In 2001, a petty criminal named Claude is betrayed by his girlfriend Catherine during a bank robbery on the outskirts of Liberty City. Left for dead, Claude is arrested, but escapes during his transfer to prison when members of the Colombian Cartel ambush his transport to kidnap another prisoner. During his escape, Claude befriends the 8-Ball bomb expert, who introduces him to the Leone Mafia family. Working for several members of the Leone family, Claude finally earns the respect of Don Salvatore Leone who, upon discovering that the Cartel is manufacturing a new street drug that funds his operations, orders Claude to destroy it with the help of 8- Ball.
Soon after, Salvatore asks Claude to take care of a minor problem, but his trophy wife, Maria, reveals that it is a trap. Claiming that Salvatore has become paranoid and is trying to kill him, Claude escapes with her to Staunton Island. Maria introduces Claude to the Yakuza, led by Asuka Kasen and her brother Kenji, who assign him work after he assassinates Salvatore, effectively severing his ties to the Lions. During this time, Claude also works for corrupt LCPD detective Ray Machowski, whom he later helps to flee the city, and media mogul Donald Love, who orders an attack on Kenji under the guise of a Cartel attack, to start a gang war that will allow him to secure real estate for his businesses. Finally, Claude meets Catalina at a construction site during one of Love's jobs, only for her to escape.
