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The Worst Things Tony Soprano Ever Did On The Sopranos Ranked

Tony Soprano is one of the most enigmatic characters in television history. Every other episode tends to show him justifying his terrible decisions to his therapist, and just when he appears to be making progress in finding healthy ways to cope with his trauma, he performs yet another horrific act in his life. Throughout the whole run of the series, the cycle repeats itself until even the most optimistic fans concede that Tony Soprano will never truly find his way to redemption.

"The Sopranos" is undoubtedly one of the most remarkable programs in television history, and some argue that it ushered in the Golden Age of television. Everything about the drama, from the casting to the writing, has been a shining example of producing a TV show. One of the most significant ways it influenced not just television but also pop culture, in general, was by giving people an indelible taste of how captivating an antihero can be. It's difficult to imagine programs like "Succession," "Breaking Bad," and "Better Call Saul" existing without David Chase's magnum opus.

Tony's brutality was always at the heart of the show. The series went to great lengths to ensure audiences wouldn't become enamored with Tony and his gangster lifestyle. So, in our attempt to deconstruct "The Sopranos" themes, here are the worst things Tony Soprano ever did.

14. Killing Willie Overall

Tony frequently argues with Dr. Melfi that his life in crime was preordained and that all he did was make do with the cards life had dealt him. Tony Soprano was born into a mob family and his parents exposed him to violent criminality as a kid. During one therapy session, Dr. Melfi and Tony experience a breakthrough, finally understanding that Tony's panic attacks happen because he witnessed his father commit horrible crimes and his mother respond to them callously. 

There are also hints throughout the show that life inside the mob isn't always what Tony imagined for himself; before dropping out of college as a freshman, he pondered continuing in school and making a career in sports instead. As an adult, he still has nightmares about his former coach reprimanding him for not focusing on sports. It's evident Tony has a moral compass and, to some extent, regrets not following it.

After quitting college, Tony puts all his effort into being a made man in the mob. He organized a gang of goons with the intention of robbing card games and earning a reputation for himself inside the mafia. Still, Tony can leave this world behind until he commits an irrevocable deed by murdering Willie Overall at age 23. That's when his journey down the dark path truly begins.

13. Disliking Meadow's boyfriend for his race

The portrayal of Tony's family is one of the ways "The Sopranos" distinguishes itself from previous mafia narratives. Unlike in previous mob stories, Tony doesn't even consider having his children succeed him in the mob, favoring a more legitimate path for them from the start. Tony also attempts to conceal his criminal activities from his family, mainly because he's aware that his parents' failure to do so affected him. Meadow, his daughter, is the best example of this progress. Meadow is Tony's first opportunity to end the cycle. Both Tony and Carmela push her to take her schooling seriously and pursue her goal of becoming a pediatrician.

Tony's relationship with Meadow is frequently strained because his attempts to protect her are often overbearing or based on lies, which she does not like. He also isn't shy about expressing his opinions of her romantic life. When Meadow begins dating in college, Tony expresses his bigotry after learning that her boyfriend is partly Jewish and Black. And thus the pattern of emotionally harming the Soprano children continues.

12. Refusing to help Jackie Jr.

Tony's first significant mob operation came when he joined up with Jackie Aprile and two other associates to loot a card game. The deed became legendary among the mob and forged a lasting friendship between Tony and Jackie. 

As Jackie nears the end of his life, he attempts to keep his son, Jackie Jr., away from illegal activities, feeling that he just doesn't have the stomach for it. After Jackie's passing, Tony vows to keep his friend's son out of the business.

Despite this, Tony never makes a point of becoming Jackie Jr.'s mentor, instead leaving that up to Jackie Jr.'s uncle Ritchie, who leads him into minor mob activities. That doesn't last long because Tony's sister kills Ritchie during an argument. Jackie Jr. then falls under the tutelage of an even worse mentor: Ralph. While Jackie Jr. is looking for a father figure, Ralph tells him the famous story of Tony and his father looting the card game, which inspires him to do the same.

