In 1499, Il Bruto was hired by Armilia Guardato to aid in her plot against the House of Auditore, stealing a cache of munitions belonging to them. Guardato and Il Bruto despised one another but she paid him well. After a discussion in his stronghold in the hills below Mount Vesuvius, Guardato left for Naples to inspect the Auditore assets in Naples and tasked Il Bruto to get rid of the interlopers and bring her the head of Claudia Auditore.
Claudia and some allies infiltrated the stronghold and managed to reach Il Bruto, who did not want to fight them, since he believed that attracting the ire of the Brotherhood would cost him more than what Guardato paid him. He informed them of Guardato's deal with the Templars: in exchange for making sure the munitions would not reach the Italian Assassins' efforts to break Rodrigo Borgia's power in Rome, she would gain control of Naples. He also pointed them to the entrance of a secret Guardato warehouse, where both the munitions and Armilia would be hiding.