there are nearly 0 reliable sources about aiuppas wild years, because his first arrest was in 1935 for suspicion of attempted murder.
he was most probably a heavy hitter (connected to dillinger and the karpis gang) and was known for controlling gambling in cicero and suspected by the fbi as prostitution-kingpin aswell. from 1930 onwards he owned numerous clubs and gambling joints
He had several run ins with the law in the early 30s.
Dec of '33 he was indicted as a co-conspirator in the TNT shakedown(Trucking n Transportation). They were extorting coal yards by holding up deliveries. At that time he was an official with Teamsters local 782 Maywood and had O'brien listed as an alias.
In Jan 0f '34, a Joseph Aiuppa was picked up and released in Bellwood as a suspicious character in the vicinity of the house the cops were killing Handsome Jack Klutas in.
In May of '35, in a retrial he was found not guilty of the TNT charges.
June of '35 were the assault with intent charges in Berwyn, which were dismissed. Two days later he was picked up in Oak Park on general suspicion.
In Aug he would be picked up as part of a group suspected of robbing country clubs. He would be released when he told the cops he worked for Johnny Moore (AKA Claude Maddox) Three of the guys picked up with him (including an 18yo Rocco Pranno) would confess. All three were also suspected of robbing the Villa Park Bank.
This gives me the impression that he was definitely on the police radar at the time and already had enough clout to wiggle out the charges.
