Content Warning: This article contains discussions/references to violence.
Money was rarely a problem to Tony Soprano and his crew, but they did have several other things to worry about. One of those was the rivalry with the Lupertazzi Crime Family from New York. The feud led to a blood bath that took out some of the major characters. The other thing they had to constantly worry about was law enforcement.
The New Jersey cops were easy for Tony’s DiMeo Crime Family to deal with, but the FBI was a different problem altogether. The bureau was constantly circling around the family, looking for weak members to turn into informants. Thanks to some help from villainous officers, Tony had a good run as boss. However, the formidable officers almost tore his empire apart.
Most Heroic: Officer Leon Wilmore
Leon Wilmore was the only officer who ever stood up to Tony. After seeing Dr. Melfi for the first time together as a couple, Tony and Carmela were pulled over for speeding as they drove back home. Tony attempted to talk his way out of a ticket by mentioning his friendship with a police chief but Officer Wilmore didn’t care. Tony then attempted to give a bribe but Wilmore rejected it.
Felling he had been humiliated in front of his wife, Tony called his politician friend—Assemblyman Ronald Zellman—who arranged for Wilmore to be transferred to the property room. Since his new assignment came with a lower salary, Wilmore was forced to get a side hustle selling household items to pay his bills. Tony later met him working as a salesman and became overwhelmed with guilt.
Agent Dwight Harris
Harris was the key FBI agent hunting down Tony Soprano at the start of the series. In the season 2 premiere, he orchestrated a perfect plan, where his agents pretended to be workers and bugged Tony’s house while everyone was away. Since he was a top agent, he was soon transferred to the FBI’s counter-terrorist division because terrorism had become the agency’s new focus.
The Satriales Pork Store regular later befriended Tony and requested him to give him any leads about terrorist financiers in New Jersey since mobsters normally interacted with all kinds of criminals. Tony did so and Harris returned the favor by telling him about planned attacks on the DiMeo Crime Family by the Lupertazzi Crime Family. By feeding rival families information about each other, Harris made them take each other down instead of the agency having to do the work.
Chief Frank Cubitoso
The head of the FBI’s New Jersey division was constantly looking for new ways to take down the mob. Cubitoso wasn’t easily bribed either. When Tony sent him a deli tray for his birthday, he donated gave it to charity.
Cubitoso is the person who pressured Christopher’s girlfriend Adriana La Cerva to wear a wire. He also came up with the idea of bugging the Green Grove Retirement Community after Tony Soprano and the family capos moved their mothers there so that they could hold private meetings at the facility.
Agent Deborah Ciccerone-Waldrup
Deborah went undercover as a woman named Danielle Ciccolella and befriended Adriana in order to get more information about the New Jersey mob. Posing as a wealthy trophy-wife, she quickly gained Adriana’s trust. She made sure to wear a wire during their meetings in order to record everything Adriana said.
Her position was compromised when Christopher tried to hit on her and lied that she initiated it. As expected, an angry Adriana broke off their friendship. Deborah later revealed her true identity to Adriana and forced her to cooperate with the FBI.
Agent Skip Lipari
FBI agent Skip Lipari became Salvatore “Big Pussy” Bonpensiero’s handler after the DiMeo Crime Family street soldier began providing information to the agency. Since Lipari was Italian-American, Bonpensiero trusted him more.
The two became too close that the lines between work and socializing were blurred. Bonespiero opened up about his frustrations on being passed over for promotions within the family. Lipari had a similar problem too as he had been passed over for a promotion in his FBI field office. Lipari later helped Bonespiero cover up the death of aspiring mobster Matthew “Matt” Bevilaqua.
The New Jersey traffic officer appeared in a single scene where he stopped DiMeo Crime Family Capo Paulie’s car. When he approached, Paulie pulled out a gun and joked about shooting him because he was wearing vest.
The two had a brief friendly conversation during which Officer Danny assured Danny that he would make sure the police looked the other way during Tony Soprano’s executive poker game. Before driving away, Paulie then handed Danny a roll of money, proving that the officer was indeed dirty.
Officer Barry Haydu
Barry Haydu had worked as a police officer in Clifton for 30 years. Since he had serious debts, he decided to become a contract killer to get more money. When Christopher’s father, Dickie Moltisanti, severely injured Jilly Ruffalo, in a prison brawl, Haydu was hired by Ruffalo to kill Dickie.
After Haydu’s retirement, Tony no longer needed his services so he finally let Christopher know about the officer’s involvement in his father’s death. An angry Christopher then broke into Haydu’s house and shot him twice.
Villainous: Detective Vin Makazian
Vin worshipped Tony Soprano. When the New Jersey mobster tasked him with digging up more information about his therapist Dr. Melfi, he was more than glad to do so. He kept tailing her, going as far as to invade her privacy and beating up the male companion that had accompanied her on a car ride. He had the false impression that she was Tony’s mistress and she was cheating on him.
The Newark police detective was also the person who informed Tony that DiMeo soldier, Salvatore “Big Pussy” Bonpensiero, was an FBI informant. Though he was right, he desperately wanted Bonpensiero to get killed so that he wouldn’t have to pay the $30,000 he owed the mobster. He was willing to break the law for Tony if it meant impressing him.