Deaths That Affected Tony Soprano The Most

A lot of people die on "The Sopranos." Most of those deaths affect Tony Soprano in one way or another. Some were even perpetrated by Tony himself. Either way, the bodies stack up and stick with Tony — by the end he has moments where you can see everything he's done and will have to do physically dragging him down. While the show did a lot for the actors who appeared in it, the role of Tony Soprano supposedly wore on the actor who played him, the late James Gandolfini. It will be amazing to see a young, unburdened Tony Soprano (played by Gandolfini's son Michael, no less) in "The Many Saints of Newark," his soul untarnished by so many deaths and murders. Especially since some of those who die will be right alongside him as young up-and-comers.

Organized crime is a bloody business. Very few people in the game are afforded the luxury of dying of natural causes at an old age (except, ironically, several of the biggest bosses in "The Sopranos"), and the deaths in Tony's life follow suit. Quite a few times Tony has to kill the people who are closest to him for the sake of the family, though at great personal cost. There are also times when he has to kill people close to him and it's a relief. Some deaths on "The Sopranos" are good for the man, some are bad, but most are a little of both. It's almost as if Tony Soprano rises to the top on a pile of bodies. Here are the ones that affected him the most.

The death of Jackie Aprile (Michael Rispoli) sets up "The Sopranos." When the show starts, Tony Soprano is an underboss working loyally for his longtime friend, Jackie Aprile, head of the DiMeo crime family. Tony's respect and love for his longtime friend is undeniable, and we'll probably get a glimpse of where that loyalty began when they both appear as kids in "The Many Saints of Newark."

As Jackie's dying from cancer, Tony starts taking over more responsibility but still pays Jackie respect, visiting him in the hospital, even bringing a girl from his strip club. Jackie Aprile's death hits Tony hard. It also leaves a big power vacuum in the DiMeo family. Jackie doesn't want his son, Jackie Jr., to be in the life. Tony's already the de facto leader but his uncle, Corrado Jr., aka Uncle Junior (Dominic Chianese), thinks it's his time to be the boss. Tony lets Junior act as the head but is really pulling the strings. When Corrado finds out, it leads to some bad blood. Tony eventually wins out, but it's a tough battle that even sees him survive a hit orchestrated by his own uncle.

So Jackie's death results in Tony losing one of his oldest friends, fighting his uncle, and eventually to Tony becoming the boss of North Jersey.

Vin Makazian (John Heard) is Tony's pet Newark cop. Because of his gambling problem, Vin is in Tony's pocket and Tony lets him slide on some debts in exchange for the cop passing him insider info and sometimes running errands. Soprano is trying to steer the DiMeo family through a tough time with the illness of boss Jackie Aprile and his eventual takeover, so he can use all the help he can get. Vin is one of the first people to tell Tony he's heard Big Pussy (Vincent Pastore) is a Fed informant. That's the kind of info Tony really needs, but he disregards it because Vin owes Big Pussy $30,000.

Makazian is a degenerate in every way, even falling in love with a madam of a brothel. When the police raid her brothel and find him there, Makazian realizes he's ruined his life and there's no way out so he pulls over on a bridge, uses his badge to get through the traffic, and jumps off the edge to his death just when Tony could really use a friend with a badge. It also makes Tony realize that he treated the man poorly, bringing him back to his own battle with depression which, of course, is a driving storyline in a show about a mob boss going to therapy.

Richie Aprile (David Proval) is Jackie Aprile's older brother. In fact, he was brought into the DiMeo crime family before Tony, with a leather jacket he got by beating up the bigger Rocco DiMeo when he was making his bones. Richie eventually went to jail, getting released into a very different world. His younger brother is dead and this kid who was friends with Jackie, Tony Soprano, is now his boss.

Richie starts dating Tony's sister Janice (Aida Turturro) and the two soon move in together. While Richie is a thorn in Tony's side, the boss has to entertain the man at his dinner table thanks to Janice. Richie starts a campaign to take out Tony, even tries to get Junior in on it, but the old man chooses Tony. Richie's irascible and out for blood, and Tony knows he needs to get rid of the man. Just as he's getting ready to do so, Richie punches Janice at their home. She responds by silently going into another room, getting a gun, and shooting him dead.

The death of Richie is basically the end of all internal attempts to overthrow Tony, and places Aprile soldiers like the big-earning Vito Spatafore directly under Tony. A huge win.

This may be the death that hurts Tony the most. He dwells on it for the rest of the series. Tony heard whispers about Big Pussy betraying him to the Feds for a while, first brought up by Vin Makazian. It was tough for Tony to believe, though. He'd come up with Big Pussy, to the point where a younger version of Bonpensiero is in "The Many Saints of Newark." He's part of Tony's sacred inner circle, shoulder to shoulder with capo Paulie Gualtieri (Tony Sirico) and consigliere Silvio Dante (Steven Van Zandt). But the punishment for turning informant on the family is death, no matter who you are.

Tony, Silvio and Paulie take Pussy out to sea in a boat under the pretenses of buying the boat. There Tony has to confront his longtime friend and confidante before he, Paulie and Silvio shoot Pussy to death and bury him at sea.

