Bobby Bacala, unlike many of his fellow wiseguys, was big-hearted and quite shy, and never kept a goomar, being entirely faithful to Karen and then Janice.
- His name is derived from real life New Jersey mobster Robert Bisaccia.
He ran Junior Soprano's old loan shark business. Although not officially a captain, Bobby was a high ranking soldier who ran Junior Soprano's interests as acting captain and reported directly to Junior, and more recently to Tony. Prior to his death, he was thought to be the heir to the job of boss, if Tony was whacked or arrested. Bobby was the son of Bobby Baccalieri, Sr. — also a mobster (Tony Soprano referred to him as "a real terminator", indicating his extensive record of mob killings) who fronted as a barber. Bobby's father returned from retirement for one last job before his death from lung cancer, which Bobby found quite distressing. Before joining Junior Soprano's crew Bobby was a head waiter until at least 1986 and was groomed by his father Bobby Sr. At some point, Bobby became a made man, although without making his bones; this may have been arranged by his father. Bobby was married to Karen Baccalieri until her death and they had two children, Bobby III and Sophia.
Bobby was quite different from the other men in the Soprano crime family. He was quiet, almost shy, sweet and even-tempered; these traits made him well-liked, if not necessarily respected. He was obese, which brought him much ridicule, but he was very loyal and even Tony apologized to him after making cracks about his weight. In turn, Bobby was always respectful, and sometimes affectionate, towards Tony, telling him "I always liked you," in the aftermath of a feud that saw Tony order the deaths of several members of Junior Soprano's crew, with Bobby and Junior the sole survivors. He bore no lasting grudges against Paulie Gualtieri or Christopher Moltisanti, who carried out these hits, and appeared briefly looking delighted on the day Christopher was 'made'.
Bobby operated Junior Soprano's loan shark business in his stead and also acted as Junior's assistant while he was under house arrest on federal racketeering charges. Junior eventually rewarded him by putting him in charge of his loan shark operation during the later part of his prosecution. Bobby was made acting capo when Junior had Murf Lupo step down in "For All Debts Public and Private".
Bobby was very loyal to his wife, Karen, and was the only made man in the Soprano crew without a comaré. The only time he was ever seen with another woman other than his wife was in the episode University. When Ralphie walks back into the Bada Bing after beating Tracee to death, Bobby could be seen talking to another stripper. However, Bobby lost his wife in a car accident and took it especially hard. Following Karen's death, Janice Soprano, along with many other women, actively pursued Bobby, trying to help him out as much as possible (with cooking and watching over Bobby's two children) but also trying to initiate a relationship with him.
When his grief continued, Janice went so far as to use the internet to expose his children to a Ouija board within their house. This frightened them and cleared a path for Janice to demonstrate that Bobby's grief was affecting his children. Despite Bobby's initial reluctance, the two were soon married and he soon fathered a daughter, Domenica. Bobby remained unaware of his wife's machinations at the start of their relationship. Bobby also enjoyed playing with model trains.
Since 2001, when he assisted Tony in rescuing Christopher Moltisanti and Paulie Gualtieri from the Pine Barrens, Bobby had grown closer to Tony. Additionally, as Ralph Cifaretto put it, "dating the boss's sister will help a made man's career"; nevertheless, Tony had recently stepped up his expectations of Bobby, whom he felt was taking their newfound family relationship as an excuse not to earn at a competitive level, compared to other members of the family. Bobby rose to the occasion by supplementing his income with $7000 he received for shooting a rapper he met at the hospital, while Tony was in the ICU, in order to raise the rapper's profile.
In the Season Six episode, "The Ride" Bobby's wife, son and youngest daughter were involved in a ride accident at the feast of St. Elzear while he took his other daughter to the bathroom. Bobby's initial reaction was relief that his family were unhurt. Janice berated him for not standing up for them at a later Sunday dinner at the Soprano residence. She later accompanied him when he paid a visit to the ride owner. Bobby stormed into his motel room, beat him up and tried to extort money from him but learned that Paulie Gualtieri had been responsible for withholding the funds needed to repair the ride. Bobby tracked him down at the festival and angrily confronted him - the two were separated by other associates in the crime family. At Christopher's belated bachelor party Bobby left soon after Paulie arrived. Tony ordered Paulie to make things right with Bobby. The episode demonstrated Bobby's devotion to his family, but also confirmed his credentials as a man not to be crossed lightly, further cementing his position in the higher echelons of Tony's crew.
In the Season Six episode, "Moe N' Joe", Bobby was beaten and robbed by a street gang as he was making his collections. One of the gang members fired a shot at the sidewalk near Bacala's face and a concrete fragment injured his right eye. The injury left his sight in the eye uncertain. Despite the injury, Bobby made certain his payments reached Tony, by way of a concerned Carlo Gervasi visiting Bobby at the hospital.
Bobby's injury prompted Tony to reassess his relationship with his sister and brother-in-law. Tony's feelings of guilt prompted him to broker an agreement with Johnny Sack that allowed Bobby and his family to buy Sack's house at half price.
In the Season Six Episode, "Soprano Home Movies", a drunken fist fight between Tony and Bobby, sparked by an obscene comment made by Tony about Janice, threatened to compromise the growing relationship between the two men. 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. As a partial result of this awkward incident, Bobby (to his visible discomfort) was tasked with murdering the brother-in-law of one of Tony's Québécois associates, an important hit that formed part of a deal to save money on a pharmaceuticals racket. It was Bobby's first murder; Tony mentioned earlier that Bobby had never "popped his cherry" with wetwork.
The murder initiated a change in Bobby's attitude from a soft and shy personality to a more outgoing, assertive and ruthless one. When his brother-in-law and boss Tony Soprano was having difficulties regarding a loan from loan shark Hesh Rabkin, Bobby suggested Tony not bother paying any of the money back considering Hesh could not force Tony to do anything. Such a ruthlessly logical piece of thinking was quite at odds with the gentle, quiet Bobby of a few years previously.
At the time of his death, Bobby appeared to have won a place within Tony's "inner circle" of trusted associates; no mean achievement for a man who, for a long time, had been little more than Junior Soprano's driver (as a dismissive member of Phil Leotardo's crew once described him).
In the episode "The Blue Comet" a war breaks out between New York and New Jersey. Phil Leotardo orders the deaths of Bacala, Silvio Dante, and Tony Soprano. Tony is informed by FBI agent Dwight Harris at Satriale's that a snitch in Brooklyn implied to them that Phil has ordered a major hit on the New Jersey crew. Tony then gives orders to inform everyone of the upcoming assassination plot. The scene then shifts to Bobby exiting his car going into a hobby shop, leaving his cell phone behind, while a call comes through most likely attempting to inform him of the assassination plots. Bobby goes in to check out a vintage train set, "The Blue Comet" while the storekeeper talks to him. Two men are seen entering the store and open fire as he's purchasing the set. Gun shots break out throughout the store sending his rattled body crashing on top of the train display. Later in the episode, when Tony is reflecting on Bobby's death, holding the assault rifle that Bobby gave him on his birthday, Tony flashes back to the moment when he and Bobby were fishing, contemplating their own fates. Bobby observes that when getting killed, you "probably don't even hear it when it happens, right?"
Rank: Soldier (eventually made into a Capo after the acquittal of Junior Soprano's RICO trial and then finally Tony Soprano's Underboss.)