Bobby managed to actually beat Tony by first sucker-punching him while Tony was insulting him and his wife and unlike all of Tony's other opponents, Bobby is one of the very few people in the series bigger than Tony.
A mobster, Bobby is first shown as a soldier and then later top aide to Corrado "Junior" Soprano. Throughout the series, he rises through the ranks of the organized crime organization, becoming a captain, as well as Tony Soprano's brother-in-law.
Bobby Baccala
It's always the quiet ones that are the toughest. Bobby doesn't love violence (he only kills one person the entire show) but he is the only man to ever beat Tony in a fight. And he does it to defend his wife's honor.
1. Tony Soprano. It feels like cheating to choose the protagonist and namesake of "The Sopranos" as its best character, but there's no way around it. Tony Soprano is not just the show's best character, he's one of the greatest characters in television history.
Bobby is undoubtedly the nicest mobster on the show. He is humble, shy, and takes all kinds of offensive jokes thrown at him. He doesn't tolerate disrespect to his family and that's the reason he brutally beats up Tony when he insults his wife.
Tony is angry with Janice when she tells a story that discredits their father. He makes a crude joke about her in return, apologizes, but then makes another. This provokes Bobby into punching Tony, leading to a messy and ferocious fight. Tony ends up on the floor, bloodied, unable to rise.
Tony Soprano and Christopher Moltisanti have a higher kill count than Paulie, due to their contributing actions to the deaths of many more characters. However, Paulie takes the lead over both characters by directly killing nine people compared to both Christopher's seven and Tony's eight.
Although the villains of The Sopranos mostly comprise other mob bosses, Tony's mother is the series' main overarching antagonist throughout the first three seasons. While Livia Soprano was killed off in The Sopranos season 3, the series originally...
Bobby won the fight, battering the inebriated Tony quite severely, but also injuring his boss's pride. Tony, although reasonably gracious in defeat, was embarrassed at having been beaten and frequently asserted to Bobby, Janice and Carmela that he would have won the fight had he not been drunk.
Peter Paul "Paulie Walnuts" Gualtieri played by Tony Sirico, is a caporegime (captain) and later underboss in the DiMeo crime family.
The Soprano Crew is a crew in the DiMeo crime family, being led, as of the start of the show, by Tony Soprano. It used to be led, and was presumably founded by Tony's father, Johnny before him, and Tony became captain of the crew upon his father's death from emphysema in 1986.
Bobby Baccalieri
Everyone could use a pal like Bobby Bacala. He's kind, warm, and friendly, a great dad, and eventually becomes a vital part of the Soprano organisation.
Paulie was a capo of the Soprano crew, within the DiMeo Crime Family - he was never officially an underboss (although Tony oft treated him as an unofficial third in command aka underboss).
The tragic tale of Adriana La Cerva (Drea de Matteo) was the saddest ending for any character on the show. The niece of Richie and Jackie Aprile, she was familiar with the temptations and perils of mob life and certainly didn't shy away from it.
After Tony's death in The Sopranos, perhaps Silvio regained consciousness. After several months of rehabilitation, he took responsibility for the entire family. Silvio claims he was discussed as a candidate for boss after Jackie died, and he did become acting boss at the beginning of Season 6 after Tony was shot.
Psychopath Ralphie arranged the hit at the prompting of Tony(who was ready to inflict a little payback after Jackie Jr. brokethe heart of his daughter Meadow).
Tony killed his closest friend when he found out Big Pu$$y Bonpensiero had turned states evidence against Tony and the DiMeo Crime Family. But, of the three listed in the question, it would probably be Silvio Dante who was Tony's closest confidant and best friend after Big Pu$$y.
As it turns out, several of Tony's closest allies betrayed him. However, the most consequential might be Carlo Gervasi. Carlo was a capo and top earner for Tony. In the series finale "Made In America," Tony discovers that Carlo became an informant and posed the greatest threat to Tony going to prison.
Tony is more of a tragic character than an evil one, and his tragic flaw is his extreme loyalty to his crime family, despite recognizing its moral flaws. This flaw however does not absolve him of his misdeeds. One of the characteristics often associated with an evil person is a lack of remorse for their actions.
Now that we have established Paulie's motives, here is how it went down: Paulie cut a deal with New York where he would arrange the assassination of Tony and declare himself the new boss of the DiMeo family.
Throughout the series and the many fights Tony gets into, the only one he ever loses is against his brother-in-law Bobby Baccalieri, who ironically is one of the nicest and least violent gangsters in the series.
While it ran for eight years, there were just six seasons; Chase didn't produce material for air in either 2003 or 2005, nor did he have any desire to overstay his welcome. In 2006, the network aired the first 12 episodes of a planned 21-episode final season.