The Sopranos

The Sopranos: Law Enforcement Officers, Ranked From Heroic To Most Villainous

Although the Law Enforcement is tasked with taking down the big crime bosses, Tony did manage to get a few of them on his side.

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.

RELATED: The Sopranos Meets Mad Men: 5 Couples That Would Work (& 5 That Wouldn’t)

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

Tony finds Officer Leon Wilmore working as a salesman to pay his bills

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

FBI Agent Harris standing on the sidewalk in The Sopranos

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

Chief Frank Cubitoso suggests bugging the nursing home

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.

RELATED: Made Guy: 10 Frequently Used Terms In The Sopranos & Their Meanings

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

Agent Deborah Ciccerone-Waldrup explains the incident with Christopher

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

Agent Skip Lipari discusses Big Pussy's disappearance with fellow FBI agents

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.

RELATED: The Sopranos: The 10 Best Mob Wives, Ranked By Likability

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.

Officer Danny

Officer Danny stops Paulie to take a bribe

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

Christopher kills 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.

RELATED: The Sopranos: 10 Things The Characters Wanted In Season 1 That Came True By The Finale

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

New Jersey detective Vin Makazian meets with Tony at a secluded spot

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.

Related Articles

Leave a Reply

Your email address will not be published. Required fields are marked *

Back to top button