As boss of the DiMeo crime family, Tony Soprano took good care of himself and he made his way through the show’s six seasons without ever getting imprisoned or whacked on-screen. But whether Tony took good care of his organized crime unit as a whole or not is a matter that’s up for debate, as there were far too many problems that stained his tenure.
It was during Tony’s reign that the New Jersey and New York crews engaged in a cold war before opting to slaughter each other. It was also during Tony’s reign that several members of the family ended up becoming FBI informants. Given how often things went wrong, it’s likely that the situation would have been different with someone else at the helm.
Bobby spent the early part of the series being Corrado “Junior” Soprano’s right-hand man and the target of all jokes because he was too nice. He saw his fortunes rise when he married Tony’s sister, Janice. By the time the show was coming to a close, he had risen to the rank of Underboss.
Bobby would have made a different kind of boss because he was anti-violence. Throughout his entire career as a mobster, he only killed one person. He didn’t even “make his bones.” His rule would have been characterized by cordial relationships and less bloodshed, two things that Tony struggled with.
Ralph was a character fans loved to hate. He gladly spun of out-of-control on a regular basis and no one was bold enough to stop him. The terrifying capo enjoyed feuding with his colleagues and harming people for no good reason. Thanks to his unpredictability, he gained notoriety for being a mobster not to be messed with.
Business acumen is what made Ralph a perfect candidate for boss. As intemperate as he was, he was the highest-earning capo in the family. Revenue is important to organized crime players and Ralph could have ensured the accounts were always healthy, guaranteeing long-term stability.
Tony could be unbelievably reckless in his decision-making sometimes. Luckily, he had the Consigliere Silvio Dante by his side, who always made sure to remind him not to be stupid. Silvio also built a reputation for himself as the “snitch eliminator,” as he participated in almost every whacking of FBI informants.
The great pieces of advice that Silvio offered Tony hinted at him becoming a wise boss if he ascended to that level. No actions would be taken that would be detrimental to the family. He also dressed the part and stood out as the most fashionable member of the DiMeo Crime Family. Most importantly, Silvio had a serious face at all times. Bosses need to be tough to earn respect and Silvio would have had no problem with that.
Furio started out as a member of Annalisa Zucca’s crew, but Tony developed a liking for him during his visit to Italy, so he brought him to America. In New Jersey, Furio became Tony’s most trusted enforcer.
Since he hailed from Naples, Furio was a member of the original Cosa Nostra. As boss, he’d have strong mob ties not just in America but in Italy as well. His no-nonsense attitude would have translated to him getting total respect from his peers and subordinates. Furio valued loyalty to wives, which could have guaranteed him a peaceful home life, unlike Tony, and would have enabled him to fully focus on his work.
A central member of Tony’s crew, Paulie is as colorful of a character as he is ruthless. No one else whacked more people than him. He was also the only member of Tony’s inner circle to finish the series without being physically harmed or chilled.
One of the reasons Paulie qualifies to be boss was because he has way more experience than anyone else (he became a “made guy” in the ’70s). His cautious ways and ability to avoid physical harm would have served him well if he were to take up the top job. It was an open secret that the Don was never safe. Even Tony, allegedly, got the Michael Corleone treatment in the final minutes.
Vito’s hard work and earning ability hastily catapulted him from street soldier to capo. Ambition is a valuable trait in organized crime and he knew that very well. When Tony’s future became uncertain after the shooting incident in season 6, he rallied his colleagues to support him in case a vacancy for Don opened up.
As a member of the LGBTQ+ community, Vito would most likely have pushed for a change in mafioso rules to allow tolerance and acceptance. That’s something Tony sat on the fence about, allowing the discrimination to continue. Tony had moments of near-bankruptcy, but Vito’s prowess at bringing in the bucks would also have ensured financial solidity and liquidity in the DiMeo Crime Family.
Like Bobby, Patsy was not a violent man and he was never seen killing a single man on the show. However, the accountant’s intimidation skills were legendary. Apart from serving as the DiMeo family’s accountant, he was occasionally tasked with intimidating people in situations where murder wouldn’t have been necessary.
An alternate world with Patsy as boss would have been characterized by less carnage and total respect and murder would only be a last resort. There would also be no cases of capos and street soldiers withholding funds, like what Paulie did when Tony when hospitalized. Patsy’s experience as an accountant would have enabled him to account for every coin and weed out non-performers with ease.
The youngest mobster in The Sopranos showed a lot of promise. Tony even declared that Christopher was the future of the family. Even though that didn’t happen, the family would have been better if it did.
Christopher had a vision that extended beyond organized crime. He didn’t believe in mobsters only doing illegal things. That’s why he was able to turn his dream of making a movie into reality. Unlike Tony, who believed in using the old mafioso money-making schemes like racketeering and gambling, Christopher would have set up a few legal businesses that could have kept the feds away.
Gianluigi ”Gigi” Cestone
Gigi was the only person in the DiMeo Crime Family to serve three different crews. He moved from Tony’s crew (when Tony was still a capo) to Junior’s crew, before eventually becoming capo of the Aprille Crew.
There was a reason why Gigi’s services are sought after by many. He executes tasks efficiently, noticeable in how he flawlessly shoots Phil Parisi inside a vehicle. A hardworking mobster like him would have an easy time as boss. Gigi was also quick to spot changing tides and that’s why he jumped from Junior’s crew back to Tony’s. This was a trait he shared with Tony, meaning what Tony had been able to do, Gigi could too.
Richie was arguably the scariest mobster in The Sopranos. He spent several years behind bars before being released and returning to New Jersey to terrorize everyone.
The ruthless mobster had a supportive partner in Janice, who wanted him to become boss, and that would have meant him having all the moral support he needed if he ever reached that level. Tony lacked moral support from Carmela. Richie’s reputation of brutalizing foes (seen from how he handled Beansie Gaeta) would have barred people from messing with him, compared to Tony, who had no respect from people like Phil Leotardo.