It's undeniable that Tony tries to steer Jackie Jr. in the right direction, especially when he begins dating Meadow. Tony recognizes himself in Jackie Jr. and wishes for him to escape this world. But when it really counts, and the Tony-inspired Jackie Jr. card game looting goes awry, Tony doesn't even contemplate protecting Jackie Jr.

11. Serial adultery

Tony's early trauma stems from his acrimonious relationship with his mother, Livia Soprano. (Fun fact: Chase's relationship with his mother serves as the inspiration for the whole series). Livia even once plots to murder Tony because she's irritated by his choice to place her in a retirement facility. Tony has always felt a great deal of self-hatred and shame because Livia makes him feel unlovable.

Still, he always has his wife, Carmela, by his side. "I know you better than anybody, Tony, even your friends," Carmela says at one point, "which is probably why you hate me." And that, in a nutshell, sums up their relationship. Tony despises himself and is embarrassed by Carmela's gaze. As a result, he frequently seeks intimacy with other women, from long-term affairs to one-night stands with sex workers.

There are enough crumbs throughout the series to suggest that Tony's philandering results from his lack of a loving maternal figure in his childhood. He feels that if he could simply find someone other than Carmela to love him, he'll have proven that he is, in fact, deserving of love. At one point, he even falls for Gloria, who embodies many of his mother's worst tendencies. Of course, his indiscretions gradually take their toll on his marriage, and he further fractures his family than he already has.

10. Sabotaging his sister's emotional progress

Tony is an extremely narcissistic individual, as evidenced by several incidents. Some of these incidents are relatively benign and appear to be nothing more than him being petty, such as the time he lashes Zellman with a belt because he's seeing Tony's former mistress. However, his narcissism occasionally goes too far and causes him to damage his closest family members. His behavior towards his sister, Janice, is an example of the latter.

Tony's relationship with Janice is strained and unsustainable, like practically every other relationship in his life. Janice would deny it, but she is pretty similar to their mother. She used to bully Tony as a youngster, and when she's dating Richie, she frequently pushes him to try to oust Tony as the boss. When her argument regarding Richie's son's sexuality gets violent and she murders him, she asks Tony to clean up the scene for her.

Eventually, Janice begins to attempt to change her life. She enrolls in anger management programs and starts learning to deal with difficult circumstances better. Tony becomes envious and, sadist that he is, begins provoking her into losing her temper until she eventually breaks instead of encouraging her growth. In some ways, Tony isn't interested in improving his wounded family; he just wants to gratify his immediate selfish goals.

9. Forcing Bobby to commit murder

Unfortunately, Tony's terrible actions don't end with his family. One example is his handling of Bobby. Bobby is one of the nicest and most loyal people in the entire mob organization. Although he's the son of one of the organization's most violent fathers, Bobby always upholds his altruistic, dutiful character. He never harbors resentment, even when Tony orders the execution of his colleagues. 

That's not to say he's incapable of standing up for himself. However, later in the series, his kindness is misinterpreted as weakness. The boys discover this when Paulie is proven to have withheld money to repair a broken amusement park ride that Bobby's kids rode and that almost killed them. Bobby finds Paulie and confronts him, warning him that he can't endanger his family. By taking such steps, he gradually gains Tony's respect.

Tony rarely expects to be personally challenged since he usually surrounds himself with sycophants who agree with whatever he says. When Tony criticizes Janice, who's now married to Bobby, he doesn't expect Bobby to fight him, let alone win. As a result, he decides to get his retribution by sending Bobby to carry out his first hit, well aware of the consequences to his conscience.

8. Sabotaging Christopher's sobriety

Although Tony constantly romanticizes his father, it's apparent from the flashbacks and his portrayal in "The Many Saints of Newark" that he was never the decent guy everyone remembers him as. Instead, Tony's father was frequently violent and absent. Tony's worst traits can be attributed to striving to live up to his father's legacy. On the other hand, Dickie, Christopher's father, serves as a good example for him. Up to his final day, Dickie never stops trying to influence Tony to live a life free of crime.

