Tony Soprano was quite the social guy and as a result, he had more friends than enemies. Most of his pals came from within the DiMeo Crime Family but he had strong ties outside too. He even had law enforcement officers as allies, something which helped keep him out of prison during his reign as boss.
Being Tony’s friend was beneficial to anyone in the underworld since the New Jersey don was never too kind to anyone who appeared to detest him. While most of his friends were fan-favorite characters, a few were hard to tolerate. But despite inducing abhorrence among viewers, they were great characters nevertheless.
Detective Vin Makazian
Vin carried with him all the tropes of dirty cops. He was far from likable but he gave Tony one of the most important pieces of information—Sal “Big Pussy” Bonpensiero was an FBI informant. Big Pussy was part of Tony’s inner circle and he could have ultimately taken down the boss if his secret activities had never been discovered sooner.
Apart from that incident, most of the other things that Vin did were abhorrent. He tried too hard to please Tony, going as far as to beat up Dr. Mefli’s male companion because he thought the therapist was the don’s mistress and she was cheating on him. He also frequented illegal brothels in New Jersey, something that led to his downfall as he was arrested and jailed.
Tony and Christopher’s friendship started off well before plummeting into irredeemable territory. And it was mostly Christopher’s fault. At the start of the series, Tony had high hopes for the young mobster. He saw him as a future boss of the family and often confided in him things that he kept from other associates. Unfortunately, Christopher kept letting him down.
He insisted on pursuing a film career, even though Tony was against it and kept sinking deeper and deeper into drug addiction. Whereas Tony refrained from sleeping with Christopher’s girlfriend Adriana when he had the opportunity, Christopher began seeing Julianna Skiff in secret, a woman that Tony developed interest in first. The friendship would end tragically when a paranoid and angry Tony killed Christopher for crashing a car they were both in because he was driving while high on drugs.
The only reason this friendship was ruined was due to Tony’s own selfishness. After Hesh gave Tony a $200,000 bridge loan to help him make up for a string of gambling losses and dwindling income (his highest earner Vito had been murdered), Tony failed to repay in time. Instead, he began berating Hesh.
Before that, Hesh had been nothing but good to Tony. He gave Tony much-needed advice when he became estranged from Dr. Mefli. He also helped Tony solve a dispute with the Teitlemanns, over the ownership of a hotel. This friendship could have stood the test of time if only Tony was honorable.
Agent Dwight Harris
Harris wasn’t a big fan of Tony Soprano at first. The FBI agent was keen on taking down the New Jersey. It was his job after all. In Season 2, he orchestrated the perfect plan in which his junior agents bugged Tony’s house while everyone was away. He continued hunting Tony until he was transferred to the FBI’s counter-terrorist division.
At that point, he and Tony became close. Harris figured he could use the mob boss to acquire information since he mostly interacted with criminals. He thus requested Tony to let him know in case he came across any terrorist-related activity. In return, he’d put in a good word for him in case he ever got arrested. Harris even warned Tony about plans by the New York crew to whack one of Tony’s subordinates.
The Capo was undoubtedly one of the most enthralling characters in the show. Apart from having the strongest accent, he whacked more people than anyone else. He was cautious too as he never became a victim of the same violence he meted out. But even though he was part of Tonny’s inner circle, there were several moments that proved their friendship wasn’t so strong.
In Season 4, Paulie showed a lack of loyalty by trying to switch over to the Lupertazzi Crime Family when he felt Tony was snubbing him. And when Tony was in hospital after getting shot by Junior, Paulie tried money that he was supposed to pump up to the boss. But even with the misdemeanors, it was hard not to like Paulie.
Had Johnny Sack remained the head of the Lupertazzi Crime Family, the relationship between New York and New Jersey wouldn’t have become as volatile as it ended up being during Phil Leotardo’s reign. Sack trusted Tony even more than members of his own family, even confiding in him about his planned hit on Carmine Lupertazzi.
Sack was also less violent compared to other mobsters. Whenever he wanted to kill someone, it was for a very legit reason, like when Ralph made fun of his wife’s weight. The fact that Tony and Sack frequently met alone in less crowded areas proved just how much they trusted each other. Audiences could feel the pain too when Sack got jailed and eventually died of cancer.
Jackie Aprile, Sr.
Jackie and Tony came up the ranks of the DiMeo Crime Family together and became “made guys” at around the same time. Jackie’s ambition made him rise up the ranks quickly and he eventually became boss, much to Junior’s dismay. Though his reign was short-lived due to illness, it’s described as the most peaceful.
While he was ailing from cancer, Jackie made Tony the street boss. Unfortunately, Jackie succumbed to the disease.
He is the only person to ever defeat Tony in a fight, and the boss kept making excuses for the loss for ages. Apart from that one disagreement that resulted in fisticuffs, Tony and Bobby were mostly on good terms. The fact that Bobby married Tony’s sister, Janice, kinda helped in cementing their relationship. Before that, Bobby had been Junior’s guy.
Bobby was the nicest out of all mobsters in the crew. He was never on bad terms with any member of the family. At home, he was a good husband and father. He was allergic to bloody violence too as he only killed one person the entire series and that was because he was forced to do so.
Tony and Vesuvio owner Artie Bucco had been friends since childhood, having attended the same elementary school. The restaurateur was the only person Tony would argue with without getting physical. Even when Artie disrespected him, Tony maintained his cool, proving just how much he cared about him.
The two also had some sort of loyalty between them. Whenever Tony dined at another restaurant, Artie would be enraged. Though he was emotional, Artie was very social with guests and treated each of Tony’s associates with respect. As a result, their friendship remained strong from the start to the end of the series.
The DiMeo Crime Family consigliere established himself as a fan-favorite character from very early in the series when he entertained his colleagues by imitating Michael Corleone from The Godfather. He was also the most fashionable mobster in the New Jersey crew, often donning expensive suits at all times.
Silvio was the only person that Tony had full trust in and there was a good reason for that. The consigliere’s counsel came in handy on several occasions such as Ralph and Richie’s recklessness as well as Tony Blundeto’s unsanctioned hit. At times Silvio didn’t even need to talk. He’d simply give Tony “the stare” to let him know he was being an idiot and it worked.