The three of them are forever haunted by this betrayal and by having to kill one of their own. This also leads to the promotion of Tony's nephew Christopher Moltisanti, son of legend Dickie Moltisanti, bringing a whole slew of new headaches to poor Tony Soprano.

Tony's mom Livia (Nancy Marchand) is perhaps the most toxic person in his life, a tall order for a mob boss. Dr. Melfi (Lorraine Bracco) diagnoses Livia as having borderline personality disorder, and she and Tony constantly discuss how his never-happy, always-scheming, filicidal mom has screwed up his relationships with women and himself. It'll be interesting to see a younger version of her in "The Many Saints of Newark."

Livia's last big act before resigning herself to nitpicking at her son and daughter-in-law is being the birdie whispering in Junior's ear that he needs to whack his nephew. Even when Tony tries to do something nice for her the woman throws it back in his face. Her death from a stroke (necessary since Marchand died during filming) comes as a relief for Tony and his family.

Yet it also means that he has to deal with her estate, and with his broke, unmotivated sister Janice constantly trying to get more money from the estate. All told, it's still a good thing for the man.

Tony is connected romantically to three categories of women: his wife, Carmela; his goomars, or longterm mistresses; and the women he sleeps with on a whim. One of Tony's goomars is Gloria Trillo (Annabella Sciorra), a Mercedes saleswoman he meets at Dr. Melfi's waiting room.

Tony finds her exciting and strong, a woman who can support herself, unlike the other "gold diggers" he's taken on the side. Then she starts to exhibit her mental issues, going from rage to depression and then back. Eventually Tony sees a lot of his own mom in her, especially the woman's borderline personality disorder, and breaks it off. She begs for his help, then starts stalking him, even trying to become friends with his wife Carmela (Edie Falco). He sends Patsy Parisi (Dan Grimaldi) to threaten to kill her if she ever tries to contact the Sopranos again.

Next time she's mentioned, Tony hears from Carmela that her friend from the Mercedes dealership killed herself. Gloria's death haunts him, with her continually appearing in his dreams. As always, there's a mixture of regret over how he handled it and a worry about his own depression.

Tony Soprano loves animals, probably more than people. He goes through serious distress when a family of ducks that had been living in his pool leave. But no animal gets closer to Tony's heart than his horse, Pie-O-My, even if the horse had really been Ralph Cifaretto's (Joe Pantoliano). Ralph's a good earner, and a decent enough boyfriend to Jackie Aprile's widow.

Yet Ralph's also erratic and violent, harboring resentment that he's not even a capo while his old friend's a boss, and quick to make rude comments or, for example, beat to death the 21-year-old stripper who's pregnant with his kid. One comment about New York underboss Johnny Sack's wife leads Sack to ask for a hit on Ralph. 

Pie-O-My becomes a big earner for Tony and Ralph after Tony gives Ralph some racing tips and in turn Ralph gives him partial ownership. Tony falls in love with the horse but Ralph only sees it as a way of making money. He gets in a pinch and Pie-O-My's stable is burned down, fatally injuring the horse. Tony accuses Ralph of killing the horse for insurance money, and Ralph all but admits it, leading to a fight in which Tony kills the man with his own hands.

Not only does he lose a good earner, it also creates mistrust, with the crew wondering about a boss who kills a higher-up over a horse. But since everybody hated Ralph anyway, his death ends up being a good thing.

Christopher Moltisanti's (Michael Imperioli) longtime girlfriend and eventual fiancé Adriana (Drea de Matteo) catches the eye of many men. Tony Soprano looks her over and her FBI surveillance team ogles her playing tennis. But she makes many bad decisions, including letting a random woman into her inner circle which leads her to get entrapped into a position as an FBI informant.

The romance between Adriana and Christopher can only be described as tumultuous, marked by rampant drug use and the occasional domestic violence on Christopher's part. Then they make up and they're in heaven. Sure, Christopher cheats on her a lot but he truly seems to love her. So when he finds out she's an FBI informant, he's forced to choose between his loyalty to Tony and the woman he loves. Chris chooses the former.

Carmela also becomes close to Adriana and for the rest of the series she asks about Adriana's whereabouts. Of course it hits Christopher hardest and he never fully recovers, even after he's married and has a kid. It's good for Tony that he manages to eliminate another informant before she can pass on anything substantial, but it sends Christopher down a path of addiction and resentment he never recovers from.

Tony Soprano's cousin Tony Blundetto (Steve Buscemi) is released with several other mobsters, including the irascible capo Phil Leotardo (Frank Vincent) from New York's Lupertazzi family. While Phil is quick to get back into the business, Blundetto wants to try to make it as a civilian. Yet he still wants to live the gangster life, and drinking and gambling all night makes it tough to go to a real job in the morning. 