You'd think Tony would take Christopher under his wing and keep him out of trouble because of Dickie, but you'd be wrong. Tony first dismisses Christopher's determination to advance in the ranks. However, when Christopher proves himself helpful in executing Tony's nefarious errands, Tony elevates him to the status of a made man. As a result, Christopher's drug addiction begins to spiral out of control as Tony's conferred power compels him to commit more and more horrible deeds.

Once it becomes evident that Christopher can't do his errands effectively, Tony grows angry with his drug issues and forces him to enter treatment to address them. While this first makes it seem as though Tony genuinely cares about Christopher, Tony then starts berating him for staying sober at a party because he thinks Christopher is a party pooper. This eventually leads to Christopher's relapse.

7. Dumping asbestos in a lake

Tony had a pet dog named Tippy when he was a boy; he adored this dog and was devastated when it died. He subsequently discovered that it had been relocated by his father to live with his mistress since Tony's mother, Livia, detested dogs. Tony has had a special place for the animals he meets throughout his life ever since this incident.

Tony often cares for or is delighted by animals; even when Carmela informs him that they have a bear on their property, Tony isn't worried. In fact, there is no time in the show when Tony displays so much outward grief as when his horse dies. The ducks who swim in his pool regularly are one of the most important animals in his life. The fact that the ducks picked Tony's pool as their home fills Tony with pride, as though he has shown to be an exceptional provider and nurturer.

So, while his eventual dumping of asbestos in a lake may not appear comparable to all of the other heinous activities on this list, Tony's willingness to abandon his so-called values when they no longer benefited him is what puts it so high on the list. Worse, you can hear ducks from afar as he dumps the toxic substance.

6. Loan sharking Davey Scantino

Tony first met Davey Scantino in high school. Tony had an incident where Davey came to Tony's help when he needed it most. Davey gradually develops a severe gambling problem as they age. This causes him to incur debts with mob members, one of whom then prohibits him from engaging in any future card games until his debt is paid.

This prompts Davey to approach Tony, not to assist him in repaying his debt, but to partake in another card game. Tony quickly accepts, knowing he stands to benefit. When Davey finds himself owing Tony as well, he attempts to elicit emotion from Tony, recalling their boyhood friendship. Never one to allow empathy to influence too many of his actions, Tony chooses to assault him instead.

Tony takes advantage of the situation even further, first by accepting Davey's son's SUV as payment and attempting to regift it to Meadow, who happens to attend the same school as Davey's son. When his family isn't enthusiastic, Tony decides to push Davey's family business into the ground with his schemes. Tony is a parasite to everyone with whom he has a relationship. His exploits with Davey are a fine example of that.

5. Beating up Georgie

Georgie is a friendly bartender at the nightclub Tony's criminal family frequents. He's mild-mannered and assists the guys with their illegal activities; for example, he helps Christopher move a body and once sweeps the club in search of FBI listening devices after getting word that they're under heavy investigation. Everyone's only issue with him is his peculiar propensity to comment on topics he ought to avoid.

The series makes it clear that Georgie displays signs of having an intellectual disability. This doesn't prevent the guys from batting him around any time he says anything they'd prefer not to hear at the time. However, there's one particular instance in which Tony experienced stress unrelated to Georgie. Later, he's upset that Georgie is discarding partially melted ice because he thinks it's a waste of resources. When Tony rhetorically asks Georgie if he thinks ice grows on trees and Georgie replies that he doesn't, Tony then reacts angrily, attacking him with an unusual degree of intensity.

This is particularly disturbing as it demonstrated Tony's willingness to assault vulnerable people. Violence is an outlet for Tony's anxiety and suppressed emotion, and it sometimes winds up directed at the nearest person, not just those who mistreat him. 

4. General abuse of AJ

Tony comes from a household where affection was uncommon and mostly expressed with material goods. Tony takes these lessons with him into maturity and fatherhood. Unfortunately, this proves inadequate for Anthony "AJ" Soprano Jr. Tony is rarely available to guide AJ, and when he is around, he's not exactly the best role model.  

