10 Most Brutal Betrayals on ‘The Sopranos,’ Ranked

The Sopranos is one of the best television dramas of all time that forever changed the world of television as well as the modern gangster genre. With an array of exceptional performances by an all-star cast including James Gandolfini, Edie Falco, and Michael Imperioli, David Chase‘s award-winning series continues to be one of the most watched (and rewatched) shows today, which captivated audiences with its memorable characters and distinct writing that left fans desperately wanting more.

Like most stories centered around the mafia, betrayal is one thing that can be expected, and when it comes to the backstabbing and double-crossing in The Sopranos, some are simply for the ages. Out of all the moments of disloyalty and deception, including Tony giving Christopher the Cosette treatment and Livia Soprano (Nancy Marchand) manipulating Uncle Junior (Dominic Chianese) to do her bidding against her son, these are the ten most brutal betrayals from The Sopranos, ranked.

10. Matthew and Sean’s Unsanctioned Hit on Christopher

“Full Leather Jacket” – Season 2, Episode 8 (2000)

When Matthew Bevilaqua (Lillo Brancato Jr.) and Sean Gismonte (Chris Tardio) become fed up with being treated like errand boys, they make the very poor decision to whack Christopher (Michael Imperioli), thinking it would get them points from Richie Aprile (David Proval). Not only does the hit go terribly wrong, Richie has the exact opposite reaction to Chip and Dale’s actions and Matthew is soon a man on the run with nowhere to hide.

It’s hard to understand why Matthew and Sean ever thought that killing Tony’s nephew would somehow earn them points. Even if Richie had a different reaction, he could never have protected them from Tony’s wrath. Thankfully, Chrissy survives, but Matthew and Sean’s decision to not only go after the one person who brought them into the fold but also someone who is considered to be a second son to a mob boss ranks as one of the most brutal (and senseless) betrayals in The Sopranos.

9. Dr. Melfi Refusing to Help Tony

“Guy Walks Into a Psychiatrist’s Office…” – Season 2, Episode 1 (2000)

In “Guy Walks into a Psychiatrist’s Office…,” Tony almost passes out while driving and decides to try and talk to now-famed TV Dr. Melfi (Lorraine Bracco) and convince her to take him back on as a patient. Unfortunately, the good doctor is still upset with how the recent events in Tony’s life forced her to essentially uproot her own life and practice. Despite his best efforts, Melfi also shares that while she was “on the lam” because of Tony, one of her patients died by suicide, which she blames on Tony.

In fairness, Melfi does have the right to be upset about her patient, but it’s pretty unfair and unprofessional for her to use that as a reason to refuse Tony treatment. As her psychiatrist (Peter Bogdanovich) points out to her, she was still able to see her patients and communicate with them, so it’s not as though the inconvenience of her situation prevented her from seeing or treating her other patients. While the loss of her patient is understandably upsetting, Melfi turning Tony away is not only negligent on her part, but it’s also kind of hypocritical to refuse treatment for someone who could end up dead because of her.

8. Tony Burning Down Artie’s Restaurant

“Pilot” – Season 1, Episode 1 (1999)

When Tony learns that Uncle Junior plans to whack Gennaro “Little Pussy” Malanga at Artie Bucco’s (John Ventimiglia) restaurant, Vesuvio’s, he thinks the incident will end up hurting his friend’s business and tries to convince his uncle to execute the hit somewhere else. With Junior refusing to change his mind and Tony exhausting other options, he decides to blow up Vesuvio’s, thinking Artie will be able to collect on the insurance and build a new place. Unfortunately, the loss of the restaurant forces Artie and his family to move to a new house and endure the stress of several investigations from the insurance company.

Tony’s decision to blow up Artie’s restaurant in the pilot episode is another baffling but cold betrayal that caused more harm than good. While the hit may have damaged Artie’s business and reputation, who is to say the restaurant couldn’t have been salvageable? Or even boosted its popularity? It’s not a secret that many people are fascinated by organized crime and may have started to flock to Artie’s because of the hit (as morbid as that may seem). Either way, if Tony had just chosen to stay out of the situation, at least, then he wouldn’t have brought more stress to his life, as well as put a strain on his friendship with Artie, and have him go through an intense arson investigation.

