When Roger Touhy learned that the mob had murdered Anton Cermak, he rented a plane and flew to Indianapolis to meet with the leaders of the Teamsters International Council. Roger wanted to plan their next steps in the war against the syndicate. But the meeting didn't go well. The International was pulling out of the fight. It was, in effect, surrendering to the syndicate. The union's leadership felt that although Touhy had won battles, without Cermak's clout behind him he would never win the war.
Without the Teamsters' financial support, Roger knew that the war was lost. The best thing to do was to hold off the syndicate for as long as he could, make as much money as he could, fold up his operation and leave Chicago forever, perhaps living out his dream to retire to the wilds of Colorado.
He had other reasons to worry, too. United States Postal Inspectors were hot on his trail for the string of mail robberies that he and his gang had pulled off the year before. Although the robberies had gone well, the rumor in the underworld was that Gus Winkler, one of the crooks who helped Touhy cash in the stolen mail loot, was informing on him.
Roger decided to plug the leak on October 9,1934.
'Smiling" Gus Winkler's motto was "Take care of Winkler first." He had spent most of his criminal career doing just that. This was why the Touhys and everyone else connected with the mail robberies wrongly suspected him of being the government's informant in the mail robberies.
Touhy's own spies had reported that Winkler was seen in the FBI's office in the Bankers Building and on the day before they put seventy-two bullets into him he was seen talking with special agent Melvin Purvis on a side street just inside the Loop.
Before Winkler was tied to the case it was widely assumed that Touhy was at odds with him.
Gus Winkler had started out as a member of Eagan's Rats and by age twenty was a safe blower by trade. He did time from 1920-1926, sentenced for assault and wounding with a deadly weapon. He left St. Louis, moved to Chicago and struck up a lifelong friendship with Fred "Killer" Burke, which was how he first came to the attention of Chicago detectives in 1929.
In 1932 Winkler turned over bonds from a Lincoln, Nebraska robbery in which he had played a part to the Secret Six, a group of Chicago business executives who had banded together to take action against the Chicago underworld. When the cops started to close in, Winkler cut a deal and informed on the others so long as he could walk, reasoning that he had always made it clear that he would squeal in order to save himself.
Winkler took Newberry's place in the northside gangs as a chief financial backer and even moved into Newberry's old apartment at 3300 Lake Shore Drive. In an effort to appear more refined in the later days of his life, he started to wear glasses to cover up his crooked glass eye. He even married a tall, beautiful blonde.
The cops Winkler consorted with were amused by him. It was easy to be amused by Gus Winkler; he was good-natured, smart and a smooth talker. On one of his frequent stops by the detective bureau Winkler told them that he often envisioned his own death by bullets. Most of the cops and criminals in Chicago agreed that Winkler was probably one of the shooters in the St. Valentine's Day massacre, after which he went into seclusion in Cicero where he was said to be in semi-retirement, plotting crimes.
He was widely considered to be too cowardly to execute the crimes he planned. "No man in Chicago history ever played both ends against the middle so adroitly," it was said of him. When Newberry was killed he moved into the Northside gang's leadership and offered shelter and equipment to gangsters on the run.
Winkler was an egomaniac who talked incessantly. Once during a poker game he bragged to his lawyer, Joe Marovitz and the nightclub star, Joe E. Lewis, '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 on to 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."
Winkler and his wife, "Mother" (as he called her)
had one of the strangest relationships in gangdom. She reviewed each and every 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 "You're right, it is an un-Christian act. Now that you've got that load off your chest tell us if the plan is alright."
Gifted with an eagle's eye for detail, she would review a 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, Winkler had one eye shot out during a mail robbery and was convinced that the Touhys 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' 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 at 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 toward Weber's office the killers leaped out of a green truck and fired low; in all seventy-two pellets and bullets went into him 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 gasped.
He asked for a priest before he died and doctors found a half 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.
When told that Winkler was dead, a postal inspector threw up his arms and said "Well, this balls up an already balled up case."
The Touhys were suspected of ordering the killing. Hood-for-hire Dominic Marzano was held for questioning and Matt Kolb's old boss, Martin Guifolye, who was now mostly a gambler, was also being sought for questioning. Guifolye called the police and said he was available for questioning at any time. The cops also hauled in Babe Baron, a "0" of Jacob Arvey who was a close friend of international con man John Factor. Baron, a future kingpin for the mob in Las Vegas, was known to have killed Jimmy Walsh in front of Henrici's Restaurant on December 3, 1929. When cops picked him up for questioning in Winkler's death Baron was carrying a pistol in his coat pocket. He was released after several hours. Baron would go on to run one of the city's more successful car dealerships in the 1950s, due in part to a lucrative contract he had to repair city police cars.
Another suspect was Joe Bergi, Winkler's partner in a garage where he fitted cars with bulletproof siding and windows, police lights and sirens that cop cars used in 1933. Baron later took over all the garage businesses.
In September of that year, Bergi was arrested for harboring "Machine Gun" Kelly. Winkler was suspected of having told the police that Bergi was hiding Kelly and provided information about Kelly's role in the Urshel kidnapping case.
As Winkler was a snitch, there were too many suspects for his murder. To this day the crime remains unsolved.
Even with Winkler dead, postal inspectors were able to use the information he provided and move in on the mail robbers. A secret indictment was filed naming Roger Touhy, Gus Schafer and others in his gang as the persons behind the robberies.