Sonny’s impending marriage to a syndicate boss’ daughter begins a supposedly businesslike realignment of “families,” but Vinnie learns that the wedding is a pretext for a bloody gang war.

Sonny’s cruel punishment of a lounge singer who wants out of his contract triggers a cascade of events that leads to Vinnie’s being photographed with McPike — a photo that is to be delivered to Sonny.

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)

After Susan is arrested for Mel’s murder, Vinnie refuses McPike’s order to pull out of the Profitt case, because Susan, who has seemingly lost her grip on reality, has told him she is pregnant with his child.

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)

Vinnie and Dan find evidence of the counterfeiting ring in Utah, but it seems to have come too easily, so Vinnie heads into the mountains to meet a billionaire recluse, Prescott Wilson, who might hold the key to the truth in the case. Frank and Vinnie convince Senator Pickering to delay passage of Senator Getzloff's trade bill while they search for the plane carrying the yen. Masters presents the Attorney General with photos of Vinnie and Kate talking with Wilson, as well as the printing plate with Vinnie's prints on it. Frank is ordered to arrest Vinnie. (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)

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)

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)

In the aftermath of economist Valenti's assassination, new paths open in Vinnie's investigation of the plot to disrupt the Japanese economy. Although Vinnie strongly suspects that Masters is behind the plot, he follows the trail Masters sets out for him. Vinnie and Kate both go to Utah to track down the mysterious Mr. Wilson. (source: http://www.plasticcow.com/wiseguy)

Vinnie calls in Roger Lococco to take over the case, then holes up in a seedy hotel in Seattle. Frank is more interested in looking for Vinnie than in nailing Volchek. Paul orders Frank to continue the case and offers him another agent, which Frank refuses. Roger takes over as sheriff. Dan moves to Seattle to support Frank and look for Vinnie. (source: http://www.plasticcow.com/wiseguy)

In the aftermath of the Steelgrave case, Vinnie tries to vindicate himself of his lingering feelings of betrayal and disloyalty by risking his life to save an old friend from the Brooklyn neighborhood who has a contract out on him.

Hiding out in Vancouver after the fall of the Steelgrave empire, Aldo Baglia sees a photo of Vinnie in the paper and decides to even the score, sending Vinnie into a coma from two serious gunshot wounds. Roger, using his CIA contact, tracks down Aldo.

After rejecting an offer to finance a coup d'etat in the Caribbean, Mel Profitt becomes obsessed with a supposed voodoo death curse, and Vinnie, horrified, can only watch as Mel’s personality begins to disintegrate.

When garment manufacturer Eli Sternberg cannot get a loan to bail out his business, he turns to mobster Ricky Pinzolo for the money. David goes to the OCB for help when he finds out Eli is in debt to the mob. Vinnie meets with David, then reluctantly agrees to take the case, running into opposition from Eli, who doesn't want a hood working for him. Pinzolo demands that Vinnie keep him apprised of everything going on. Vinnie wins Eli's trust when he gets a delayed shipment released from customs.

Vinnie is called to Washington to investigate a counterfeiting operation designed to sabotage the Japanese economy. Frank warns Vinnie to be careful, that there is some kind of power play going on, because Paul was mysteriously sent to Thailand, leaving Mark in charge. Vinnie suspects Masters wants to set him up for throwing the coup of Isle Pavot. Mark is relieved of duty when he loses control after his former mentor is murdered. Vinnie meets Kate Gallagher. (source: http://www.plasticcow.com/wiseguy)

Frank's reporter friend tells him about a corrupt town in Washington, spurring Frank to assign Vinnie to the case. Vinnie sets his cover as a truck driver whose rig just got repossessed. The local sheriff investigates Vinnie and finds out he used to be a cop, so he offers him a job as deputy. Vinnie prevents Bobby from killing Volchek, then fakes Bobby's death to win Volchek's trust. (source: http://www.plasticcow.com/wiseguy)

Vinnie is released from prison where he has been for two years to establish his cover. He meets his boss, Frank McPike and gets to see his coach and mentor, Jerry Greco. Greco is killed and Vinnie demands to be put in to finish the investigation. He uses his ingenuity to get a foothold in the Steelgrave crime family, but it will take a while to finish this job.

After his mother is mugged in Brooklyn, an enraged Vinnie sets out to find the punk who did it, but when he visits his mother in the hospital, it breaks his heart that she still won't forgive him for his life of “crime.”

Vinnie’s assignment to check out a contract killer leads him into a huge global contraband syndicate — an operation that far exceeds the scope of the Steelgrave family — overlorded by brother and sister Mel and Susan Profitt.

After his munitions operation starts falling apart, Mel orders Vinnie to set up a meet with the mob to use his immense cocaine trade to regain financial power.

Raglin pursues a lead that David left him about Pinzolo's murderous past, but they can't find the body. Eli offers Raglin money to kill Pinzolo. Raglin urges Frank to get Carole to testify against Pinzolo, but she has been killed. Revealing that the reason he quit undercover work is because he was tortured into giving up two fellow agents, Raglin vows to bring this case to a successful conclusion. Deciding things are getting too hot for him in the States, Pinzolo plots an escape to Morocco. Raglin confronts Pinzolo at the airport, and when Pinzolo figures out Vinnie is a cop, Raglin kills him. (source: http://www.plasticcow.com/wiseguy)

When the bodies of two missing deputies turn up, it points to a serial killer who has been terrorizing the northwest. Volchek assigns the investigation to Vinnie when Stem loses control. Frank warns Vinnie he has to leave after Dan tells him there's a 40 man task force on the way to Lynchboro. As Volchek tries to eliminate possible suspects, Stem confesses to the murders, then electrocutes himself. Vinnie flashes back to Sonny killing himself, then snaps and takes off, stealing Frank's car.(source: http://www.plasticcow.com/wiseguy)

Vinnie nearly blows his cover when he becomes obsessed with finding out who killed his cousin, causing Frank to threaten him with dismissal. Frank desperately wants Vinnie to concentrate on nailing the Zaratzos, who are trying to arrange a drug smuggling deal with Sonny, because they killed one of Frank's agents.

After several deals go sour, Sonny starts suspecting Vinnie may be a plant. Frank orders Vinnie to drop the case when he finds out the local police have an informer in Sonny's operations. Sid has Frank picked up and tortured, but Vinnie and undercover cop Karen Malloy rescue him. Karen's disappearance points the finger at Sid as the leak.