Prohibition-era
McLain took a run-in with a few Purple Gang members, They were fighting with him telling him that it was a Jewish area. One of them pulled a gun and shot at him. Both of them missed, but hit and killed his girlfriend.
McLain got back at the Purple Gang with the help of Jack "Machine Gun" McGurn. He started work in McGurn's speakeasy, the Green Mill, as a bartender. He later became involved with McGurn's crew inside the Chicago Outfit which at the time was run by Johnny Torrio and Al Capone.
McLain helped McGurn kill Frankie Yale in 1928.
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