By 1930, Roger Touhy and Matt Kolb were millionaires. Their small, but profitable beer and gambling empire stretched from midtown Chicago to as far north as St. Paul, Minnesota. They owned dozens of speakeasies, roadside casinos, handbook parlors, three large breweries, and an enormous fleet of trucks. Roger saw repeal approaching and invested his earnings in a dry cleaning business with Kolb's brother, commercial real estate, a well digging company and a winter place for himself in Florida. Unlike Matt Kolb or even his own brothers, Roger intended to be completely legitimate by 1933. Then he and Clara and their boys would sell everything and move west to Colorado, although Clara was holding out for Florida.
However, if Touhy was ready for prohibition to end, the mob wasn't. The depression hurt more and more of the mob's traditional enterprises like prostitution and gambling. A1 Capone decided to take over Chicago's labor racket business and gain control of the Teamsters International strike fund, worth an estimated $150,000,000 with another $10,000,000 a year flowing into its coffers from membership dues.