The Sopranos: Tony’s 10 Most Dangerous Enemies
Things are rarely peaceful in the DiMeo crime family. Tony Soprano himself has had to face some dangerous enemies in his life.
The Sopranos began its eight-year run on HBO over two decades ago. The series, centered on a family involved with organized crime in New Jersey, has remained the crown jewel in the world of anti-hero dramas, largely due to the singular performance by James Gandolfini as the main character, Tony Soprano.
Tony, his real family, and his mafia family go through myriad battles over the course of six seasons of The Sopranos. Things are rarely peaceful in the DiMeo crime family, both due to external and internal threats. There are quite a few villains that threatened to knock Tony off his perch as boss, but here are ten of the most dangerous ones.
Sal Bonpensiero
Tony has several FBI informants in his crime family throughout The Sopranos. The one that was most devastating to him was Sal Bonpensiero, due to their close personal friendship.
Tony did what he could to try to help his friend after he began to suspect that he was working for the FBI, but the information that Bonpensiero divulged and had at his disposal was too big of a threat for Tony to ignore. He had to take him out, which haunted him for years. Friends become enemies very easily on The Sopranos.
Ralph Cifaretto
Ralph Cifaretto was one of the most universally-hated members of the DiMeo crime family. His treatment of women, even in the realm of hyper-toxic masculinity that he resides in, is extreme. He also has a tough time holding his tongue when he should show respect towards others, like he failed to do when making an off-color joke about the wife of Johnny Sacramoni, a high-ranking member of the Lupertazzi crime family.
This joke had far-reaching consequences that Tony and the rest of his crew had to deal with. Tony eventually had enough of Cifaretto, specifically after he suspects he burned down a stable full of racehorses in order to collect the insurance money. Tony kills him in one of the most brutal scenes of the entire show.
Richie Aprile
Richie Aprile never really respected Tony. He does not know Tony as the boss of the DiMeo family, for he has been in prison since before he took that position. This leads to insubordination. Richie simply cannot take commands from the kid he used to order around when he was growing up, and Tony can not afford to have an undermining presence in his family, for it reflects poorly on him.
Richie fancies himself a more suitable man for the title of boss, and starts to put a plan in action to take Tony out. Tony is also planning to take Richie out, though both schemes are nullified when Tony’s sister and Richie’s fiancée, Janice Soprano, murders Richie in the middle of an argument.
Corrado “Junior” Soprano
Corrado Soprano is Tony’s uncle from his father’s side. The beginning of The Sopranos is highlighted by Tony and Uncle Junior’s power struggle to become the new boss of the DiMeo family, after the death of Jackie Aprile. Though Tony eventually wins that battle due to Junior’s incarceration and his lesser reputation within the family compared to Tony’s, Junior is a consistent threat.
His plan to have Tony murdered nearly works, and he later puts a bullet in his nephew himself, although he was not in the right frame of mind when the latter occurs. No matter what state he is in, Tony has to watch out for his uncle, for he knows how to get under Tony’s skin and is willing to go to extreme lengths to get what he wants.
Livia Soprano
The root of many of Tony Soprano’s personal issues. Livia Soprano is Tony’s mother, who is a constant, nagging, demeaning, and inconvenient presence in his life. While she starts out as simply a curmudgeon, Mrs. Soprano shows just how far she is willing to go when she helps orchestrate a plan to take out her son.
She is upset at him for a variety of reasons, mainly for putting her in a nursing home. Mrs. Soprano is well-versed in the mafia way of life, so she knows what it means to eliminate a problematic member of the family. She was indeed willing to have her own son killed.
Johnny Sacramoni
“Johnny Sack,” as he is called, eventually becomes the boss of the Lupertazzi crime family, out of New York. Although he is an old friend to Tony on the surface, his immense power allows him to gradually infiltrate the DiMeo family, gaining inside information about their business dealings and their plans to undermine him in various ways.
What’s more, “Johnny Sack” is a very proud man, whose insecurity makes him unable to handle even the smallest perceived slight. Sacramoni does not mind putting hits on members of the DiMeo family, including Tony himself, if he feels it is appropriate. Were it not for his prison sentence, he might have eventually been the source of Tony’s undoing.
Phil Leotardo
Johnny Sacramoni’s sidekick. Phil Leotardo, like Sacramoni, is willing to take people out if necessary. However, while “Johnny Sack” is cunning and political in his exploits, Leotardo is a sledgehammer. He is old-school when it comes to mob justice, something that is quite threatening to Tony’s livelihood after Leotardo becomes acting boss of the Lupertazzi family.
Leotardo doesn’t negotiate; he takes what he determines is his, which is quite a lot, as he feels he has paid his dues in prison and now has no reason to make concessions to anyone. This is the last villain that Tony faces before the show reaches its conclusion, and the bloody battle between them nearly ends both families.
Frank Cubitoso
Tony’s threats not only come from mafia-related dealings, but also from the FBI. The orchestrator of those issues is Chief Frank Cubitoso, whose goal is to bring down the DiMeo family by gaining intel of their criminal activities.
He does this by bugging Tony’s house and threatening the fiancée of Christopher Moltisanti, a DiMeo captain, with jail time, which forces her into becoming an informant for the FBI. Tony is tough to pin down, however, and he eventually slips through the fingers of Chief Cubitoso and his team.
Butch DeConcini
Butch DeConcini is introduced late in The Sopranos, but he makes his presence felt. He is an underboss of the Lupertazzi family, though he clearly has ambitions of being the head of the entire crime syndicate.
DeConcini is a manipulator, who seems to be on Phil Leotardo’s side as he plans to wipe out the DiMeo family, yet is willing to sanction the hit with on Leotardo with Tony after he sees an opportunity for him to ascend to the highest position. The ending of The Sopranos is highly-debated, but if you assume that Tony is killed in the diner, it would make sense that it was DeConcini, the new head of the Lupertazzi family, that planned this final act to further solidify his power over the area.
Tony Soprano
That’s right. Tony Soprano’s most dangerous enemy is often himself. Tony has a litany of psychological and emotional problems, stemming from certain events in his childhood and the immense pressure that comes with being the boss of a mob family. He seeks help for these issues, but they are never truly solved.
Many of Tony’s failings are a direct result of his temper, insecurity, selfishness, and paranoia, which he is unable to rid himself of. “Uneasy lies the head that wears a crown,” as Shakespeare said.
