Feature Articles

By John William Tuohy

     "Smiling" Gus Winkler's motto was "Take care of Winkler first" and he had spent most of his criminal career doing just that.

     The day before somebody slammed 72 bullets into him, Winkler was seen in the FBI's Chicago office in the Bankers building, in a meeting with Special Agent, Melvin Purvis.

     Whoever it was that spotted Winkler talking with the Feds spread the word and somebody took care of Gus Winkler.

     Gus Winkler, good natured, smart and smooth, had started out as a member of Eagan's Rats, and, by age 20, he was a safe-blower of some note. He did time from 1920-26 for assault and wounding with a deadly weapon. After he served his time, Winkler decided it was best to leave St. Louis and head for Chicago. Once there, he struck up a lifelong friendship with Fred "Killer" Burke, which was how he first came to the attention of Chicago detectives and Al Capone, Bugs Moran and Roger Touhy, working "side deal" with each of them.

     All of them considered Winkler to be gutless to pull off the crimes he planned. "No man in Chicago history ever played both ends against the middle so adroitly."

     Most cops and criminals in Chicago agreed that Winkler and Burke were probably two of the shooters in the St. Valentine's Day massacre. Oddly enough, Winkler, who liked the cops (and the cops were amused by him) once told a detective that he often envisioned his own death by "lots of bullets, from out of nowhere."

     In 1932, Winkler turned over bonds to the so-called Secret Six, the committee looking into means to bust the Capone mob. The bonds came from a Lincoln, Nebraska robbery Winkler had played a part in, but when the cops started to close in, Winkler cut a deal with the Secret Six, ratted on the others, and walked away safely.

     That same year, Winkler took Teddy Newberry's place in the Northside gangs as an underworld financial backer, and a provider of shelter and equipment to gangsters on the run...for a very healthy sum, of course. He even moved into Newberry's old apartment at 3300 Lake Shore Drive. Teddy wouldn't be needing it. They found him face down in a pool of frozen water alongside a farm road in Indiana. He had been tied with wire and shot through the eyes.

     Winkler was an egomaniac who talked insistently. Once during a poker game he bragged to Lewis and Marovitz: "You know, I'm the toughest guy in Chicago ... maybe the toughest guy in the whole country."

     Without looking up from his cards Marovitz threw a right cross onto Winkler's chin and knocked him out of his chair.

     "Why'd you do that?" Winkler asked. "To show you that you're not the toughest guy in this room."

     In the last part of his short life, Winkler tried to make himself more refined and started to wear glasses to cover up his crooked, glass eye and even married a tall, gorgeous blonde.

     Winkler and his wife, mother he called her, had one of the strangest relationships in gangdom. She reviewed each and ever illegal endeavor her husband became involved with, first chastising him about the heavenly and earthly illegalities of his work, and then for possible slip-ups in the plan. "Sure mother," Winkler would say.

     Gifted with an eagle's eye for detail, she would review the plan over and over again, looking for potential problems before giving her approval. "She's the best I've ever seen," Winkler boasted.

     According to Joe E. Lewis, in late 1932, Winkler had his eye shot out during the mail robbery, but had made off successfully with the loot anyway, and he was convinced that the Touhy's, his partners in the crime, were out to kill him because he had "not apportioned the loot equitably."

     The day before he was killed, Winkler went to the Mayo Clinic in Minnesota with his lawyer Joe Marovitz and Joe E. Lewis to let the doctors have a look at Lewis's recently slashed throat.

     When they returned to Chicago, Winkler refused to leave his lawyer's side. "I can't go back to my hotel and I'm afraid to register for a new one. Got any idea where I can go?" he asked Lewis who gave him the extra key to his suite at the Seneca Hotel.

     The next day he was gunned down.

     Winkler's killer had waited an hour and a half for him outside the beer plant, owned by Cook County Commissioner Charles Weber, at 1414 Roscoe Street. As Winkler strolled towards Weber's office, the killers leaped out of a green truck and fired low, into his waist. In all, 72 pellets and bullets went into Winkler in a matter of seconds, he was literally riddled with pellets from his neck to his ankles with most of them going into his back, yet not one bullet hit his head or face.

     "Turn me over, I can't breathe," he said, and asked for a priest before he died. Doctors found half-a-dozen religious relics pinned to his underwear; he was a big donor to Father Coughlin who sent him the medals. Winkler died begging for God's mercy on his soul, saying the Lord's Prayer to father James Fitzgerald.

     The Touhy's were highly suspected of ordering the killing although hood-for-hire, Dominic Marzano, was held in questioning for Winkler's killing as was Martin Guifolye and Babe Baron, who would later become a Las Vegas "Big Shot."

     It was never clearly established why Winkler was killed or who killed him. It could have been anyone, for any one of a hundred reasons. But his death was another nail in the coffin of the independent operator. The days of the lone gangster were drawing to a close.

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