Top 10 Biggest Betrayals on the Sopranos

Tony had high hopes for Jackie Jr. He was keeping away from the family business, doing well in school, and happily dating Meadow. However, the influence of Ralph Cifaretto and the allure of organized crime was just too much. It wasn’t long before Jackie was harboring dangerous ambitions. He ends up turning against the family and robbing a poker game hosted by Eugene Pontecorvo. In the messy process, he shoots Furio in the leg and kills the dealer, Sunshine. It’s a horrible idea that costs Jackie his life. Tony refuses to intervene, and Ralph has Jackie whacked by Vito Spatafore.

Poor Johnny Sack just couldn’t catch a break. If it wasn’t wars with Tony and Little Carmine, it was a betrayal by Jimmy Petrille. Petrille served as Johnny’s consigliere, but he was also working with the FBI. This is a common theme throughout “The Sopranos,” as several characters either turn to the FBI or are revealed to be working for them the entire time. Jimmy Petrille is one of the latter. Petrille feeds the feds enough information to arrest Johnny, and he’s put into prison for the remainder of the series. It’s unclear what happened to Petrille, but it’s likely that he entered Witness Protection and lived out his remaining life as the next Henry Hill.

Junior Soprano serves as the primary antagonist of the first season, and what an antagonist he turns out to be. Through him, viewers are given a fantastic introduction to the hostile atmosphere of “The Sopranos” as Junior tries killing his own nephew. Tony and Junior had been at odds throughout the season, as both had different ideas about how to run the business. However, the last straw came when Junior learned that Tony had been running things behind his back. This prompted Junior to betray his nephew, sending hit men to have him whacked. However, the hit failed and Tony retaliated by killing Mikey and Chucky, which in turn crippled Junior’s power within the family.

Of all the sad sacks on “The Sopranos,” Artie might just be the saddest of them all. Despite desperately wanting to come across as a tough guy, Artie is constantly under Tony’s control. Of course, he gets some nice things out of it, including his fancy Italian restaurant Nuovo Vesuvio. But he only got that because his first restaurant blew up. And it was all Tony’s fault. Junior wanted to kill Little Pussy inside Artie’s restaurant, but Tony believed this would ruin his friend’s professional reputation. Instead, he has Silvio bomb the restaurant so that Artie will remain innocent and claim a hefty insurance payout. Of course, Artie nearly kills him when he finds out the truth…

Before the series begins, Salvatore Bonpensiero is caught trafficking drugs and begins working with the FBI. In order to alleviate his potential 30-year prison term, Sal feeds the FBI information about Tony Soprano and the DiMeo crime family. Sal works closely with handler Skip Lipari, and while reluctant at first, he eventually develops an interest in crime enforcement. Unfortunately, his tenure at the FBI crumbles when Tony discovers the truth. He, Paulie, and Silvio then whack Sal, and his body is dumped into the depths of the Atlantic.

Loyalty is a very tricky concept when it comes to Tony Blundetto. Tony B tries going straight, but eventually returns to the hold. It’s not long however before Blundetto is going behind Tony Soprano’s back, siding with Little Carmine, and killing Joey Peeps. An associate of Blundetto is killed in retaliation, prompting Blundetto to kill Billy Leotardo. To prevent all-out war with the Lupertazzi crime family, Tony personally disposes of his own cousin. It was a tragic and completely preventable death, and it’s made all the worse coming from a close family member.

Despite being one of Tony’s closest associates, Paulie Gualtieri is also one of the most fickle. Paulie becomes increasingly displeased with life inside the DiMeo family and begins harboring thoughts of flipping to the Lupertazzis. He goes straight to Johnny Sack and offers his loyalties. To help sweeten the deal, he even tells Johnny about a joke that Ralph Cifaretto made about Johnny’s wife, nearly getting Ralphie killed. Basically, Paulie almost started a war between the DiMeos and the Lupertazzis. However, Johnny was never serious about taking on Paulie, and he goes back to the DiMeos with his tail between his legs and is nearly killed by Tony for his betrayal.

Of all the monsters on “The Sopranos,” Livia Soprano is the worst. One of the most deplorable characters in all of television, Livia doesn’t have a shred of love for her children, and she even tries to have one of them killed. Tony puts Livia in a nursing home (sorry, a retirement community!), and Livia is so incensed that she tries manipulating Junior into killing him. When that fails, she tells Artie Bucco about Tony burning down his restaurant, in the desperate hope that Artie will kill Tony for her. All of Tony’s near-death experiences in the first season come back to Livia, who certainly isn’t winning any Mother of the Year awards.

The most tragic storyline in the show arguably belongs to Christopher Moltisanti. He tries his best and desperately wants to be respected by Tony, but his poor results constantly undermine his efforts. In the end, the repeated mess-ups prove too much for Tony, and he strangles Christopher to death following a car accident. While Tony’s decision was spontaneous, it was really a long time coming. Tony and Christopher had been at odds for years, and it ended in the ultimate betrayal. Family or not, unending loyalty or not, Tony decided that Christopher had to go. And it was devastating.

The biggest betrayal in the show undoubtedly belongs to Christopher. His fiancée Adriana La Cerva loves Christopher to death, and puts up with his constant abuse. She’s eventually roped in by the FBI but gives them little to work with out of loyalty to her boyfriend. However, the stress eventually proves too great and she reveals the truth to Christopher. While he seems to genuinely consider running away with her, he ends up choosing The Family over his family and has Adriana killed. While it buys him points with Tony, the choice ultimately ruins his life and he falls back into self-hatred, sloppy work, and drug abuse. This, in turn, results in his own death at Tony’s hands.