Ranking Tony Soprano’s Worst Business Decisions

When you hear the words “mafia boss,” the first thing that comes to mind probably isn’t “diverse business portfolio.” Yet, Tony Soprano (James Gandolfini), acting boss of the DiMeo crime family and central character on The Sopranos (available to stream anytime on HBO Now), saw his empire grow substantially over the course of the show’s six seasons. Still, as an impatient man with very little impulse control, he inevitably made some terrible decisions that ended up costing him more in the end. With that in mind, here’s a ranking of some of Tony’s worst business decisions.

7. Selling Off Some Real Estate

“The north ward is the north ward,” Tony tells Julianna (Julianna Margulies), a broker who’s been eyeing one of his business properties on behalf of the Jamba Juice corporation. At first, he bluntly explains he’s not interested (in selling his building) despite her nudging reminder that he’s a business man. Still, Tony refuses to bend, citing the importance of community over a financial gain before mentioning how everything in America was starting to look, in his words, “the f*cking same.” Whatever happened to Gary Cooper, right Tony?

His noble intentions toward his old neighborhood aside, he eventually relents and sells, mostly as an opportunity to hurry his chances at sleeping with Julianna. Then, just as the champagne had been poured and the papers had been signed, Tony thinks back to his wife, Carmela, and abruptly bails on the whole situation. He later tries to rekindle his chance at having an affair, but isn’t able to do so, which leaves him with hurt feelings, a gentrifying neighborhood, and about half a million in cash. That last part makes this sound like a pretty decent deal, but if Tony had waited till a few more businesses had come to town, he could have gotten a better price. That’s why this is last on the list.

6. Borrowing Money From Hesh

This isn’t so much a business problem as a lifestyle problem that impacts his business, specifically, his near constant gambling. As family associate Hesh (Jerry Adler) explains to his son-in-law Eli (Geoffrey Canto), a big part of his income comes from gambling, and practically living in that environment leaves Tony in need of money whenever he’s had a particularly bad run. It’s during one of these bad runs that he asks for a bridge loan from Hesh, to the tune of $200,000.

While the notion of lending money to a friend is already a dicey proposition (and one that will come up later on this list), Tony makes the situation worse by constantly chastising Hesh over the debt. It starts with passive-aggressive remarks about paying points against the principal but gets so bad that it pushes his friendship with Hesh to the brink. It also affects his home-life, as Tony tries to convince Carmela to put up money of her own on a bet he sees as a surefire win, pushing him to completely lose it when it doesn’t go his way.

5. Making Gigi A Captain

Ralph (Joe Pantoliano) may have been one of the most despicable characters in Sopranos history, but in the beginning, he was desperate to impress Tony and wanted recognition by being made captain over the Aprile crew. Tony, who hated Ralph more than most people, refused to give him the position, even though Ralph really did deserve it, based on what he earned for the family. Instead, Tony gave the position to Gigi Cestone (John Fiore), a well-respected soldier, but one who wasn’t ready to deal with Ralph as a subordinate.

Tensions continued to mount between Tony and Ralph, forcing Tony to wrestle with the idea of demoting Gigi, even though doing so would make him look weak and indecisive. Ralph, meanwhile, used the opportunity to talk trash about Tony to the crew whenever Gigi was absent, giving Tony cause to worry about a possible mutiny. In the end, Gigi’s fatal heart attack on Thanksgiving ends up solving the problem, which allowed Ralph to get the promotion he so desperately wanted and Tony to fill a vacant position in the organization with a top earner.

4. Lending Artie Money

Another demonstration of why doing business with friends never really works out, here Tony’s childhood friend Artie Bucco (John Ventimiglia) needs to borrow $50,000 in the short term. The story is that he wants to invest in a new liqueur, but he really just wants to show off in front of his new hostess, Élodie (Murielle Arden). Artie goes to Ralph for the money first, but he tells him that he, “wouldn’t be able to hurt” him if his debt were to go into default.