7. Tony’s Constant Cheating on Carmela

“Whitecaps” – Season 4, Episode 13 (2002)

Throughout the series, Tony consistently cheats on Carmela (Edie Falco) with other women and, while she is aware of her husband’s infidelities, her only rule has ever been for Tony to keep that part of his life separate from his life at home with her and their children. In one of The Sopranos’ most important episodes, “Whitecaps,” Carmela reaches her limit when Tony’s former goomah, Irinia (Oksana Lada), calls the house while drunk and speaks to AJ (Robert Iler). To make matters worse, Irina tells Carmela that Tony slept with her cousin, who Carmela had met when she was hired to care for Tony’s mother.

When it comes to the mob, goomah have always been somewhat acceptable and considered part of life, but that doesn’t mean it’s still not a devastating betrayal, especially in the instance when Tony cheated on Carmela with someone she personally knew and had spent time with her and their family. Even though Irinia had drunk dialed the Soprano’s home before, her actually speaking to AJ was a huge violation that probably would still have fueled an argument between Carmela and Tony, but between the sudden departure of Furio (Federico Castelluccio) and Tony trying to compensate his love for his wife with a house by the shore, it’s easy to see why this betrayal was the final straw for her.

6. Paulie Walnuts and Johnny Sacramoni

“Calling All Cars” – Season 4, Episode 11 (2002)

When Paulie (Tony Sirico) becomes unhappy with how Tony is treating him, he decides to vent his frustrations to New York’s underboss, Johnny Sacramoni (Vincent Curatola), ultimately breaking a vital rule of this thing; never discuss anything outside the family. As Johnny earns Paulie’s trust with lies about Carmine (“He asks about you”) and pandering to his complaints, Paulie eventually reveals the deal with Ronald Zellman (Peter Riegert), which Tony failed to mention to New York. Paulie’s betrayal cuts even deeper when he tells Johnny about Ralph Cifaretto’s (Joe Pantoliano) insensitive joke about his wife, causing tension between the two families.

When Paulie talks to Johnny Sack in “Calling All Cars,” he lets his personal feelings get the best of him, breaking a major cardinal rule and rightfully earning a place on this list of brutal betrayals. Paulie is one of several characters in The Sopranos who is a top fan favorite, so it’s a bit shattering when he shares vital information with Johnny, which leads to serious conflict between Jersey and New York as well as trust issues for Tony and his crew. Even though fans still have a soft spot for Paulie, there’s no denying that he senselessly betrayed Tony and the guys all because his feelings were hurt.

5. Tony Blundetto Killing Joey Peeps

“Marco Polo” – Season 5, Episode 8 (2004)

At the beginning of Season 5 of The Sopranos, several mobsters are released from prison, including Tony’s cousin, Tony Blundetto (Steve Buscemi), who initially wants to try and lead a normal, law-abiding life. While some tensions arise with the class of 2004 re-adjusting to this thing and taking orders from some of the younger guys, Tony B. is the one who ends up causing the most problems for Tony and his crew when he agrees to whack an adie-de-camp to Johnny Sack, Joey “Peeps” Peparelli (Joe Maruzzo).

In “Marco Polo,” Tony B. had no business getting involved in the ongoing issue with New York and his choice to whack Joey Peeps inadvertently pulled Jersey into the mess and also led to his mentor and friend, Angelo Garepe (Joe Santos) being killed. At the time, Tony B. is in need of money and feels as though Tony is purposely keeping him from earning a solid living, but in reality, Tony was just looking out for his cousin and trying to keep unwanted attention off him and the rest of the crew. Tony B.’s greed and reckless behavior led to not only one of the most devastating betrayals in the show but also put Tony and the entire crew in danger, all because he wanted to fatten his wallet.

4. Big Pussy Turning FBI Informant

“Funhouse” – Season 2, Episode 13 (2000)

In “Nobody Knows Anything,” detective Vin Makazian (John Heard) informs Tony that his best friend and trusted capo, Salvatore “Big Pussy” Bonpenserio (Vincent Pastore), has flipped and is now an FBI informant. For the remainder of the season, there’s speculation as to the accuracy of this information, but in “Do Not Resuscitate,” it’s revealed only to the viewers that Puss has indeed flipped to avoid an extensive prison sentence for dealing drugs.

