Over the years Winkeler rose in the Capone gangs' ranks and by 1933 was running a lucrative nightclub and other ventures on the Northside. He was good friends with another hoodlum named Ted Newberry who tried to take out Frank Nitti and ended up going on a ride himself. The syndicate was bit wearing of Winkeler after that but didn't make a move.
Because of his former bank robbing exploits, the FBI, which was gearing up for its war on crime, started questioning Winkeler on a regular basis. With Capone behind bars, Nitti and his cohorts decided that Winkeler was a liability. As he was leaving a beer distribution plant, two men with shotguns cut him down.
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