Bobby was a United States Army veteran and a member of Jigsaw's Crew, who had instigated and later participated as a gunman in the Robbery of the ReadyQuick Check Cashing. After announcing he was going to desert the crew, intimidated by the Punisher's interference with the crew's recent criminal activities, Jigsaw instead betrayed and killed him.
Bobby served within the United States Army before his discharge and return to New York City. There, Bobby befriended other fellow veterans, such as Jake Nelson, José, and Jimbo, with whom he used to drink at McFeeney's. Later, they were joined by Billy Russo who was invited to drink together by Nelson.
Helping Jimbo Out
Bobby joined his friends at the McFeeney's, where Jimbo, despite his awkwardness, managed to find a common language with fellow veterans, making them laugh. While drinking with them, Jimbo found out that his car where he lived was towed, much to his horror. He returned to the pub where he asked Billy Russo and others for help. When Russo saw Jimbo's car being towed he let the tow-truck drive off and ordered Bobby and José to follow the tow-truck while Russo, Jimbo, and Nelson would cut the tow-truck off.
While Jimbo was distracting the driver by having to tie his shoes, while Russo, Nelson, and Bobby got into the tow-truck and brutally beaten the driver before Russo was stopped by Nelson. Jimbo then drove Russo, Bobby and the other crew members out of there before Russo told Jimbo to leave New York City and go back to Texas. Bobby afterwards proposed to the rest of the crew that they should expand their criminal operations with a heist.
Training for the Robbery
- "Why did you choose a blue luchador mask?"
"Latex allergy, asshole."
- ―Todd and Bobby
Bobby had discovered that ReadyQuick Check Cashing was holding three hundred thousand dollars and recommended Billy Russo to rob it. Russo then recruited Mike, Todd, Geno, and Anton Reed to their crew, so they started to training for the robbery. Russo, along with Jake Nelson and Geno had acted as robbers while Bobby and the rest of the crew acted as the hostages. While Russo was distracted, Bobby attempted to punch Russo, intending to impress the crew, however, Russo managed to flip Bobby on the ground. Russo then says to the rest of the crew how Bobby's actions were smart as he was trying to get Russo while he was distracted, but Bobby was not so pleased by this.
- "Lillian, you're making me kinda nervous. Your behavior, it's erratic, it's irrational. Like you could do anything at any time without reason. Anybody else getting that same vibe off of Lillian, or is it just me?"
"She's a crazy old bitch."
- ―Jigsaw and Bobby
Bobby, along with Jigsaw and Mike went over to rob the ReadyQuick Check Cashing. Holding the hostages at the gunpoint, Bobby was looking at Jigsaw while he is telling Lillian to open the door to the money.
When Lillian had refused to open the door to the money, Bobby was quite confused and annoyed by her decision. Jigsaw then asked if anyone else in the bank had gotten the vibe that Lillian was irrational and unreliable, in order to back up Jigsaw's claim so that Lillian would open the door, Bobby called Lillian "a crazy old bitch" to which Jigsaw responded with "We don't like crazy".
When Anton Reed, who was their inside man, opened the door to the money and the cashier's side Bobby ran in and then ordered Lillian, Reed, and another cashier to line up on the wall so that Jigsaw could restrain them. Bobby then joined Mike with robbing the remaining cash in another room not seen on-screen. Mike and Bobby come out after they had successfully gotten the rest of the money, Bobby, Mike, and Jigsaw leave and take Reed with them as well.
- "Billy, now! Move!"
- ―Bobby to Jigsaw
When the Punisher was attacking Jigsaw's Crew and had managed to kill Mike and Geno, Bobby had attempted to shoot back at Castle. While Todd was shooting at Castle, Bobby ran over to Todd's car and got in. Bobby escapes when Todd drives off in his car with Bobby in it.
Departure and Death
When the rest of Jigsaw's Crew came back to their hideout, Bobby cut off Anton Reed's restraints. Bobby was shown to be angered at Jigsaw, mainly due to he was not able to move in front of the Punisher, which caused the deaths of Geno and Mike. Reed was shown to have agreed with Bobby and was even going to cut his ties with the crew due to the fact that Jigsaw had gotten two of his own men killed. However, before Bobby and Reed could leave, Russo shot them both in the heads, killing them instantly.
- MP9: Bobby uses the sub-machine gun during the robbery, and used it to hold them hostage. Bobby later used this briefly while engaging the Punisher and New York City Police Department officers.
- Jigsaw's Hideout: Bobby, along with the rest of Jigsaw's Crew went into one of the warehouses in Queens, in which the gang used to train to rob ReadyQuick Check Cashing. This was also where Bobby and Anton Reed would meet their ends.
In chronological order: