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.
Recruited into Jigsaw's Crew
When Jigsaw decided to make a crew for himself he turned to a motley of various military veterans at McFeeney's, ultimately deciding to pursue a life of crime together, to which Jigsaw was the ringleader, one of the people recruited was Bobby.
Helping Jimbo Out
Despite his awkwardness, Jimbo managed to find a common language with Jake Nelson, Bobby and other 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 Jigsaw and others for help. When Jigsaw saw Jimbo's car being towed he let the tow-truck drive off and then orders Bobby and a fellow crew member José to follow the tow-truck while Jigsaw, Jimbo and Nelson would cut the tow-truck off. While Jimbo was distracting the driver by having to tie his shoes. Taking advantage of the situation Jigsaw, Nelson and Bobby got into the tow-truck and Jigsaw then decided to brutally beat the tow-truck driver before being stopped by Nelson. Jimbo then drove Jigsaw, Bobby and the other crew members out of there before Jigsaw told Jimbo to leave New York City and go back to Texas.
Training for the Robbery
Jigsaw had discovered that ReadyQuick Check Cashing was holding three hundred thousand dollars. After discovering this, Jigsaw had started to train his crew in hopes of prepping them to rob ReadyQuick. Jigsaw, along with Nelson and Geno had acted as robbers while the rest of the crew acted as victims of the fake robbery. While Jigsaw was distracted using fake restraints on a crew member Bobby attempted to take Jigsaw down, possibly in order to impress his fellow crew members, however Jigsaw manages to flip Bobby on the ground. Jigsaw then says to the rest of the crew how Bobby's actions were smart as he was trying to get Jigsaw while he was distracted.
Bobby, along with Jigsaw and Mike went over to rob ReadyQuick. Bobby is seen looking at Jigsaw while he he is telling the manager, Lillian to open the door to the money. When Lillian had refused to open the door to the money Bobby was shown to have a confused look on his face. Bobby then showed annoyance on his face when Lillian still had refused to open the door to the money. When Jigsaw had 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 opened the door to the money and the cashier's side Bobby ran in and then ordered Lillian, Reed and an unnamed female 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.
When the Punisher was attacking Jigsaw's crew and had managed to kill Mike and Geno Bobby had attempted to avenge Mike and Geno by shooting at the Punisher. While Todd, a fellow crew member was shooting at the Punisher 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 Reed's restraints, revealing that Reed was actually Jigsaw's inside man. Bobby was shown to be angered at Jigsaw, mainly due to Jigsaw not being able to move being the cause of Geno and Mike's deaths. 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 Reed and Bobby were both shot in the head by Jigsaw, killing them instantly. Reed and Bobby's deaths were used by Jigsaw to strike fear in the hearts of Bobby's fellow crew members so that they wouldn't doubt him, the method had worked in Jigsaw's favor.
- MP9: Bobby uses the sub-machine gun during the robbery, and used it to hold the hostage. He 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 Cash Checking. This was also where Bobby and Anton Reed would meet their ends.
- Lillian - Hostage
- Frank Castle/Punisher
- Curtis Hoyle
- New York City Police Department
- Billy Russo/Jigsaw † - Leader turned Killer
In chronological order: