The Sopranos

The Sopranos: 10 Saddest Things About Tony

Tony Soprano is perhaps one of the best anti-heroes in television history. Fans of the show both love and hate him, as he's a flawed but very sad man.

The title of TV’s greatest antihero is a highly contested one, but DiMeo crime family boss Tony Soprano definitely ranks highly. At the top, he battles it out with characters like Walter White and Jax Teller. Tony is nowhere near perfect and the list of his sins would impress the devil. But fate isn’t so kind to him either. These factors make audiences both hate and pity him at the same time.

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Before The Sopranos came along, TV shows and movies only focused on the golden age of the mafia. The HBO hit series handles things differently by telling the story of a highly-flawed mobster in a modern setting.

His Strained Relationship With His Mother

The Sopranos Tony and Livia

Tony cannot be blamed for his strained relationship with his mother, Livia. It’s revealed that she had always been an abusive mother and wife who stressed out her children and husband. Despite Tony trying to help her in her older age by putting her in a retirement community, she detests him and suggests that he is trying to lock her up.

She even tries to get Tony killed twice, first by persuading Uncle Junior to do it, and then by telling Artie that Tony blew up his restaurant. After her stroke, Tony ignores her completely and cuts off all financial support.

Extramarital Affairs

Tony and his mistress Gloria Trillo kiss inside her apartment in The Sopranos

If there is one thing Tony doesn’t know how to do, it is staying faithful to his wife, Carmela. Over the course of their marriage, the mobster cavorts with several mistresses. Carmela is aware of his infidelity, but she chooses to stay because of the kids and because of the lifestyle he provides her.

His lustful ways almost get him into trouble when he begins dating the car salesperson, Gloria Trillo. Despite initially appearing to be more responsible than Tony’s other lovers, she grows obsessed and threatens to tell his family if he leaves her. Tony is eventually forced to use his men to threaten her in order to get her to back off. Sadly, she commits suicide.

Uncle Junior Is A Constant Pain In His Neck

Junior warns Tony not to get too comfortable in The Sopranos

One thing that makes Tony look weak is his failure throughout the series to take care of the “Uncle Junior” problem. Junior gives Tony headaches, but Tony never takes any serious action against him. This is surprising, considering that he always whacks anyone else who tries to get in his way.

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Perhaps Tony is lenient because Junior is family. But despite the fact that they are related, Tony ought to have realized early on that letting Junior live was dangerous for him. The two mobsters clashed too often and things almost turned tragic when Junior accidentally shoots him, later in the series.

The Therapy Sessions Are Complicated

Dr Melfi and Tony Soprano in The Sopranos.

Tony’s therapy sessions aren’t as straightforward as he’d like them to be. First, he tries to keep it a secret because he fears he’ll lose respect if his fellow mobsters found out he was seeing Dr. Melfi. They find out eventually and he’s forced to open up about it.

Tony also has a crush on Dr. Mefli, but she’s the one woman he never gets. At times, it feels like the two will hook up, but it never happens. He tries to get another therapist, but he’s rejected because the therapist doesn’t work with criminals. Eventually. Dr. Mefli cuts ties with Tony after being convinced by a colleague that she was enabling him.

A.J. Constantly Stresses Him Out

Big Pussy gives AJ advice about adolescence in The Sopranos

A.J. Soprano is a difficult character to like because he never does anything to make anyone proud. Not only does he keep getting into trouble, but he’s also poor in class and he lacks any form of ambition.

A top mobster like Tony would have loved it if his son was involved in the family business too, but A.J. just isn’t cut out for it. He is lazy and entitled, but Tony shoulders part of the blame for this. He is never really as tough on him as he is to his subordinates and he doesn’t mentor him either.

Incidences Of Racism

Tony and Noah

The show constantly hints that Italian Americans are discriminated against by the American justice and immigration system. Given that he is part of a community that is targeted, Tony should know better than to be racist. But this isn’t the case. There are several moments when he shows disdain against Black people.

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When Meadow starts dating a Black boy named Noah, Tony isn’t too pleased. When Noah shows up at the house, Tony pulls him aside and threatens him. Another incident occurs when he’s driving around with A.J. showing him his Italian heritage and he insults a pair of Black men.

He Ironically Makes Fun Of Chris And Janice For Trying To Be Better

Christopher drives Tony to a meeting with Phil in The Sopranos

Tony relies on motivation from a therapist, but he treats other people taking similar actions unfairly. Janice begins attending anger management therapy sessions in order to improve her domestic life, only for Tony to mock her. He sees it as a joke and even makes fun of her during dinner.

Then there is Christopher’s case. The young mobster attends rehab for his alcoholism, but Tony makes fun of him for drinking soda. He encourages him to drink, thus getting him addicted even further. Ironically, the same Tony later kills Christopher for failing to control his alcoholism and drug addiction.

The Shooting Incident

Tony Soprano in the hospital

In the season 6 episode “Members Only,” Junior mistakes Tony for Big Pussy and shoots him in the abdomen. Even though Tony survives, the incident derails him.

He remains in a coma for a couple of days, during which time he has strange dreams. While he is in the hospital, some of his subordinates try to undermine him because they believe he will die. When he finally recovers, Tony has a tough job of reasserting his dominance. He goes as far as to fight his bodyguard just to prove he is still tough.

Disrespect Towards His Juniors

Richie gifts Tony Rocco DiMeo's jacket in The Sopranos

Tony doesn’t care much about his juniors, and this tends to create problems for him. When Richie gives him a jacket as a gift in season 2, Tony gives it to the maid’s husband. As expected, Richie finds out and this puts a dent in their relationship.

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In season 3, Tony begins an affair with Ralph’s ex-girlfriend, Valentina La Paz. He initially vows to stop seeing her after finding out about her relationship with Richie, but when she confesses that Ralph doesn’t satisfy her in bed, Tony pushes to resume the affair. Worse still, he later murders Ralph.

He Could Have Had A Different Life

Tony strangles a witness who had gone into witness protection

Despite the fact that Uncle Junior constantly mocks him by stating that “he never had the makings of a college athlete,” Tony could have indeed had a ‘clean’ career in sports had he not dropped out of college to pursue a life of crime. That would have been better than him constantly watching over his back and having to kill people.

During a dream sequence, Tony met his highschool football coach, who chastised him for quitting sports to become a criminal. The coach told him that he could have even succeeded. Since Tony’s dreams mostly stemmed from his fears and regrets, it can be argued that he really desired a legitimate life, at some point.

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