Puss’ betrayal is savage and beyond one of the show’s most tragic, which comes fully to light in “Funhouse,” which is easily one of the saddest episodes in The Sopranos. While it was inevitable that Puss would eventually get that house by the shore, that doesn’t mean it still wasn’t a heartbreaking blow. Even though Puss was looking at a hefty sentence, it’s not exactly clear how he ever thought things would work out okay in the end. At least if he hadn’t flipped, he would still be alive and able to see his kids and grandchildren, and Tony and the guys would have taken care of his family. Perhaps doing time would have been too much for Puss, but either way, it still would have been far better than betraying his best friends and leaving his family to pick up the pieces.

3. Christopher Telling Tony About Adriana

“Long Term Parking” – Season 5, Episode 12 (2004)

In “Long Term Parking,” Adriana (Drea de Matteo) comes clean to Christopher and tells him that she has been talking to the FBI, resulting in a heated and physical reaction from Christopher. When Adriana tells Christopher that they can move and start over with the FBI’s help, Christopher agrees, but the next morning, Adriana gets a call from Tony, who says Chrissy tried to kill himself and that he’s sending Silvio to pick her up. Once in the car with Silvio, it’s clear to both her and the audience that Chrissy had a cruel change of heart.

Adriana was the only good and decent person in Chrissy’s life, and even though she should have known better than to talk to the FBI, his decision to choose Tony over her is without question one of the most heartless and brutal betrayals in the show. Don’t get us wrong, Adriana should have lawyered up or at least put on a solid poker face and see if the FBI had put their money where their mouth was, but unfortunately, that didn’t happen. It was obvious that things would most likely not have worked out well for Adriana in the end, but the calculated deception on both Tony and Chrissy’s parts and making Adriana believe that Chrissy tried to kill himself is essentially what makes this betrayal as cold as ice.

2. Tony Killing Christopher

“Kennedy and Heidi” – Season 6, Episode 18 (2007)

After meeting with Phil Leotardo (Frank Vincent), Christopher and Tony are driving back home, but as Christopher’s driving becomes erratic, Tony looks at him, noticing his blank stare and unusual behavior. When Chrissy drifts into the oncoming lane, he quickly swerves the car and ends up driving it off the road and into an embankment. Tony suffers only minor scrapes, but Chrissy is severely injured and tells Tony to call a taxi because he wouldn’t pass a drug test. Initially, Tony begins to dial 911, but after noticing the car seat in the back seat, he hangs up and holds Chrissy’s nose and watches him choke on his own blood (in one of the most shocking Sopranos deaths).

Chrissy has struggled with his addiction to drugs and, as Uncle Junior had previously pointed out, if he weren’t Tony’s nephew, he would have been considered a liability and whacked a long time ago. After getting several generous chances to get his act together, Tony realizes in Kennedy and Heidi,” that his nephew will never change and commits one of the most shocking and brutal betrayals in the entire show. Tony tries to rationalize his choice, believing that Chrissy’s addiction could have harmed his wife and baby, and while that may be partially true, it is more likely that Tony had reached his breaking point with his nephew and seized an opportunity to get rid of him without anyone questioning him.

1. Livia Trying to Kill Tony

“I Dream of Jeannie Cusamano” – Season 1, Episode 13 (1999)

After miraculously surviving an attempt on his life, Uncle Junior tries to play coy while Tony’s mother, Livia, suddenly seems to have issues with her memory. During a therapy session, Dr. Melfi makes the grave mistake of trying to tell Tony that his mother suffers from borderline personality disorder, which causes an intense reaction from Tony. Tony only then realizes that Dr. Melfi was right after he’s approached by the FBI. They have him listen to tape recordings they gathered from wiring Green Grove, revealing to Tony that Livia was the catalyst behind Uncle Junior’s decision to have him whacked.

In “I Dream of Jeannie Cusamano,” Tony not only learns the cold, hard truth about his mother (“she’s a sweet old lady”) but also that she had zero qualms about committing the absolute worst betrayal any parent could do to their child and set him up to be killed. Livia was one of the main sources of Tony’s mental health and overall stress, but despite the strain and exhaustion she caused him, Tony never abandoned her and still tried to do what was right for his mother, which is what makes Livia’s betrayal not only gut-wrenching and unforgivable, but also by far the show’s most brutal.