AJ begins acting out at a young age by crashing his mother's car, cheating on exams, and generally disregarding his school's standards. Tony's response is to send him to military school, but he changes his mind when he finds AJ suffers from panic attacks as well. Tony's main objective is to create a better life for his children than he had in the mafia. However, Tony's approach to doing this is to spoil his kid. When AJ shows signs of a lack of purpose in life because of this, Tony severely punishes him. This cycle continues throughout the series.

Tony fights his son when he's disobedient, but doesn't instill real discipline, only fear. Instead, he wishes to reap seeds he's never sown. In the show, AJ frequently sinks into depression, and Tony's answer is usually to make it about himself and how it makes him feel rather than genuinely caring for his kid.

3. Having Silvio kill Adriana

Adriana was already used to the mob life when Christopher started dating her, having grown up as a member of the Aprile family. While it initially appears that she cares for Christopher only because of all the material comforts he could provide, she gradually shows that she genuinely loves Christopher and helps bring stability to his life.

When Tony assassinates Sal "Big Pussy" Bonpensiero, the FBI is left without an informant connected to the crime family. They regard Adriana as someone they can potentially use as a new rat. Adriana is forced to comply partly as a consequence of a chain of unfortunate events that begins with the FBI sending an undercover agent to Adriana and concludes with the agent discovering that Christopher's a heroin addict and threatening to tell Tony, which would undoubtedly destroy their relationship. Adriana's situation further deteriorates when the FBI discovers that she's dealing narcotics out of her club. The FBI demands complete cooperation or they'll prosecute her.

Adriana chooses to tell Christopher the truth and suggests they flee together. Instead, Christopher tells Tony, who demands to know how much she told the FBI. Tony has worked with the FBI on multiple occasions and knows this might not be as bad as it seems. Regardless, he directs Silvio to assassinate Adriana right away without further investigation.

2. Gambling away the money he pledged to helping Vito's family

Tony becomes increasingly malevolent as the series progresses, and nothing exemplifies this more than his treatment of Vito's family following his death. Vito is a faithful member of their crime family until he's outed as gay, at which point Phil decides to assassinate him. While Tony disagrees with such an extreme approach, he isn't one to intervene in matters that don't directly affect him. Vito's brutal murder, on the other hand, has a significant impact on Vito Jr., who endures a major personality shift and becomes self-destructive.

In the episode "Chasing It," Vito's wife contacts Tony and requests $100,000 to relocate and start afresh, believing that this will benefit Vito Jr. This happens at a bad moment; Tony has already accumulated other debts and is battling gambling addiction, despite having looked down on gamblers his whole life. Throughout the episode, Tony prioritizes his selfish hobbies over paying off his debts and supporting Vito's family.

Tony eventually loses all his money and decides to extort his wife for more. Instead of repaying his debts and providing for Vito's family, he ultimately returns to gambling. Eventually, the little money he has left isn't enough to support Vito's family, so he merely offers to send Vito Jr to a tough love camp in Idaho.

1. Killing Christopher

Christopher's father was the only positive parental figure Tony had as a youngster, so Tony feels responsible for Christopher. However, Tony never learned how to adequately care for those he loved, so he was never present during Christopher's childhood. Instead, Christopher grew up with an alcoholic mother, no father, and plenty of ties to the criminal underworld. He never really stood a chance of escaping a life in the mob. 

Tony only becomes a father figure to Christopher once he's rising through the ranks of their organized crime enterprise. Christopher would do anything to please Tony and prove his loyalty. They have a strong relationship, at least by mafia standards. However, when Christopher's work impinges on his conscience, he begins to abuse drugs and flirts with a career in a more legitimate field.

Christopher's mafia colleagues are, of course, terrible influences. Tony berates him for wanting to stay sober, while Richie tells him that beating up his girlfriend Adriana is appropriate only if they're married. When Christopher ultimately has a car accident with Tony in the car while high, Tony decides he can no longer trust him, which means he must murder him. Tony then convinces himself that everyone will be glad his mentee Christopher is no longer a burden to anyone else. That's when Tony fully demonstrates his true evil.