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.

With Mel and Susan Profitt undone, McPike begins dismantling their empire, but Vinnie demands to stay on the case to get to the bottom of Roger Lococco’s ties to a rogue CIA operation to stage a Caribbean coup d’etat.

Vinnie and Sonny's right hand man, Tony Grecco, has a run-in with the cops causing Vinnie to be arrested. The Steelgraves find that guns are being exported illegally using their pier and decide to take possession of the guns and sell them back to the owner.

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.

An outraged Sonny Steelgrave accuses Vinnie of betraying him to his arch-rival, then realizes the devastating truth — that his paisan is an undercover Federal agent.

Unbeknownst to Vinnie, his car was used in the robbery where an off-duty cop was killed, leading to his arrest and brutalization at the hands of the NYPD. Frank bails him out, then reluctantly lets Vinnie continue his pursuit of Knox Pooley. Vinnie tells Ritchie he's a cop and asks him to help him gather evidence against the Pilgrims. Vinnie goes to a Pilgrim rally and stumbles across the truck that was used to kill Pete, then agrees to a meet with Stan in the hopes of tying Pooley to it, leading to Stan and Ritchie's arrests.

Mel’s desire to buy a baseball franchise is two-fold: he wants to play on it, and he wants to take it away from an old business associate who cheated him in a Mexican drug deal. When Mel’s former girlfriend shows up, begging for readmission to the Inner circle, he humiliates her, using her as a sexual pawn in a power game with a rival, but for Vinnie, forced to watch it happen, the worst is yet to come.

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.

When some of his munitions contacts begin drying up, Mel decides to blackmail a French Deputy Minister of Defense into supplying him with the weapons he needs.

A psychopathic murderer posing as Sonny's nephew double-crosses Sonny and holds Vinnie's girlfriend Gina hostage.

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.

In an attempt to take over Sonny Steelgrave’s business, mob head Paul Patrice frames Sonny for several murder attempts he makes on the life of the special prosecutor investigating Sonny.

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.

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.

While keeping vigil over Rudy, Vinnie learns that Grosset's father-in-law was also hit, setting up a power struggle within the mob. Albert courts Vinnie's alliance by letting him in on his plan to smuggle millions of dollars worth of heroin into the country. Vinnie goes to the Commission and demands Rudy's seat at the table. (source: http://www.plasticcow.com/wiseguy)

Eli impatiently awaits news from Sri Lanka, where a terrorist's bomb exploded at David's hotel. Vinnie is hit by a taxi, and Frank talks John Henry Raglin into taking over the case when he learns that Vinnie can't return to work for awhile. Eli speaks out against Pinzolo at a fund raising dinner. Pinzolo visits Vinnie in the hospital and Vinnie suggests his partner can take over for him, opening the door for Raglin.

Knox Pooley realizes Calvin is insane and kicks him out, causing Calvin to go off the deep end and take a famous black leader hostage. Richie becomes disenchanted when he realizes Pooley was only in it for the money. Paul Beckstead takes over as director of OCB when Daryl cracks under the pressure and is dismissed for making obscene phone calls.

Vinnie tells Mel Profitt he is leaving to go home to New Jersey, but Mel offers him the biggest cocaine distribution network in the country — a plum that Vinnie feels is too juicy for any undercover cop to turn down.

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.

Vinnie hesitantly goes back to work for the OCB under the promise they will help find Pete's killer, but Daryl is more interested in getting his star agent to work on a ""real"" assignment. Ritchie digs himself in deeper with the Pilgrims of Promise when he uses Vinnie's car to help rob an armored car. Depressed over Pete's death, Vinnie turns to Angie for consolation, but they both agree they don't want to risk their special friendship by becoming lovers. Vinnie talks Daryl into giving him weapons to sell to the Pilgrims, then he throws the bust when he sees they have Ritchie with them.

