He was first arrested in 1925, for auto theft. He soon graduated to "triggerman", and by the age of 20 had been the prime subject of three murder investigations, but never tried for any of them.[2] During the late 1930s, Giancana became the first 42er to join the Chicago Outfit. From the early 1940s through the 1950s, he controlled most of the illegal gambling, illegal liquor distribution, and numerous other political rackets in Louisiana through longtime friend H. A.