Top 10 Worst Things Tony Soprano Ever Did
#10: Executing Salvatore Bonpensiero “Funhouse”
In Tony’s world, loyalty is not an option. So, when he finds out that one of his associates has been talking to the FBI, his only path is to take him out. This situation is complicated by the fact that the snitch is his close friend, Salvatore Bonpensiero. Upon discovering a wire at Salvatore's house, Tony lures him out to sea and executes him with fellow crew members Paulie Walnuts and Silvio Dante. It might have been hard for Tony to do, but if Salvatore was truly his friend, he wouldn’t have done it.
#9: Setting Silvio on Matt Drinkwater “The Happy Wanderer”
Tony doesn’t just do cruel things to people; he seems to delight in causing misery and discomfort. At a high-stakes card game, he decides to have cruel fun at the expense of Matthew Bevilacqua, a.k.a. “Matt Drinkwater,” an underling of Christopher. During the game, Tony instructs Matt to sweep up some crumbs, particularly the ones underneath Silvio. The pressure has clearly been getting to Silvio, and he explodes right when the sweeping starts. Tony looks on, not even trying to suppress his glee at the situation he's created, which also inspires a new nickname for Matt.
#8: Making Bobby Whack Someone “Soprano Home Movies”
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Tony has power and an incredibly fragile ego. So, if you make him mad, he can make you do some terrible things as revenge. In this final season episode, Tony and Carmela celebrate his birthday at the upstate New York cabin of his sister, Janice, and her husband, Bobby Baccalieri. A physical altercation breaks out between Tony and Bobby during a game of Monopoly, and it’s not a matter of “forgive and forget.” Earlier in the episode, they discussed Bobby had never actually whacked someone in his time as a gangster. So, Tony tasks him with a hit, which he can't turn down. At least we got to see Bobby serve Tony with a well-earned beatdown.
#7: Mocking Chris’ Sobriety “Cold Cuts”
Tony will blast you if you have issues, and if you try to change, he’ll do everything he can to sabotage you. When Christopher Moltisanti quits drinking and using drugs, Tony, who routinely chastised him for his vices, refuses to respect his getting clean. During a steakhouse dinner with Tony Blundetto, the two Tonys start incessantly teasing Chris about his sobriety. When Chris protests his treatment, Tony goes on the defensive. In the very same episode, he mocks Janice for her estranged relationship with her son, when she had been working on her anger issues. To know Tony Soprano is to know toxicity.
#6: Whacking Tony Blundetto “All Due Respect”
The arc of Tony Blundetto, played by Steve Buscemi, is one of the show’s most tragic. Paroled from prison, after serving nearly 17 years for a robbery Tony Soprano was also supposed to take part in, Tony B attempts to go on the straight and narrow as a massage therapist before falling back into a life of crime. His recklessness makes him the target of influential Lupertazzi family member Phil Leotardo, and Tony knows his cousin is marked for a slow and painful death. Tony at least lets Tony B die in a relatively merciful way, but this still shows how numbed he is to this world of brutal murder.
#5: Ordering Bobby Sr. to Whack Mustang Sally “Another Toothpick”
Years before Tony makes Bobby Jr. whack someone, he makes the same request of his father. After Bobby Sr.'s godson, Sally Intile, a.k.a. "Mustang Sally," attacks Bryan Spatafore, leading to a coma, he's marked for death. Tony decides as godfather, Bobby Sr. is the man for the job. This is especially cruel because Bobby Sr. is stricken with lung cancer, and Tony refuses to honor Bobby Jr. or Uncle Junior's requests to let him off the hook. Bobby Sr. completes the hit, but on the drive back, he starts violently coughing and crashes, resulting in his death. Tony doesn’t have to brandish any weapons to be responsible for people’s deaths.
#4: Intimidating Meadow’s Boyfriend “Proshai, Livushka”
It comes as no surprise that Tony holds extremely prejudiced views towards other races and cultures. But his internal ugliness truly comes out when he first meets Meadow’s boyfriend Noah, a Columbia student who’s half-Black and half-Jewish. As soon as Meadow leaves, Tony starts to needle Noah about his heritage and eventually instructs him to stay away from his daughter. Tony makes absolutely no attempt to hide his bigotry, and Noah responds with two words that few people have the guts to say to Tony Soprano. Meadow and Noah didn’t last, and Tony’s interference certainly didn’t help matters.
#3: Forced Adriana La Cerva’s Murder “Long Term Parking”
Anyone who is a threat to Tony Soprano is in grave danger; it doesn’t matter if they’re basically a civilian. When Chris’ fiancée Adriana, played by Drea de Matteo, reveals to Chris that she's been working with the FBI, he turns on her, telling Tony about her betrayal. He arranges to have Silvio pick her up and take her out, under the pretense of them seeing Chris in the hospital. It’s truly heart-wrenching to see Adriana realize what a terrible situation she has gotten herself into and how she can’t get out, and Tony once again puts his safety over the lives of others.
#2: His Extramarital Affairs Various Episodes
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Tony believes in loyalty, but only if it means other people being loyal to him. Throughout the series, Tony had various mistresses or “goomahs” who he’d see behind his wife, Carmela’s, back. While she acknowledges his infidelity, it’s evident how much it hurt her. And when a spurned former lover calls and tells her about their affair and another, between Tony and her cousin, she’s so incensed, she ends up kicking Tony out of the house and planning for divorce. Even after they reconcile, Tony still continues to cheat. He’s either incapable of understanding what it means to be faithful, or he simply doesn’t care.
#1: Christopher’s Death “Kennedy and Heidi”
If Christopher Moltisanti had grown up under different circumstances, he might have had a healthy, happy, and peaceful life. But with a mentor like Tony Soprano and a taste for drugs and alcohol, he had really no chance. When Chris is driving them home one night, he rolls over his car, which Tony escapes with minimal damage. However, Chris tells him to not call an ambulance since he wouldn't be able to pass a drug test. Realizing just how much of a threat Chris is to his business and how much danger Chris could put his infant daughter in, he suffocates him and claims that he died from the wreck. In Tony’s sick mind, causing someone’s death is the same thing as saving them.