Feeling lonely, Vinnie joins his old buddy Mike Caccatori at the bachelor party for their high-school friend Jimmy ""The Legend"" Vitale, but the trio's friendship is put to the test when Jimmy reveals that he's broke and owes money to a loan shark. It ends up being a dream. (source: http://www.plasticcow.com/wiseguy)

Steelgrave's former accountant, Sid Royce, is suffering in the Witness Protection life Frank assigned him. When his wife leaves, he snaps and decides to get revenge against Frank for destroying his life. Jenny agrees to have dinner with Frank, then invites him back home. Their romantic evening is destroyed when Sid pulls a gun on them. Jenny talks Sid into letting Frank go by convincing him she's his missing wife. Frank kills Sid in front of Jenny, ending whatever chance they might have had at reconciling. (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)

During a budget meeting, Frank gets a call from Jenny that his father is causing trouble at the rest home he's at. Frank takes Mike home while he looks for a new home for him. Mike tells Frank he's not going to leave until Frank reconciles with Jenny. Vinnie takes Mike to a bar for lunch and the old man gets them into a brawl. Jenny reluctantly agrees to have dinner with Frank and Mike. Mike realizes Frank and Jenny aren't going to get back together, so he allows Frank to find him a new rest home. (source: http://www.plasticcow.com/wiseguy)

Volchek becomes depressed over losing the hospital. Roger and Frank try to save Lynchboro by getting Volchek to realize he really is in control. Vinnie goes to Kousakis when he realizes the waste they're dumping is causing a hepatitis outbreak in a nearby school, then attacks Kousakis when he tells Vinnie to mind his own business. Vinnie tries to alert an official to the toxic waste, but it turns out the guy is corrupt and tells Kousakis to kill Vinnie. Feeling trapped, Vinnie kills the two gunmen sent to kill him, then flees into the night. Roger leaves, telling Frank to tell Vinnie they're now even. (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)

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)

Vinnie and Frank try to cheer up Dan, who's depressed about becoming a grandfather. When Lauren finds a phony check in her husband's pocket, she asks Dan to investigate, and he uncovers a scam a local builder is using to bilk his insurance company. The builder is shut down, throwing Stephen out of a job and making him decide to leave town. (source: http://www.plasticcow.com/wiseguy)

Vinnie attends his 15-year high school reunion and bumps into two old friends, one a mob lawyer and one a detective. Vinnie is torn between telling Denise he's a cop and protecting his cover. Frank tells Vinnie that Denise has bugged his house, making Vinnie furious and determined to teach Denise a lesson. Denise and Mooch get married. (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)

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 takes a job hauling hospital waste as he continues to hide out in Seattle. Frank finds out Volchek is going to bribe a state official to get the license for his hospital and plans to arrest them after dinner. Roger uncovers Volchek's cryogenic vault. Lacey talks to Roger about how important Volchek is to the town, causing him to throw the arrest. (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)

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)

Vinnie is the fall guy in the alleged plot to disrupt the Japanese economy, prompting the Attorney General to launch a classified Senate investigation that could cost Vinnie his badge. Fearing her career is ruined, Kate attempts suicide. After hearing all the evidence, the Attorney General relieves Vinnie of his duties, stating there's enough to prosecute him for treason. Prescott Wilson arrives and places all the blame on Masters. Masters goes off the deep end and kills Strichen. Vinnie is cleared of all charges. (source: http://www.plasticcow.com/wiseguy)

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)

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)

Frank has an out-of-body experience, then briefly awakens when he hears Vinnie calling him. Kousakis kills Harriet, then hides out at the church while waiting to kill Boden. Vinnie decides to try repairing the church bells in the hopes that they will awaken Frank from his coma. Vinnie discovers Kousakis in the bell tower, but Kousakis jumps to his death before Vinnie can summon the police. Vinnie repairs the bells and rings them, waking Frank.

Depressed, Vinnie contemplates suicide, then hears church bells. He goes to confession and breaks down, begging Father Pat to help him. Frank goes to Seattle to look for Vinnie. Vinnie tells Father Pat about the toxic dumping, and the priest arranges a press conference. Frank finally finds Vinnie at the church. Kousakis overhears the plan to expose him on the news and shoots at them, wounding Frank and Father Pat. Vinnie and Dan chase Kousakis. Dan finds out Frank is in critical condition and goes to the hospital. After trying to revive Frank, the doctors give up when he flat lines. (source: http://www.plasticcow.com/wiseguy)

Concerned that Vinnie is addicted to the pain pills he's been taking for his leg, Frank calls in Paul Beckstead, who orders Vinnie to undergo a routine physical exam. At the hospital, Daryl Elias is undergoing therapy and, holding Vinnie responsible for his downfall, he accesses Vinnie's file and orders that he be held for psychiatric evaluation. When Vinnie resists, he is sedated and locked up against his will. While in his drug-induced twilight zone, Vinnie's worst nightmare comes to life in the form of Sonny Steelgrave, who blames Vinnie for his death. (source: http://www.plasticcow.com/wiseguy)