Ranking The Least Trustworthy Characters On ‘The Sopranos’

Granted, while most of the characters on The Sopranos (available to stream anytime on HBO Now) are thieving, murderous criminals, stuffing envelopes with ill-gotten cash to pay tribute to their superiors, there was some sort of code they lived by. “Everyone involved… knows the stakes,” explained Tony Soprano (James Gandolfini) during one of his therapy sessions with Dr. Melfi (Lorraine Bracco), a now infamous excuse for the kind of reprehensible behavior that lined his pockets.

But for all those who lived by the mafia’s code of honor, there were a few who chose to ignore it at their convenience. They lied, cheated, and backstabbed their way through the ranks, making them little more than pariahs, even in the eyes of their fellow criminals. With that in mind, here’s a ranking at the show’s least trustworthy characters.

15. Carmela Soprano

A mostly devoted wife who was always capable of looking past her husband’s discrepancies, Carmela (Edie Falco) ended up accumulating a few of her own along the way. When she was having new wallpaper put up in her dining room, she came close to a romantic entanglement with the contractor, Vic Musto (Joe Penny). Years later, her and Furio (Federico Castelluccio) developed a similar flirtatious relationship. And during her separation from Tony, she has a full-blown affair with her son’s guidance counselor, Mr. Wegler (David Strathairn), though her trysts pale in comparison to her husband’s indiscretions during that time (or any other time, for that matter).

Eventually, when her and Tony reconciled, she does so on the condition that he builds her a spec house. She’d long fought for financial security in case of her husband’s death (including stealing $40,000 in cash from him), and realizing just how difficult it would to move forward as a divorced mob wife, she puts her true feelings aside in favor of a more stable future for her and her children.

14. Silvio Dante

A dedicated consigliere to Tony Soprano, not to mention a lifelong friend, Silvio (Stephen Van Zandt) did go behind Tony’s back when he okayed the theft of some fiber optic wiring from the esplanade construction site — after the site was deemed to be a theft-free zone. When asked about it by his boss, Silvio simply shrugged it off, saying simply that the “timeline got f*cked up.” While Tony ended up letting the whole thing go, and it failed to have a major impact on their relationship, it served as an uncomfortable reminder that everyone in Tony’s life had ulterior motives.

13. Christopher Moltisanti

His entire life, Christopher wanted nothing more than to be a feared, respected member of the Soprano family. When he applied himself, he’d move up the ladder quickly, and at one point was even poised to become the acting boss of the family. But two things kept proving to be constant distractions: his desire to be a Hollywood big-shot, and his recurring drug addiction. While his Tinseltown aspirations proved to be problematic, it was his addiction that ended up being his undoing, reducing him in Tony’s eyes to nothing more than a junkie who’d eventually flip over “a nickel bag of white powder,” a risk that Tony eventually realized he couldn’t afford to take.

12. Raymond Curto

A seemingly loyal captain in the Soprano family, Raymond Curto (George Loros) was mostly a background character — despite being Tony’s choice for ‘the big chair’ way back in season one. When Raymond was around, though, it turned out he was recording everything for the FBI. Granted, whatever he got on tape never seemed to amount to much, as it never seemed to move the criminal investigation against the family any further.

Then, without warning, he died of a stroke in Agent Sansaverino’s (Karen Young) car, and was laid to rest being regarded as a good, honorable man — the kind Tony wasn’t able to find anymore. Though he’s not the first person in Tony’s life (or on this list) to talk to the FBI, Raymond’s distance from Tony, and his general lack of screentime, made his betrayal seem pale by comparison.

11. Jackie Aprile, Jr.

After initially being shown the ropes of the business by his uncle Richie (David Proval), Tony ended up taking a special interest in Jackie Jr. (Jason Cerbone). Despite his aspirations of becoming a big, important mafioso like his father, the late Jackie Sr. (Michael Rispoli), Tony tried to steer him away from all that, making sure he stayed in school, got good grades, and most importantly, didn’t follow in his family’s footsteps. When he started dating Tony’s daughter, Meadow (Jamie Lynn-Sigler), Tony’s went out of his way to try and make sure Jackie Jr. did the right thing.

But all the fatherly guidance, scrutiny, and tough love didn’t prevent Jackie Jr. from being a perpetual disappointment. He not only ignored pretty much everything he’d been told by Tony and went ahead with a badly botched card game robbery, but he also repeatedly betrayed Meadow’s trust, burning every possible bridge with the Soprano family before he got taken out.

10. Paulie Gualtieri

For a long-serving member of the Soprano family, going back to the days of Tony’s father, Johnny Boy (Joseph Siravo), Paulie (Tony Sirico) sure made some dubious decisions over the years. Including unnecessarily provoking a Russian mob associate during a routine pickup, then trying to lie his way out of it once the whole fiasco got him and Christopher (Michael Imperioli) lost in the woods. Later, during a stint behind bars, he freely gave up Soprano family secrets to New York underboss Johnny Sack (Vincent Curatola), which not only threw the family into disarray, but it caused some serious doubt as to where Paulie’s heart was.

Finally, when Tony was in a coma with a gunshot wound, he began to wonder why he should even be paying tribute to Carmela (Edie Falco), believing all that money would be wasted if Tony ended up not pulling through. Despite all his actions, however, Paulie would do everything he could to slink his way back into Tony’s good graces with fat envelopes and fancy coffee machines, always desperate to prove his (tentative) loyalty to his boss.

