A show like The Sopranos, (available to stream anytime on HBO Now), set in the violent world of the mafia, is bound to have more than its share of tragedy. The world of mob boss Tony Soprano (James Gandolfini) is based on usury, manipulation, intimidation, and murder, and anyone who got caught up in this world was bound to be chewed up and spit out like gum that’s lost all its flavor. Some of those who ended up discarded were lucky to walk away with nothing, where others weren’t able to walk away at all. Here are the 10 most tragic characters in Sopranos history.
10) ‘Pussy’ Bompensiero
Thanks to some well-timed food poisoning and a night of fever dreams, Tony realized what needed to be done after spending the better part of a year wrestling with the possibility that his associate and best friend, Sal ‘Big Pussy’ Bompensiero (Vincent Pastore), was talking to the FBI. Tony, Silvio, and Paulie (Tony Sirico) lured Bompensiero onto a boat in the middle of an ocean and, after a round of tequila shots, killed him. Knowing what was in store, Pussy even broke down and begged for forgiveness, going on and on about how he used disinformation in a desperate, last-ditch attempt to keep himself alive. It wasn’t enough, and in the end, they didn’t even let him sit down.
9) Junior Soprano
It’s easy to write off the human side of a character like Corrado ‘Junior’ Soprano. He was manipulated by Tony’s own mother, Livia (Nancy Marchand), into killing her son, and after a brief reign as boss, he ended up behind bars by the end of the first season. Later, he was placed under house arrest, and spent the rest of the show slowly withering away inside his wood-paneled walls.
Even after (sort-of) making amends with Tony, his mind gradually decayed to the point where he tried to kill him a second time, and spent his few remaining days in a run-down state mental hospital devoid of any real idea of who he was. He might not have been the most likable guy, but his life ending like that is enough to make even Tony shed a tear.
8) Vin Makazian
A police detective who had a side job as Tony’s personal private investigator, Vin Makazian provided valuable information that afforded him some leeway with his gambling issues. He never could quite get his life in order, but he was nonetheless a valuable commodity to Tony, even though Tony showed it by mercilessly berating him, calling him a “degenerate gambler with a badge,” only to turn around and placate him when he’d gone a little too far.
When he was busted in a prostitution raid with a few members of Tony’s crew, Vin couldn’t bring himself to add “disgraced cop” to his resume, and he decided to end it all. His death may have had little impact on Tony, though the information that died with him proved to be devastating, which didn’t help Tony’s slide into a deep depression.
7) Vito Spatafore Jr.
After his father’s public outing, prolonged absence, and then brutal murder, Vito Spatafore Jr. (Brandon Hannan) ended up harboring quite a few issues — and understandably so. He fancied himself a goth kid, wore black-and-white makeup, and, when bullied by classmates, he retaliated in very extreme ways. Both his uncle, Phil Leotardo (Frank Vincent), and Tony even tried to have heart-to-heart talks in an attempt to help. Seeing no other option, his mother, Marie (Elizabeth Bracco), begged Tony for enough money so she and her kids could simply move away, giving them all a chance to start over far from the shadow that the mob cast over their lives.
Had Marie asked Tony on a different day, things might have worked out that way, instead, she caught Tony amidst a particularly bad losing streak, and he offered up a cheaper alternative: send Vito Jr. to a child boot camp. Not seeing any other option, Marie agreed, and in the middle of the night, two men came into their home and dragged her son screaming into their van before driving off. Pretty rough ending for a once-normal kid whose life ends up ruined by circumstance.
6) Davey Scatino
Davey Scatino (Robert Patrick) was a small-time gambler who probably spent a little too much time at Richie Aprile’s (David Proval) card games, but it was when he tried to leverage his longtime friendship with Tony that he not only ruined his life but his family’s lives too. And after running up a $50,000 debt to his former friend, Davey learned very quickly that his years of history with Tony meant very little.
To recoup the money he owed them, Tony and company descended on Davey’s sporting goods store, running up his credit for bulk orders of everything from barber scissors to airline tickets to sell on the black market. As a result, Davey’s personal life fell apart, he alienated himself from his wife and son, contemplated suicide, and after he was left with nothing, left New Jersey in hopes of starting over out west. While his world was crashing down around him, it was just another run-of-the-mill business transaction for Tony and his crew.