With the failure of Mayor Dever's reform program, the rise of Chicago as the imperial gangster city became the most significant campaign issue in the 1927 election. "Big Bill" Thompson, assisted by a small fortune in campaign funds from organized crime, came back into power. It looked as if the bad guys would have the city in their grip forever.

However, a few tiny blips on the radar screen showed some promise to eventually make a major impact on the city of Chicago, the bootlegging business and Al Capone. In May of 1927, the Supreme Court made a decision that Manny Sullivan, a bootlegger, had to report and pay income tax on his illegal bootlegging business. Just because reporting and paying tax on illegally-derived revenues was self-incrimination, it was not unconstitutional. With the Sullivan ruling, the small Special Intelligence Unit of the IRS under Elmer Irey was able to go after Al Capone.

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Unaware and uninterested in Manny Sullivan or Elmer Irey, Capone became more compulsively extroverted and expansive. He indulged heavily in his two big passions, music and boxing. He became close pals with Jack Dempsey, but given the concern over fixed fights, the friendship had to be very discreet. Always an opera lover, Capone expanded his patronage to the jazz world. With the opening of the Cotton Club in Cicero, Al became a jazz impresario, attracting and cultivating some of the best black jazz musicians of the day. Unlike so many other Italian gangsters, Al did not seem to have the deep-seated racial prejudice and he gained the trust and respect of many of his musicians. Al extended his generosity and personal concerns to everybody who worked for him, black or white.

Bergreen describes the way Capone inserted himself into the lives of those he knew: "He came to dominate them not by shouting, overwhelming, or bullying, although the threat of physical violence always loomed, but by appealing to the inner man, his wants, his aspirations...by making them feel valued, they gave unstintingly of their loyalty, and loyalty was what Capone needed and demanded; in the volatile circles through which he moved it was the only protection he had from sudden death. The highest compliment other men could pay Capone was to call him a friend, which meant they were willing to overlook his scandalous reputation, that he had never been a pimp or a murderer."

"Public service is my motto," Al told reporters around Christmas. "Ninety percent of the people in Chicago drink and gamble. I've tried to serve them decent liquor and square games. But I'm not appreciated. I'm known all over the world as a millionaire gorilla." The exposure was becoming a real nuisance. When he left for a trip to the West Coast, he had police surrounding him at every station. Los Angeles' toughest detective said "We have no room here for Capone or any other visiting gangsters whether they are here on pleasure tours or not."