So Blundetto gets back into the life but he doesn't move up in the Soprano family fast enough. He starts working with one side of the Lupertazzi family's internal war, executing a New York guy. Phil and Billy Leotardo (Chris Caldovino) avenge this by killing the Lupertazzi capo who'd hired Blundetto and in a fit of rage Blundetto shoots Phil and Billy, killing the latter. This killing leads Phil to call for Blundetto's blood, implying he's going to do worse to Blundetto than just kill him. Tony finds his cousin in hiding and kills the man himself with a shotgun, in part to assuage New York and in part to save Blundetto a worse fate.

Soprano is forever pained by having to kill his own beloved cousin. Phil Leotardo, meanwhile, isn't satisfied and forever points to the killing of his brother by Blundetto to justify escalations between New York and New Jersey. Tony pays for the killing of Billy Leotardo, in one way or another, throughout the rest of the series.

Vito Spatafore (Joseph R. Gannascoli) had long been a top soldier for the DiMeo family, even serving under Richie Aprile before eventually becoming a capo for Tony directly. He's a good earner and loyal to a fault. He's so respected that when Tony ends up in a coma, Vito wonders if he'll become boss. There's only one problem — Vito is secretly gay in an old culture that sees homosexuality as an abomination. Plus he's married to Phil Leotardo's sister.

When Vito is spotted in a gay bar, he goes on the run. Phil Leotardo, acting Lupertazzi boss while Johnny Sack fights lung cancer in prison, demands Vito's death on the grounds that his sexuality is an insult to Leotardo's sister.

Tony doesn't really care about Vito's sexuality but Phil, a violent homophobe, wants Vito killed so badly that letting Vito live will lead to war with New York. Phil and two of his men end up killing Vito in a very crude and violent way.

This is an insult since a crime family isn't allowed to kill a capo in another crime family without approval — plus Vito was a top source of income for Tony in an increasingly-shrinking family.

Johnny Sack (Vincent Curatola), at the beginning of the series, is the underboss to Carmine Lupertazzi (Tony Lip), head of the New York Lupertazzi family. When Carmine dies there's a struggle between Sack and Little Carmine (Ray Abruzzo) for the control of the Lupertazzi family. Sack emerges as boss and spend much of his time showing Tony respect but unafraid to take a strong antagonistic position. Still, Johnny Sack is mostly level-headed and controlled, with an eye on the profits that come from cooperation with Jersey.

When Sack is diagnosed with stage 5 lung cancer in prison, Phil Leotardo starts running New York. After Sack's death, Leotardo decides to take on New Jersey. 

Johnny Sack's death in prison puts the angry, increasingly erratic Phil Leotardo into the top spot in New York, leading him to demand more and more from Tony before finally waging an all-out war, hurting both their businesses and resulting in the deaths of top guys in both families. It also makes Carmela afraid for her financial future after seeing the financial distress of Sack's widow and children due to his imprisonment and death.

Tony may have followed in his father's footsteps but, as will be shown in "The Many Saints of Newark," his uncle Dickie Moltisanti helped develop Tony Soprano into the mob boss he eventually becomes (it should be noted that "moltisanti" is Italian for "many saints," thus the title). In turn, when Dickie's young son Christopher begins coming up in the family, Tony holds the kid in special regard. 

Tony plays part caring uncle, part father figure to Christopher. At one point, Tony decides the only people he can trust are family and makes Christopher his main contact, to the chagrin of many who should have been ahead of the boy, specifically Paulie. Yet Christopher turns out to be almost as much of a disappointment as Tony's own son, the lazy and unmotivated A.J. Chris constantly acts like he's owed something, unwilling to accept paying his dues. Plus he likes the lifestyle more than the business.

Christopher makes a movie that's a direct insult to Tony, and his addictions make him unreliable. One night Christopher flips his SUV off the road with Tony in the passenger seat. Christopher reveals he won't pass a drug test and Tony decides this is the last straw. He holds Christopher's nose closed so the young man drowns in his own blood.

Ironically, for all the love, time, and attention Tony had spent on the kid, Christopher's death by Tony's hand seems to be a relief for the boss — who had come to see Chris as a liability.

Tony Soprano's relationship with Phil Leotardo was, at the best of times, an uneasy alliance. For most of Phil's rise to the top after his release from prison, Leotardo is like many of the other former prisoners in the series. He doesn't want to accept the growing power possessed by Tony. Leotardo has the extra chip on his shoulder of being from New York and having to make deals with Jersey, a mob family he considers inferior.

Leotardo is also hot-headed and emotional, easily blinded by his own perceptions of injustice and, as time goes on, increasingly egomaniacal. Eventually Phil chooses his own quest for vengeance and vindication over the financial and physical welfare of his crew. Butch DeConcini, Phil's underboss, grows increasingly unnerved by Phil's behavior. He has a sitdown with Tony and Paulie, agreeing to end the war and let Tony take out Phil. Phil Leotardo's death is one of the most unforgettable of the show — Leotardo is shot in the head at a gas station and falls down, his still-moving car rolling over his skull with an audible crunch as onlookers gasp and one even vomits.

Phil Leotardo's death in the final episode cements a peace between New York and New Jersey, leading a "happy" ending for the series — at least before the final scene.