The Sopranos was always more about psychology and philosophy than it was about the traditional violence and excitement of mob stories. It featured complex characters and complicated relationships that explored generational trauma, modern society, and human nature. Those who tuned in solely for the mafia intrigue and murders missed some of the best and most important elements of the series. Still, that doesn’t mean the show didn’t have some great moments of backstabbing and truly memorable betrayals.
Over six seasons, more than a few characters met terrible ends or faced terrible danger at the hands of those they considered friends. Not every betrayal ended in death, but they all left one character worse off and often questioning life. While The Sopranos made clear that mistrust and duplicity were the norm in the world of the mafia, many betrayals still surprised both characters and viewers, leaving them wondering what would come next. Among these moments, a handful still stick in the minds of fans long after the series’ finale.
10. Tony’s Mistreatment of Hesh Marked a Turning Point for his Character
The Sopranos Season 6, Episode 16, “Chasing It”
HBO
Tony knew Herman Rabkin for most of his life. The music producer and loan shark had worked with his father and was his friend, later forming the same relationship with Tony himself. From the beginning of the series, the pair were close, with Tony valuing Hesh’s business insights and even confiding in the man when he didn’t have access to a therapist. Given this history, it was surprising to fans and revealing of the mob boss’s downward spiral when he turned on his friend over a loan.
In Season 6 Episode 16 “Chasing It,” Tony developed an addiction to gambling and lost more and more money. Needing to cover his losses, he turned to his friend Hesh but, rather than using the money wisely, continued to burn it on losing bets. When Hesh politely and respectfully asked Tony to pay him back, it created a rift in their relationship. Tony began mocking Hesh publicly and making antisemitic remarks. All of this marked a shocking betrayal of a close friend and signaled the degree to which Tony was losing control of himself by the end of the series.
9. Tony’s Many Affairs Became Accepted but Still Hurt Carmela
The Sopranos Season 4, Episode 13, “Whitecaps”
HBO
In The Sopranos, made men having mistresses (goomars) was accepted and even expected within their culture. Nearly every male character regularly cheated and Tony was no exception. Over the course of the series, he had serious relationships with several different women and more than a few casual flings. While he saw this behavior as normal and Carmela largely tolerated it, it was still a betrayal of his wife, his supposed morals, and the religious beliefs he claimed to hold.
These betrayals were an open secret for Tony and, while Carmela came to accept this aspect of his life, it never stopped hurting her. These affairs nearly ended their marriage when Irina, angry at Tony for breaking with her, called his house and spoke to AJ and Carmela. For Carmela, part of the betrayal was the affair itself, but part of it was Tony’s inability to keep it secret, forcing her to confront the reality directly. The status quo was eventually restored, but the betrayals never actually ended.
8. Paulie Leaked Info About Tony’s Crew to Johnny Sack
The Sopranos Season 6, Episode 15, “Remember When”
Image via HBO
One of the primary rules in the mafia is that secrets are to be kept within the family. Talking to outsiders, even other families, is a serious crime that can carry deadly consequences. Paulie violated the principle by sharing gossip and even important business information with Johnny Sack, the underboss of one of the New York families. Motivated by Paulie’s frustration at being in prison and feeling that he wasn’t receiving the support he deserved, his role as an informant continued after he was released, costing Tony money and nearly costing lives.
The most infamous instance of Paulie’s ongoing betrayal was revealing the offensive joke Ralph Ciffaretto told about Johnny’s wife, leading to a few that nearly ended with both Ralph and Johnny being killed. Other information was spilled, including some of Tony’s money-making schemes he was trying to hide from New York, which further increased tension between the two families. Paulie remarkably got away with his betrayal, but it was a close call for him and for several other people.
7. Ray Curto Successfully Informed on Tony for Years Before His Death
The Sopranos Season 6, Episode 1, “Members Only”
Image via HBO
Even worse than speaking outside the family is speaking to law enforcement. While, by the end of The Sopranos, several characters had cut deals with the FBI and informed on Tony, Ray Curto’s betrayal was truly shocking for how successful he was at hiding it. The New Jersey family captain was revealed to be an informant early in Season 3 and was regularly shown meeting with FBI agents and displaying no guilt, internal conflict, or even fear about what he was doing. By the end of the series, Curto was one of the greatest threats to Tony, and it was only sheer luck that saved him.
In the Season 6 premiere, “Members Only,” Curto unexpectedly dies of a stroke while sitting in an agent’s car. This death likely saved Tony, at least for a time, and meant the treasonous captain took his secret to the grave. By the end of the series, no one outside the FBI knew about this betrayal, but it was amazing both in its scope and its brazenness. Arguably what makes it even more memorable is that it’s never revealed just when or why Curto turned on Tony, making it one of the enduring mysteries of the show.
6. Dwight Harris Betrayed His Oath and His Principles
The Sopranos Season 6, Episode 1, “Members Only”
HBO
For much of The Sopranos, agent Dwight Harris was the face of the FBI team chasing Tony and his crew. Regularly directing operations designed to gather evidence and gain informants, Harris even met with Tony face to face frequently, with the pair verbally sparring. Later, the agent was transferred to a team working on counter-terrorism, a reaction to the 9/11 attacks, and he was out of Tony’s life for a time. When he returned to New Jersey, Harris reconnected with Tony and often tried to get the mobster to help him with his investigations into terrorism. It was during this time that Harris lost sight of principles and betrayed his oath.
