Tony Soprano is perhaps the greatest antihero in television history. He’s the head of his own household, as well as the boss of the Soprano crime family. His numerous and severe character flaws make both of these roles increasingly difficult for him over the course of the series.
The New York bosses question his abilities as a boss, referring to the Soprano family as a “glorified crew” under Tony’s leadership. Throughout The Sopranos, Tony does make several questionable decisions, but also some good ones. It should be noted that often the “good business decisions” involve morally indefensible acts. Though these acts aren’t condoned, they fit within his role as a crime boss.
Best: Never Admitting The Truth About Ralph’s Disappearance
In the mixed series finale, Paulie Walnuts refers to Ralph Cifaretto as “Ralphie MIA.” This is because Tony never admitted to killing Ralph with his bare hands after accusing him of killing his racehorse, Pie O My. Several of Tony’s associates suspected Tony had killed him, but Tony’s decision never to admit it was undoubtedly the right one.
As despicable as Ralph was, he was a made man, which afforded him certain protections. Had it ever become known for sure that Tony killed him over the death of a horse, it would have greatly undermined his underlings’ trust.
Worst: Protecting Tony Blundetto From The New York Bosses
Tony obviously had a soft spot for his cousin, Tony Blundetto, played by the great Steve Buscemi in Season Five. Blundetto whacks Billy Leotardo, brother of Phil Leotardo, the New York boss. Phil is devastated and infuriated, insisting that Tony Soprano allow him to exact his revenge on Tony B.
Tony refuses to give his cousin up, which is a large part of what escalates tensions between the Jersey and New York families into an all-out war in Season Six. Tony’s associates also feel as though they’re being unfairly endangered by Tony’s emotional decision to protect his cousin, and they’re not wrong.
Best: Letting Silvio Whack Adriana
When Adriana confesses to Christopher that she has been cooperating with the FBI, he is predictably devastated. He knows what has to be done, but he doesn’t have it in him to do it. The scene is shown in a flashback, where he approaches Tony with the news. Normally, the boss would make Christopher clean up his own mess, but Tony knows his nephew all too well and realizes that it’s beyond him to carry out the hit.
Instead, he enlists his most trusted consigliere, Silvio, to do the deed. The scene in which Silvio kills Adriana is one of the most disturbing in the entire series, but from a strictly business perspective, Tony made the right decision by letting Sil handle it.
Worst: Personally Carrying Out The Matt Bevilaqua Hit
Matt Bevilaqua and Sean Gismonte try and whack Christopher in order to curry favor with Richie Aprile. Sean dies on the job, but Matt runs away.
Big Pussy gets tipped off to Bevilaqua’s whereabouts and goes to kill him. Tony insists on coming along, despite Pussy’s assurances that he can handle it himself. Tony wants to join because the hit is personal to him, but this ends up causing far more trouble than it was worth, as Tony was spotted by a witness that night. This would have led to his being indicted for murder if Paulie and the crew didn’t “convince” the witness to forget what he saw.
Best: Giving Junior The Throne
Early in the series, when boss Jackie Aprile dies of cancer, Uncle Junior has his eyes on the top spot within the Jersey family. This creates tension between Tony and Junior, but ultimately, Tony makes the wise decision to give Junior the satisfaction of being officially crowned the “boss,” even though everyone but Junior himself understands that Tony is the one actually calling the shots.
Not only does this arrangement help keep the peace between Junior and Tony, but it also keeps Junior’s face atop the pile on the FBI’s bulletin board instead of Tony’s, as the authorities also recognize Junior as the boss.
Worst: Letting Bobby Baccalieri, Sr. Whack Mustang Sally
Mustang Sally is a street thug who viciously beats Vito’s brother with a golf club in broad daylight, putting him in a coma. Tony sends Bobby Baccalieri, Sr. to kill him in retaliation. Bobby is a sick old man who’s dying of lung cancer and is clearly incapable of doing the job without making a huge mess of it.
Bobby nearly botches the job altogether, as the hit goes horribly wrong. He does kill Mustang Sally in the end, but the struggle triggers a respiratory episode in which Baccalieri starts coughing up blood in his car. He loses control of the vehicle, crashes into a telephone pole, and dies. This was a foreseeable outcome, making Tony’s decision to assign him the job inexplicably stupid.
Best: Not Whacking Paulie Walnuts
One of the series’ tensest moments takes place when Tony considers whacking Paulie on a boat. He had rightly questioned Paulie’s loyalty over the years and had become increasingly concerned with Paulie’s tendency to run his mouth, even to complete strangers.
Ultimately, he decides against it, largely owing to the advice of his friend Beansie, who reminds Tony that Paulie loves him and loves the gangster life. In the end, Paulie is one of the only members of the Soprano crew who survives the war with New York, and Tony promotes him in the series finale. As it turns out, Tony couldn’t afford to lose Paulie, and so his decision to spare him paid off.
Worst: Making Bobby Bacala Kill
Bobby Baccalieri Jr., aka Bobby “Bacala,” is the ultra-rare example of a made man who has never killed before. In the final season’s “Soprano Home Movies” episode, Tony and Bobby get into a physical fight in which Tony loses, leaving Tony feeling emasculated.
Later on, when he’s approached with a job offer involving a hit on a total stranger, Tony makes Bobby do the deed. This is clearly a petty and evil decision based purely on spite and Tony’s own insecurities.
Best: Calling Off The Hit On Carmine
Tony and Johnny Sack make a pact to take out New York boss Carmine Lupertazzi, Sr. Tony eventually calls it off, much to Johnny’s disappointment. Ultimately, Tony made the right call, seeing as the dispute had been settled, and Johnny Sack wasn’t in a position to retaliate against Tony for backing out.
Johnny may have said his vendetta against Carmine was for professional reasons, but everyone knew that he had personal reasons too. So once business matters were settled, it didn’t make sense for Tony to go through with the hit.
Worst: Not Letting New York Kill Ralph
When Ralph Cifaretto cracks a rude joke about Johnny Sack’s wife at a dinner party, Johnny wants to avenge her by having Ralph whacked. Tony doesn’t agree to it and defends Ralph.
Under normal circumstances, this would be the right decision, but being that Ralph was so reviled by almost everyone in each of the families, Tony should have seized this opportunity to be rid of him, as letting New York handle it would have rid Tony of Ralph without having to take responsibility for his death.