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.

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)

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)

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)

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.

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.

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)

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)

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)

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)

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)

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)

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)

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)

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)

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 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)

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)

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)