobby or Diana. Diana balks at Newquay's offer, revealing they used to be lovers. Contrary to Frank's wishes, Vinnie sells Dead Dog to Isaac. Frank warns Vinnie that Newquay has been digging into Vinnie's past. (source: http://www.plasticcow.com/wiseguy)

Vinnie bails artist Monroe Blue out of jail, then tells him to help Diana work on some songs. Vinnie begins to wonder about Isaac's honesty when he gets a $57,000 bill for bogus record returns. Winston crashes Diana's party to show off Eddie Tempest. Diana succumbs to Winston's charms, then tells Vinnie she has to get out of the country to get away from him. When Vinnie gives Diana money to leave, Winston demands to know where she is, getting furious when Vinnie refuses to tell him. (source http://www.plasticcow.com/wiseguy)

Sensing Eddie's unhappiness with Newquay, Vinnie tries to lure him away by promising him he can work with Monroe. Winston finds out and has Medley thrown off a roof as a warning to Vinnie. Bobby travels to Japan and finds evidence that Twine may be cheating him and Vinnie. Isaac loses Shakala to Newquay in a crooked poker game. Frank talks Isaac into helping him gather evidence against Newquay. (source: http://www.plasticcow.com/wiseguy)

Amber talks Winston into letting her and Isaac run Shakala at Radiance. Feeling like he's at a dead end, Vinnie urges Bobby to make his own way inside Radiance while he starts turning up the heat under Winston. Isaac agrees to dig up information for Frank. Vinnie urges Claudia to take a more active part in Radiance. Eddie is furious when the check he uses to buy his mother a house bounces. Claudia begins an affair with Eddie, and both are killed when they fall through a skylight (source: http://www.plasticcow.com/wiseguy)

Winston serves Vinnie with an order to vacate, which Vinnie counters with the vow that he's going to stay at Radiance for the duration of his contract, causing Winston to dig deeper into Vinnie's past. Winston orders Vinnie and Bobby to work in the mailroom. Bobby uncovers Vinnie's file, which was sent to Winston, and confronts Vinnie about being a cop. Winston is arrested when he agrees to buy the illegal tape of Eddie from Isaac. (source: http://www.plasticcow.com/wiseguy)

Just as Frank's suspected, the case against Winston is thrown out of court as entrapment, pushing the investigation back to square one. Vinnie urges Bobby to start working away at Winston from inside Radiance by contacting all of the acts and showing them how badly Winston has been ripping them off. Isaac suffers a massive heart attack and later dies. Winston goes mad. Bobby gets Dead Dog. Amber gets Shakala back. (source: http://www.plasticcow.com/wiseguy)

Wrapping things up at Shakala, Frank reminds Vinnie that they're scheduled to go fishing in the morning. Vinnie and Amber go to dinner, stay up all night talking. Vinnie is surprised to find they're going fishing with Lifeguard, who is in an emotional struggle over his daughter's plans to marry. Frank, Vinnie and Dan have a long talk about relationships around the campfire. Dan agrees to meet his future son-in-law. Frank tries to reconcile with Jenny. Vinnie decides to go after Amber. (source: http://www.plasticcow.com/wiseguy)

Vinnie warns Amber about her lawyer, but Amber thinks he's just jealous. Vinnie runs into an old high school buddy who urges Vinnie to pursue Amber. Vinnie uncovers proof the lawyer is conning Amber into selling Shakala. Amber and Vinnie fall in love. (source : http://www.plasticcow.com/wiseguy)

Carlotta and Rudy Aiuppo return to the States when they hear about Amber. Carlotta thinks Amber isn't right for Vinnie. Rudy takes Vinnie to the Commission and tells them that Vinnie is under his protection, even though he's not in the business. Frank is overjoyed to learn that Vinnie has been introduced to the Commision. Vinnie tells Amber he's a cop and proposes to her. Rudy is shot, forcing Vinnie to become embroiled in a brewing mob war. (source: http://www.plasticcow.com/wiseguy)

The tension mounts between Cerrico and Grosset over control of the garbage collection business. Grosset forms an uneasy alliance with Chinatown mobster Chin. Carlotta urges Rudy to get better and get Vinnie out of the middle of the impending mob war. The OCB closes down the explosives factory in Chinatown. Gina Grosset kills Chin. After an assassination attempt at the opera, Amber tells Vinnie to move out. (source: http://www.plasticcow.com/wiseguy)

Frank and Dan urge Vinnie to try and reconcile with Amber. At their urging, he goes to her, they make love, then she demands that they see a counselor. Following their therapist's advice, they go away for the weekend, where they both realize they're too involved in their careers to be able to maintain a relationship with each other. (source: http://www.plasticcow.com/wiseguy)

When a local priest finds a box that belonged to Pete, he takes it to Vinnie, who finds a diary of his father's inside. As he reads it, he finds out about a dark episode involving his father and the local mob. The episode uses black and white film and familiar faces to bring John's diary to life. (source: http://www.plasticcow.com/wiseguy)