Gus Winkler

October 9, 1933

The American Boys

Gus Winkler was a safe-cracker, torpedo and freelance hood during the days of Prohibition. The highlight of Winkler’s criminal career was undoubtedly becoming a pal of Al “Scarface” Capone. Though Gus was considered a gutless wonder, he’d somehow made it into Capone’s good books and was used by the mob boss for special cases, including the assassination of Frankie Yale and that hit of all hits, the St. Valentine’s Day Massacre.

Starting out in the St. Louis gang Egan’s Rats, Winkler hooked up with Fred “Killer” Burke and Bob Carey. When things fell apart for the Rats in 1924, Winkler ended up in Chicago, by way of Detroit. It was some time during this period that he lost an eye during a mail robbery. A vain man, Winkler hoped to polish his image and took to wearing glasses in order to camouflage the disfigurement.

Winkler, Burke and Carey came to the attention of Al Capone at this time, doing some priority jobs for him, most notably that big one in 1929. Capone referred to them as “The American Boys”. But the gang were enterprising and pulled numerous heists on their own, holding up armoured cars and robbing banks in New Jersey, Wisconsin, Los Angeles and Ohio. Revenue from these robberies would allow Winkler to act as something of a gangland broker for criminal enterprises and to open an underworld safe-house for mobsters on the run.

Winkler was described as self-obsessed and somewhat talkative, and it was undoubtedly this chatty quality that would later get him into trouble. The end came for him on October 9, 1933, when he was shot down on Roscoe Street. Though, as in the case of so many others, Winkler’s killers were never identified, the truth is that the assassins could have been just about anyone in the syndicate. Winkler, trusted by no one, had made it perfectly clear on more than one occasion that he was out for himself no matter what. Though he’d apparently enjoyed a certain amount of protection from Capone, once Scarface was sent up the river, the new boss of the Chicago Outfit—Frank Nitti—had no use for Winkler.

Suspicion about the death has also fallen on Roger Touhy and his Chicago gang. In December 1932, Winkler participated with the Touhy mob in a mail robbery worth $250,000. Winkler himself had worried that the gang was after him because he hadn’t divided the loot to their liking.

A mugshot of Gus Winkler, courtesy of the Chicago Police department.

Dangerous memoirs

In any case, on that day in October, Winkler went down and he went down hard—a total of seventy-two bullets and buckshot pellets had passed through his body, ensuring that he would never get up again. And Winkler’s link to the St. Valentine’s Day Massacre? It was his wife, Georgette, who later revealed his connection with that epic slaughter. During Winkler’s criminal career the blonde and beautiful Georgette had acted as his right hand, often vetting his contracts. After his death, Georgette attempted to publish her memoirs—a work that outlined her husband’s relationship to the mob. But the piece was considered too hot at the time and remained unpublished until its discovery several years ago, when it blew the lid off the massacre.