Torrio controlled the Chicago crime world until when he decided that it was far too dangerous of a life to live, and he left the power to his protégé, Al Capone (Coffey).
Al Capone was perhaps the most famous and influential person in the country during the late 1920's. Although Capone was well aware that everyone knew that he was the new mob boss in Chicago, he was still very image conscious and generous. This was evidenced when he said, "I'll bet I've given a million dollars. I'm just saying this to show that I'm not the worst man in the world-. However, Capone's most recognizable trait was his cruelty and heartlessness. Capone would do anything to achieve his business and personal goals. One specific incident was the St. Valentine's Day Massacre. On Valentine's Day 1929, some of Capone's henchmen, some dressed as policemen, caught members of a rival gang in a warehouse where they were supposed to be picking up a hijacked truckload of whiskey. Seven of the rival gang members were lined up against a wall and shot repeatedly by machine guns. There were never any convictions in these murders (Cohen). Capone went on the make millions of dollars bootlegging alcohol. He was able to avoid any sort of criminal convictions in Chicago because he had dozens of police officers, politicians, and judges on his payroll. Those not on his payroll were often fearful to testify against the brutal Capone for fear of the possible backlash by Capone. However, in 1931, Capone's reign as mob boss in Chicago ended when he was convicted in federal court of tax evasion and sentenced to eleven years in federal prison, which were served in the toughest prison in the country, Alcatraz.
Al Capone was not the only successful alcohol bootlegger in Chicago, criminal defense lawyer George Remus was arguably as successful as Capone. Remus's legal experience allowed him to find a loophole in the Volstead Act.