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 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 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.

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 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)