While their later relationship seemed to originally be based on Harris wanting information from Tony, the FBI agent later seemed to develop a fondness for the man. Multiple times, Harris gave the mob boss warnings, revealing Bureau secrets about investigations into other mafia families. By the end of the series, he was even shown celebrating when Tony had Phil Leotardo killed, winning the war between their families. Harris may not have switched teams, but he certainly betrayed his principles and the oath he took when he joined the FBI in supporting a violent criminal and taking pleasure in his success.
5. Tony Murdered His Own Cousin, Tony Blundetto
The Sopranos Season 5, Episode 13, “All Due Respect”
Image via HBO
Tony carried guilt surrounding his cousin, Tony Blundetto, from the moment he was released from prison. A panic attack, something that was already a source of shame, prevented him from joining Tony B. on the job that got him arrested. Embarrassment and the survivors’ guilt left the New Jersey boss struggling to cope and build a healthy relationship with his cousin when his sentence ended. Arguably, it was these feelings that prevented Tony from intervening when his cousin clearly started losing control and endangering the family’s relationship with New York.
When Tony B. gunned down Phil Leotardo’s younger brother, it set off a series of events that ended with Tony murdering his cousin for the sake of peace with New York. To his credit, Tony tried to protect his cousin for some time after the incident, refusing to give him up to New York and risking the rest of the family. In the end, he may have done Tony B. a kindness by giving him a quick death, far better than what he would have received at the hands of Phil. Still, Tony’s murder of his cousin was a memorable moment, ending and dramatic character arc in the most violent and definitive way possible.
4. Junior Ordered a Hit on Tony in the Very First Season
The Sopranos Season 1, Episode 9, “Boca”
Image via HBO
Tony’s relationship with his uncle Junior was, at least, as complicated as his relationship with his cousin. A father figure, Junior still knew how to push Tony’s buttons and was too proud to ever let his nephew rise above him in the family’s hierarchy. When acting boss Jackie Aprile died, it was apparent that a conflict between the pair was inevitable. Still, it was shocking how far Junior was willing to go to ensure he remained the head of the New Jersey outfit.
Junior’s ordering of a hit on Tony was a turning point for the two characters and led to events that set the stage for the rest of the series. The attempted assassination snapped Tony out of his depression, if only briefly, and sparked his official move to take control of the family. Junior’s decision, and the attack itself, are still some of the most memorable moments of the series, establishing the tone and themes of the entire series.
3. Big Pussy Became an FBI Informant
The Sopranos Season 2, Episode 13, “Funhouse”
HBO
Big Pussy was Tony’s best friend and one of his oldest in the family. The two rose through the ranks of the family together and Tony even made Pussy his son’s godfather. If there is one person Tony would likely have trusted implicitly, it was his old friend. So it took him so long to realize and consciously confront the truth. While questions about Pussy’s loyalty were raised in Season 1, it wasn’t until Season 2 that the facts were revealed.
The gangster had turned on his family before the show even began. This betrayal was easily one of the biggest of The Sopranos. Big Pussy was a main character and had been a major part of the series from the very beginning. The fact that someone so important could be an informant spoke to how precarious Tony’s life was and the fact that he couldn’t truly trust anyone. Years later, this betrayal continued to haunt the mob boss and inform his decisions.
2. Tony Murdered His Nephew After Their Car Crash
The Sopranos Season 6, Episode 18, “Kennedy and Heidi”
Image via HBO
One of the most dramatic deaths in the series was disturbing for how subdued it was. After a violent car crash, Tony looked into the face of his nephew. A man he had seen as a son, but now a burden and liability, he decided in that moment to take his life rather than save it. The act itself, suffocating Chris as he stared up, unable to move, was horrific while also quiet. It was a terrible moment in the show and one of Tony’s most horrible betrayals.
What made this murder even more shocking was the fact that Tony showed no remorse after the fact. Though exhibiting the characteristics of a sociopath throughout the series, Tony still seemed capable of feeling guilt at some of the horrible things he’d done. Many of his murders haunted him years later. With Chris, however, it was only relief that Tony appeared to feel. The betrayal was awful, but the aftermath was even worse.
1 Chris Set Up His Own Fiancé to Be Killed
The Sopranos Season 5, Episode 13, “All Due Respect”
Image via HBO
Chris was ultimately at the center of The Sopranos’ two most memorable betrayals. Before he was eventually killed by Tony, the gangster betrayed his fiancé, Adriana, setting her up to be gunned down by Sylvio. When the woman he claimed to love finally revealed she had been informing the FBI and begged him to join her in Witness Protection, it briefly looked like he would leave the life and follow her into exile.
Instead, to the surprise of the fans and Adriana, he reported to Tony, letting him have her murdered so he could remain a mobster. The turning point for Chris was seeing an average man with an average family at a gas station. Faced with the prospect of becoming a regular guy, he instead decided the excitement of being a gangster was most important to him. Betraying Adriana for the sake of money and thrills was easily the most stunning act in the show and led to one of its most memorable deaths.