Tony, meanwhile, after being particularly down on himself since learning about the suicide of his former girlfriend, Gloria (Annabella Sciorra), starts drunkenly reaching out to those around him for validation. When he learns of Artie’s meeting with Ralph, he stumbles to his doorstep, pulls a wad of money out, and hands it to Artie with the promise that the remainder will be dropped off later. It doesn’t take long before it becomes apparent that Artie has been taken for a ride, and after a disastrous attempt at trying to collect, he tries to kill himself with alcohol and sleeping pills.

While visiting him in the hospital, Tony sympathetically agrees to take on the debt and collect in exchange for having his $6,000 tab wiped clean. Unfortunately, Artie assumes that this was Tony’s plan all along, which infuriates Tony, who then takes Artie’s valuables and demands that he tell everyone a story about him getting robbed. While they eventually reconcile, the two would remain on the outs for almost a year.

3. Beating Ralph To Death

Tony’s temper had gotten the better of him around Ralph before, but for a while it seemed like the two of them had been able to bury the hatchet — just deep enough to stay in business together, if nothing else. Eventually, the two of them even invest in a racehorse together, Pie-O-My, which indirectly causes their considerable falling out.

After Ralph’s son is seriously injured while playing with a friend, Ralph orders the stable where Pie-O-My is kept to be burned down, which kills their horse, and several others, all so he can collect the insurance money. Tony, blinded with rage and either unwilling or unable to recall how vital Ralph is to his family (as well as their New York allies) beats him to death in his own kitchen. Tony’s able to keep his impulsive act of violence a secret between him and his nephew, Christopher (Michael Imperioli), but Ralph’s sudden absence draws a lot of suspicion from everyone, aggravates his relationship with New York, and prompts a lot of gossip behind his back.

2. Making His Uncle Boss (In Name Only)

Very early on, Jackie Aprile (Michael Rispoli), the acting boss of the family, was quickly headed toward his death bed due to cancer, necessitating the need for a new boss to be chosen. While Tony was considered the favorite, he defaulted to his Uncle Junior (Dominic Chianese), who was not only his respected elder, but someone who had eagerly longed for the “big chair” for many years. The decision allowed the two of them to avoid a violent and destructive war (for a time, at least).

The catch is that Tony, who had already become the family’s default leader while Jackie was cancer-stricken, made Junior the boss in name only. He did this for two reasons: one, to placate Junior, and two, to have him act as a lightning rod in the event of any federal investigations. It didn’t take long before cracks in the facade started to show, and after Junior’s arrest at the end of season one, the FBI used Tony’s power move against him to try and get under his skin. While it never comes up again directly, it’s something that eats away at Junior as he slowly starts to lose his mind during his years of house arrest.

1. Telling Off Johnny Sack

When Tony’s cousin, Tony Blundetto (Steve Buscemi), decides to hire himself out as a hired gun in the war between Johnny Sack (Vincent Curatola) and Carmine Lupertazzi Jr. (Ray Abruzzo), it exacerbates the growing rift between the Sopranos and the New York family. Demonstrating that he has some of his cousin’s bad temper, Tony B. goes rogue and kills New York mobster Billy Leotardo (Chris Caldovino), forcing him to go into hiding. Knowing his cousin’s fate is sealed, Tony pleads with Johnny Sack to give him a quick death, a request Johnny flat out refuses.

At this point, Johnny Sack had just won the aforementioned war with Carmine Jr., making him the boss of a New York family. His general tone of arrogance, such as his decision that their meeting places were now “undignified,” sets Tony off. Tony tells Johnny to “go f*ck yourself,” before reminding him that Tony B. was his cousin, and proceeds to handle the problem himself. It turned out that Johnny’s reign was brief, as he was arrested by the FBI only a couple of episodes later, but the bad blood between the two families only gets worse during the reign of Phil Leotardo (Frank Vincent), Billy’s older brother, who now has nothing but resentment for the entire Soprano family, which comes back to haunt Tony throughout the remainder of the show’s run.