After Sly Cooper and Bentley destroyed Octavio's Ferris wheel, which was secretly pumping tar into the surrounding waters, Octavio had Tony and the rest of the guards start keeping tabs on each other by asking for specific passwords whenever they interacted. He also ordered Tony and several other guards to guard the entrance to his coffee houses in shifts, as the blueprints to his tar-pumping operation were hidden inside them.
During the mission "Guard Duty," Tony guarded the coffee house next to the police headquarters. Unlike the other guards, who trusted anyone wearing a guard's uniform that could relay a password, Tony believed that he was a notable enough member of the mafia to take the test a step further. He decided that when the next guard showed up to take his shift, he would also ask the guard what his nickname was; the answer was Tony "The Killer" B. The next guard that approached him was Sly in disguise. When Tony asked Sly to provide his nickname, a flustered Sly managed to find a way to postpone the conversation and left Tony's sight. Sly eventually returned and told Tony what the nickname was, causing Tony to leave his post.
Tony is a narcissist, often boasting about his supposed importance in the mafia. Unsurprisingly, this annoys many of his peers; one of the guards described him as an egomaniac to a disguised Sly, while another referred to him as a fathead and an idiot. His boasts seem to be over-exaggerated; while he claimed that most guards should know his nickname because of how famous he is, the responses Sly got from the guards about Tony implied that the nickname was self-proclaimed and that many of the guards do not know his nickname. This would put his claim of being "the mayor of organized crime in Rome" into question.