The Sopranos: 5 Times Tony Was A Genius (& 5 When He Wasn’t)

Before Walter White or Don Draper were even a glimmer in their creator’s eye, Tony Soprano was running the mob in New Jersey. Early in the series, The Sopranos establishes Tony as a sympathetic character – a man with a manipulative mother that suffers from panic attacks and chronic depression.

But as the series peels back more of Tony’s character, the audience sees him for what he is, which is not even an anti-hero but a flat-out villain. Over six seasons, Tony made plenty of pivotal decisions. Here are five situations where he was a criminal genius and five others that he’d probably like to do differently if he could.

Genius: Making Uncle Junior the Official Boss of the New Jersey Family

With the death of Jackie Aprile Sr. in Season 1, the DiMeo (Soprano) crime family was left without a boss. Since Aprile failed to name a successor, Tony and his uncle were left to squabble for control. But with perhaps his biggest stroke of genius in the entire series, Tony concedes power to his Uncle Junior because he knows he’ll be able to manipulate him behind closed doors.

With Uncle Junior the official boss of the family, the FBI also wouldn’t be as focused on indicting Tony. Tony had to swallow his ego to give Uncle Junior the official title of boss, but things worked out the same as if he were the true boss, and Junior was forced to give away his title to Tony as his health deteriorated.

Not Genius: Giving Away Richie Aprile’s Leather Jacket Gift

Tony and Richie had plenty of issues during Season 2, but as a sign of respect, Richie gave Tony a beautiful leather jacket he obtained years ago from another mob boss. Tony accepts the gift but then later, Richie finds out Tony gave the jacket to the maid’s husband. Obviously, Richie resented Tony giving away his gift, and their relationship wasn’t the same again.

It would have been much smart of Tony to just throw the leather jacket into his closest and never wear it if he didn’t like it. Tony had to have known Richie wouldn’t like him not keeping it.

Genius: Hiding Weapons & Cash at his Mother’s Nursing Home

It’s a retirement community! Whatever you want to call it, Tony needed a safe place to hide his weapons and cash to avoid trouble with the FBI. What better place to hide those incriminating materials than at an old person’s home?

Tony’s associates and friends found this to be such a good idea that they also placed their mothers in homes and began hiding the items they weren’t supposed to possess in the closets of their mother’s new places. Retirement communities in New Jersey aren’t cheap, but at least Tony got a two-for-one deal.

Not Genius: Dating a Woman He Met in Therapy

There’s plenty of normal, everyday people who need therapy to care for their mental health. However, it’s also probably not the best place to pick up a woman. As it turns out, the woman Tony meets at therapy, Gloria Trillo, is suicidal, but he doesn’t know this before beginning an affair with her.

After Tony wants to end their relationship, she threatens to tell Carmela and his children about the affair to try and convince Tony to continue their relationship. That’s not exactly the kind of thing a mob boss is going to love. Of course, the smartest thing Tony could have done would have been to not meet women anywhere and stay loyal to his wife.

Genius: Taking advantage of his Old High School Friend’s Gambling Problem

There’s a reason why Tony rose to mafia boss. He’s a shrewd businessman that’s so ruthless that he even views the weaknesses of his friends as an opportunity to make a score. After getting reacquainted, his childhood friend, Davey Scantino, asks Tony to play in his high stakes “executive” poker game. Scantino is desperate for money, as he owes Richie Aprile $8,000.

At first, Tony tells Scantino, no, but then he relents. This leads to Scantino falling $45,000 into debt to Tony. Tony appears sympathetic to his old friend’s problem at first, but then he seizes all of Scantino’s merchandize at his sporting goods store. Scantino’s life is left in ruins.

Not Genius: Sleeping with Ralph Cifaretto’s Ex-Girlfriend

After ending things with Trillo in Season 3, Tony meets the Cifaretto’s goomah (mistress), Valentina La Paz, at the horse stables. They sleep together, but Tony declines to want to see her again because she is dating his work associate.

La Paz continues to pester him for another date, though, and she then reveals to Tony that Cifaretto leaves her sexually unsatisfied because of unusual fetishes. As if that makes it alright, Tony begins an affair with La Paz. This gets him in trouble both at home and at work because Cifaretto and Carmela each find out about Tony’s latest transgression.

Genius: Holding a Consultation with Every Worthwhile Lawyer in New Jersey during his Divorce

No one said being smart was the same as playing clean. Tony gets downright nasty after his wife, Carmela, asks for a divorce. He places her on an allowance and spoils his son, A.J., with gifts, so A.J. will side with him. But Tony’s biggest act of evil (or genius) during his separation with Carmela was holding a consolation with every high-end divorce lawyer in northern New Jersey.

This leaves Carmela without a way to sue him for any money should she follow through with the divorce. Without anywhere to turn – Carmela also learns the hard way no man will ever consider a relationship with the former mob boss’ wife – she is forced to accept living a normal, middle-class life or return to her marriage with Tony. Carmela chooses the latter.

Not Genius: Finding himself in a Room Alone with Adriana

Tony nearly kisses Adriana when they are alone in the back room of her club, but two New York mobsters arrive for a meeting and interrupt them before anything can happen. A few nights later, Tony finds himself in the same situation, alone with Adriana late at night at the club. This time, nothing sexual happens, but they get into a bad car accident on the way to buying cocaine.

That leads Christopher and everyone in the family to suspect Tony and Adriana were having an affair. While Tony was actually not guilty of cheating in this case, there’s no telling what Tony and Adriana would have done while high on cocaine together. Tony was stupid to put himself in that situation.

Genius: Gaining a House for His Sister in a Trade from Johnny Sack

Finally in season six, Tony puts his business genius to good use for someone in his family. In jail, Sack needs his share of a business company he owns one-third of, so he asks Tony to tell his two business associates to sell the company.

Tony leverages the situation, telling Sack that he’ll convince the two business associates to sell if Sack sells his mansion to his sister, Janice, and her husband, Bobby, at a discounted rate. Without any other options, Sack agrees. This is another example of Tony taking advantage of a friend in need, but throughout the series, Tony treats Janice will malice. This is one of the few examples where he puts someone other than himself or his immediate family first.

Not Genius: Failing to Move Uncle Junior into a Nursing Home

Tony forced his mother into her “retirement community” before she was ready, but he doesn’t do the same to Uncle Junior at the beginning of Season six. He nearly pays for that decision with his life. While watching Uncle Junior one day because no one else was available to do it, Tony cooks him dinner, but his deranged uncle doesn’t realize who he is and shoots him in the stomach.

Tony barely stays awake long enough to dial 911 before passing out. Tony does recover from the bullet wound, but the pain and suffering could have been easily avoided had Tony made the right decision and dealt with his guilt of placing Uncle Junior in a home.