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.

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.

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.

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

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.

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.”

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.

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.

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.

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.

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.

Vinnie, now a bodyguard for the Profitts, gets his first trial by fire when Mel Profitt, the brilliant but paranoid overlord of an international crime empire, disrupts the wedding of an associate, who retaliates by kidnapping Susan.

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.

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 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.

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 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.

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.

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.

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.

Roger Lococco in effect signs his own death warrant by testifying to a Senate committee about a cabal within the U.S. intelligence community, but to back him up he needs Vinnie to testify as an O.C.B. operative — testimony that would end Vinnie’s career as an undercover agent.

After resigning, Vinnie returns to his old neighborhood to try and get some peace after his life undercover, but is distressed to find white supremists are stirring up trouble. Daryl Elias is promoted to OCB director and orders Frank to either bring Vinnie back to work, or in for debriefing. After a synagogue is trashed, Pete speaks out against the white supremists and is then murdered in a hit and run accident, making Vinnie rejoin the OCB to find his killer.

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. (source: http://www.plasticcow.com/wiseguy)

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. (source: http://www.plasticcow.com/wiseguy)

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. (source: http://www.plasticcow.com/wiseguy)

Vinnie is questioned about his connection to Don Aiuppo, thus learning his mother is dating the retired mobster. Checking into it, he finds Rudy and Carlotta were in love as teenagers, then is stunned when Rudy proposes and she accepts. Mark digs up information showing that Rudy is in the country illegally and sets him up to be deported, not knowing it means that Carlotta will leave, too. At the last minute, Rudy changes places with his brother, Tito, who wants to return to Italy. (source: http://www.plasticcow.com/wiseguy)

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.

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. (source; http://www.plasticcow.com/wiseguy)

Raglin follows Pinzolo's crooked trail into Chinatown, where a garment-worker's strike has snarled an important order for the Sternbergs. Meanwhile, Eli's niece Carole sews up her alliance with Pinzolo. Raglin tries to get Maxine Tzu to realize the strike isn't helping, and they end up in a tryst. (source: http://www.plasticcow.com/wiseguy)

Raglin uncovers evidence that Carole is working with Pinzolo to bankrupt Eli. David confronts Pinzolo and forces him to take him to the bank to give him the money he cheated Eli out of, culminating with David getting killed as a suspected robber. David's death sends Raglin into a tailspin, digging up memories of a past case where another innocent bystander was killed. (source: http://www.plasticcow.com/wiseguy)

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)

Frank shows up at Vinnie's house in the middle of the night and states than his wife is dying and he can't afford the liver transplant she needs to save her life. Vinnie leaves a box containing a million dollars on the front seat of Frank's car. Frank confronts Vinnie about the money and Vinnie confesses it's money Roger gave him as a ""parachute"" in case he ever needed to bail out of undercover work. After arguing with Vinnie about the ethics of using the money, Frank finally decides he'd rather save Jenny's life, so he pays for the operation. Frank and Vinnie turn themselves into Paul for using the money, but Paul dismisses it when he can't find any record of Roger or the money in his files. After Jenny recovers, she tells Frank that their stale marriage is what almost caused her to die, so she insists he move out before she gets home from the hospital. (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)

Frank exchanges Pinzolo's jet with the DEA for a small record company, then allows Vinnie to run it. Bobby Travis talks Vinnie into hiring him by promising Vinnie he'll teach him all he needs to know about the business. Getting caught up in the glamour, Vinnie decides he's going to revive Diana's career by having her cut a record. (source: http://www.plasticcow.com/wiseguy)

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)

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)

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 wants to pull Vinnie off the case when he finds out that D.A. Peter Alatorre plans to expose Vinnie as the head of the Commission in a news conference. Albert is distraught when his son is expelled from school because of his recent press coverage. Rudy calls Alatorre to his hospital room to show that he is back in the country, taking the heat off Vinnie. (source: http://www.plasticcow.com/wiseguy)

Rudy discovers Joey's plan to kill him, Albert and Vinnie, so sets his own plan into operation by convincing Albert he must kill Grosset. Albert and Joey have a showdown that ends with Joey dead and Albert in jail for his murder. Wanting her due, Gina sets up a meet with the Commission to offer them Albert's heroin deal. When Frank easily affects the arrest of the Commission, Vinnie begins to suspect that Rudy set everything up for them. (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)

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)

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)

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)

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)

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)

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)

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)

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 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 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)

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)

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)

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.

While Frank is in Washington to talk to Paul about returning to work, Dan calls to say Vinnie missed his last check-in. Frank goes to Vinnie's house and finds evidence that he was kidnapped. Despite Paul's objections, Frank begins his own investigation, finding out from Carlotta that Vinnie was looking into the death of a priest in El Salvador. Frank follows the trail to Miami and Michael Santana, a disbarred Federal prosecutor, and the last person Vinnie contacted. Santana refuses to help Frank, saying he doesn't know anything about Vinnie's disappearance. Digging deeper, Frank stumbles upon a CIA investigation and is ordered to back off. (source: http://www.plasticcow.com/wiseguy)