The Sopranos’ characters were always in trouble, and part of that can be attributed to some of the worst, ill-advised decisions some of them made.
Part of The Sopranos’ appeal is how well-developed the characters are, but even the best characters can make some of the worst decisions that have dire consequences on the show as a whole. Some of these decisions only look worse in hindsight, and some of these dumb decisions reflect how human The Sopranos’ characters are. Nonetheless, these decisions factored into the story, with some of them having long-lasting consequences in what is widely recognized as one of the best TV shows of all time.
Of course, some characters always make dim-witted decisions, like AJ Soprano. The difference is that AJ’s lack of foresight doesn’t impact The Sopranos storyline and reflects more on his shortcomings. Another example is Christopher Moltisanti, whose bad choices sometimes factor into the story, but it hits hardest when they play a role in his death in season 6. These decisions had ramifications for the entire series that could have prevented a lot of trouble had they gone the other way.
8. Paulie Causing Unnecessary Trouble With Valery
Season 3, Episode 11, “Pine Barrens”
“Pine Barrens” is among the best episodes of The Sopranos because of its humor, ambiguity, and how it looks at some of the character dynamics. However, in what should have been a routine collection that should not have presented any trouble, an annoyed Paulie antagonizes Valery, leading to a chain reaction that ends in Paulie and Christopher being stuck in freezing cold in the woods. Paulie’s decision to make a situation difficult when he didn’t have to begin the strain between him and Christopher and between him and Tony.
7. Matthew Bevilaqua & Sean Gismonte Try To Take Out Christopher
Season 2, Episode 8, “Full Leather Jacket”
After being fed up with the mob’s constant abuse, Matthew Bevilaqua and Sean Gismonte think killing their friend Christopher will score points with Richie Aprile, which would help their quest to move up. Not only do they fail, as Moltisanti kills Gismonte, but Aprile rebukes Bevilaqua for trying to pull off that stunt. Eventually, Bevilaqua, too, would be killed off. Their actions effectively ended both of their lives when they should have realized that crossing the mafia in the hopes of moving up would come with dire consequences.
6. Jackie Jr. ‘Robs’ Ralph Cifaretto’s Card Game
Season 3, Episode 12, “Amour Fou”
After hearing about how his father, Jackie Aprile, worked his way up in the mob, Jackie Jr. thought he could do the same in the same fashion. Jackie gathers his friends, Dino and Carlo, to rob Ralph’s card game to become “made” gangsters. However, because the boys are amateurs hopped up on drugs, the robbery goes awry, leading to almost everyone getting killed. Jackie may have had a chance in the mafia had he been patient, but because he wanted the easy way out, he got himself killed. Acting dumb was nothing new to Jackie, but crossing the mob signed his death warrant
5. Vito Spatafore Returns To New Jersey After Being Outed
Season 6, Episode 11, “Cold Stones”
After deciding that he missed life in the mafia and with his family, Vito returns to New Jersey, hoping to return to Tony’s good graces. However, Vito had previously been outed as gay. Despite Vito being a good earner for the business, it didn’t take long for him to face undeserved repercussions, as Phil Leotardo quickly has him killed. Even worse, Tony would have done the same had he gotten to Vito first. Had he just stayed out in his new life in New Hampshire and never returned to the family, Vito likely would have been unscathed.
4. Tony Takes Too Long To Kill Pussy
Season 2, Episode 13, “Funhouse”
Tony found out early on in season 1 that one of his closest friends, Sal “Big Pussy” Bonpensero, is an FBI informant. Tony refuses to believe it initially but confirms it in one of The Sopranos’ greatest betrayals. Tony putting it off led to Pussy giving the feds who know how much information. The worst part in all of this is that Tony had been informed months back about what was really going on, and after killing his friend, he came to realize that it must have been happening for years. This likely played a factor in how the feds built a case against the mafioso.
3. Tony Blundetto Killing Joey Peeps
Season 5, Episode 8, “Marco Polo”
Tony Blundetto ranks among the more tragic characters in The Sopranos, as it really felt as though he was going on the straight and narrow until he felt the need to get back into the game. Peeps was not the first person he killed, but it led to retaliation from both New York and New Jersey, which ended with Blundetto killing Billy Leotardo. While this led to Tony Soprano killing his own cousin in one of The Sopranos’ saddest deaths, it did irreparable damage to New York and New Jersey’s relationship. Had Tony B continued on the straight and narrow, there may have never been a war.
2. Christopher Choosing Tony Over Adriana
Season 5, Episode 12, “Long Term Parking”
After Adriana confesses to Christopher that she’s been forced to be an FBI informant, Christopher initially decides to accompany her as they enter the Witness Protection Program. However, at the last second, he changes his mind and rats her out to Tony, leading to her death. While ratting out his own fiance was hard enough, choosing Tony led to Christopher’s relapse into his alcohol and drug addiction, which ultimately led to his death. All of that would have likely been avoided had he chosen to be with Adriana, who genuinely loved Christopher and would never have hurt him.
1. Tony Nearly Killing Coco
Season 6, Episode 19, “The Second Coming”
After New York’s Coco Gogliano sexually harasses Tony’s daughter, Meadow, Tony gives him a well-deserved beatdown, but he does it without any permission from the New York crime family. Since tensions were already high between New Jersey and New York, Tony’s decisions led to a war that resulted in a few of his men dying and potentially Tony’s death as well. Tony going for revenge was inevitable, but considering how the war was already about to start, he should have been much smarter with his actions. Regardless, this was a major turning point for The Sopranos and might have sealed Tony’s fate.