9. Ralph Ciferetto

It says a lot about a guy when even his fellow criminals didn’t have anything nice to say about him. Generally sleazy, undermining, and only out for himself, Ralph (Joe Pantoliano) cemented his despicable legacy after brutally murdering Tracee (Ariel Kiley), a Bada Bing dancer behind the club after she revealed she was pregnant with his child. Still, while Tony wanted nothing more than to be rid of Ralph permanently, he brought in far too much cash to do so. It wasn’t until Ralph killed their racehorse for the insurance money, (and brazenly denied it until the very last moment), that Tony finally hit his breaking point with him.

8. Junior Soprano

Once a sharp and cunning gangster, Tony couldn’t bring himself to actually cede the position of boss to his uncle Junior (Dominic Chianese), and instead gave him the title without any of the responsibility. When he got wise to this, Junior conspired with Tony’s mother, Livia (Nancy Marchand) to take Tony out — and very nearly succeeded. While Junior readily admitted to his role, he never stopped covering up Livia’s involvement. Though he tried to become a counselor to Tony after all this had blown over, a life confined to house arrest got the best of him, and he ended up spending the rest of his life inside a state-run mental facility with only a vague recollection of who he once was.

7. Tony Blundetto

Despite his intentions to go straight after a 20-year stint in the can, Tony Soprano’s cousin, Tony Blundetto (Steve Buscemi) soon found himself back to his old life. Amidst a power struggle between rival factions of a New York family, Tony Soprano urged his family to do everything they could to stay out of it. But the lure of money, and the chance to provide a better life for his twins was too much for Tony B., and he put himself smack dab in the middle of the conflict. To make matters worse, he lied about it to his cousin, putting the entire Soprano crew in grave danger. Even though he eventually came clean about his role, it permanently strained Tony’s relationship with New York, and started to cost him the trust of those closest to him.

6. Richie Aprile

Believing he was owed something after his time spent behind bars, Richie (David Proval) came back to North Jersey with a chip on his shoulder and vengeance on his mind. After taking out his rage on an undeserving Beansie Gaeta (Paul Herman) against Tony’s specific order not to, Richie decided he was unhappy with the current state of Soprano leadership. After deciding to move against Tony, Richie soon discovered that he didn’t have the support he’d expected. Even Junior went along with the idea to try and hedge his bets, and ultimately sided with his nephew. Frustrated, undermined, and defeated, Richie went to the grave (or, in this case, the meat grinder) without anyone willing to mourn his loss.

5. ‘Big Pussy’ Bompensiero

Out of all the betrayals that Tony Soprano has dealt with over the years, the betrayal of his best friend, Sal “Big Pussy” Bompensiero (Vincent Pastore), hit him the hardest. As an FBI informant, Pussy tried to tow the line for a while, feeding them “disinformation” to buy him some time, but he eventually grew tired of being passed over for promotion and tried to be as much of an asset to the Feds as he could. The FBI mostly balked at his attempts to become a junior G-man, and Tony had to confront a fact he’d been wrestling with for years: that Pussy had betrayed the family and only he could put a stop to it.

4. Butch DeConcini

While he didn’t show up until the show’s last season, Butch (Greg Antonacci) proved to be a master manipulator. While Tony and his crew had targets on their backs thanks to Phil Leotardo (Frank Vincent), Butch started to second-guess his boss’s decision, and agreed to sit down with Tony to try to come up with the best possible resolution — which was to take Phil out of the picture altogether. However, Butch refused to give up Phil’s location, and made Tony’s guys do all the work finding him. Once Phil was gone, Butch became the de facto boss of the New York family, and (depending on your interpretation of the show’s final moments), kept Phil’s plan in motion to do away with Tony permanently, which further consolidated his newfound power.

3. Janice Soprano

When Tony’s sister, Janice (Aida Turturro), drifted into New Jersey, she was feigning concern for her ailing mother, but really just wanted to acquire her house so she could scour the place for a stockpile of cash she believed was stashed in the walls. She also carried on affairs with those that conspired against her brother, often cheering on their plans. Though she eventually married the endearingly loyal Bobby Bacala (Steve Schirripa), it was a relationship she conspired her way into thanks to a well-placed ouija board and a fake AIM account. In the end, she made a last-ditch effort to pry her uncle Junior for whatever money he might have had left. Though Junior was a shell of his former self by then, he managed to recall Janice being deceptive, underhanded little girl, which spoke volumes about the kind of person she really was.

2. Tony Soprano

Of course, you can’t talk about distrust in the Soprano family without mentioning the patriarch himself. From his numerous, wanton sexual affairs, his constant disregard for telling the truth (even to his therapist), to the fact that he always placed utmost importance on his own selfish, emotional needs while disregarding everyone else’s, Tony simply was not a guy who could be trusted. Sure, he might have tried to appear to do the right thing, providing a life for his wife and children, and he often appeared to be a strong, capable leader for his crime family, but time and again, Tony proved himself a petty, shortsighted, ultimately immature man whose own self-interest won out every time.

1. Livia Soprano

It’s no coincidence that the person who’d have the greatest impact on Tony’s life would also be the least trustworthy. Despite her son’s genuine love and affection toward her, Livia always conspired against him while she hid behind her guise of being a frail old woman who didn’t know any better. Even though Tony eventually wised up to the ordeal (albeit a little late), Livia’s legacy will always be remembered as shrewd, deceptive, and ultimately irredeemable person who didn’t seem to care for anyone.