As a young adult, Michael eventually became a criminal. According to Michael, he had been in prison twice by the time he was 20. He committed his first robbery in the outskirts of Carcer City in 1988, where he managed to steal $10,000 from a small franchise. While in prison, Michael learned many skills, including learning how to use a tattoo gun by tattooing his name on his cellmate's buttocks. Despite his failures and shortcomings, Michael perfected his criminal skills to the point where he became an expert marksman and efficient leader amongst other things. During this time, he associated himself with Lester Crest, an exquisite planner that would later assist Michael in planning out heists, as well as other tasks.