Bob, as a CIA agent, was designated by his bosses for an operation called "Dead Head," which involved overthrowing the Hammerhead from power, as he was the leader of the international crime syndicate known as "Maggia". This and other such missions were all that were keeping Bob from returning to prison after he had failed the agency in the past.
To be able to enter the target's criminal circle, Bob allowed Bruno, Hammerhead's chief security officer, to rape him multiple times so that Bruno would keep him around. However, despite his sacrifices, his assistant, Deadpool, has always followed the plan the wrong way, hampering Hammerhead's assassination, after killing six of his agents and hiding in the basement after hangover with the maid.
When he saw that he was in danger of life, after Bruno finally discovered his plan, Bob caused Hammerhead to kill him, just as Deadpool arrives and murders everyone, including Hammerhead. After the mission was completed, Bob talks to Blind Al about Deadpool, talking about how dangerous and self-centered he is, and Blind Al ordered Bob to continue working with Deadpool as long as he got the results they needed, leaving Bob stupefied.
Bob continued managing Deadpool as his handler, through many hardships, manipulating Deadpool where necessary until his relationship with the CIA became strained and they framed him as a terrorist.
On Christmas Eve Wade managed to temporarily convince the world that Bob was dead, as part of a 'night before christmas' type plot to show Bob what the world would be like without him, and together they infiltrated the CIA headquarters at Langley, Virginia dressed as Santa. They then followed Blind Al to her home to find her mourning Bob as she now couldn't use him in her schemes. A trip to Cable's secret lair in Kabul where Colleen Liu very briefly mourned Bob before Cable comforted and distracted her with sex. They next visited Bob's childhood home where his parents celebrated his death as it brought them government death benefits. On Christmas day then visited Inez Temple at the institution she had been committed too and believed herself to be Santa. Bob then came to believe that the world might not need him but Wade did or he'd wind up dead.
Bob would go on to work with Deadpool in a more even partnership as they took down Cable and Bob's ex-girlfriend Colleen Liu who were really responsible for the attack that the CIA framed Bob for as they were the ones who sold the chemical weapon. Bob upset Colleen and realised they couldn't give them the information they needed so they instead went after the CIA after having to deal with a killer sent by Inez Temple and then Inez herself who provided them with the information they needed to get to the CIA. Bob and Deadpool raised forces to storm the CIA facility responsible for brainwashing Deadpool and others but were betrayed by Cable and Colleen who was in fact Inez in disguise. After this they were forced back into working for the CIA but Deadpool had triggered a bomb left in the facility which destroyed it with Inez and Blind Al inside.
Powers and Abilities
Some combat, weapons and espionage training