August H. "Gus" Winkler — the family name apparently was originally spelled with an extra E, as Winkeler — was always a bit of an outsider after he moved to Chicago and became one of Al Capone's "American Boys."

"The American Boys" was Capone's designation for a crew he used for special assignments, such as the St. Valentine's Day Massacre. Winkler and Fred "Killer" Burke were perhaps the best known; others included Bob Carey, Fred Goetz and Raymond "Crane Neck" Nugent.

They were not well-liked by other Capone associates, particularly Frank Nitti, who would take over the Chicago mob after Capone was convicted of income tax evasion in 1931.

Winkler was the least-trusted of "The American Boys" because he talked too much. Apparently he had no secrets from his wife, Georgette, who was five years older than he was, and would write a memoir about their life together, including everything he had told her about his career as a gangster.

Of course, when Capone went off to prison, neither he nor Nitti nor anyone else in the mob was concerned about Winkler's conversations with his wife. What began to bother Nitti were the conversations Winkler was having with police and federal authorities.

In early October, 1933, Winkler was spotted at the Bankers Building, the Chicago office of the FBI and special agent Melvin Purvis.

That was the last straw.

Buffalo Courier-Express, October 10, 1933
CHICAGO, Illinois, October 9 (AP) — Gus Winkler, affluent and sinister power in the world of gangsters, was assassinated today as his hand turned the doorknob of a beer distributing depot.

Three killers motored down a north side street in an old green truck as Winkler strolled up to the door.

The truck slowed down. Guns were poked out, and a blast of buckshot poured into Winkler’s back. He fell, and the shotguns roared again. Sixty-five wounds had been torn into his body.

He lived just 40 more minutes.

“YOU'RE DYING," the police whispered to him at John B. Murphy Hospital. “Who shot you?”

Winkler moaned for water, for a clergyman. but in spite of a rumor he had been slain for betraying some criminal, he said not word about his killers.

Winkler’s assassination followed a series of swift developments in the war against crime by governmental and local officials, centering around the $250,000 post office robbery in Chicago last December. Edgar B. Lebensberger, night club owner and Gold Coast dweller, was found shot to death last Friday.

A few hours after the finding of his body, it became known he had been indicted in connection with the post office robbery. Though a coroner’s jury held he committed suicide, some authorities ventured an opinion the possibility he had been slain.

ONE THEORY, that of Detective Captain Daniel Gilbert, directly linked the deaths of Winkler and Lebensberger.

“Winkler apparently was the contact man between the actual mail robbers and the peddlers of stolen bonds,” said Captain Gilbert. “It is significant that everybody but Winkler was indicted, and it seems obvious that Winkler was a government informer. He was the only man alive, apparently, who could put the finger on the gangsters who robbed the mail messengers.”

Agent and past heir of the Al Capone underworld power, Winkler’s career had flashed into prominence in recent years as a sort of go-between for bank robbers operating throughout the land. Because of that reputation, government agents hunted him down a fortnight ago to be questioned concerned the Urschel kidnapping, the search for George “Machine Gun” Kelly, and the killing of policeman Miles Cunningham by the gunners who had just robbed Federal Reserve Bank messengers of two sacks on a Loop street.

They found him inn a luxurious Lake Shore apartment, living in his tapestried abode as George Michels. They turned him over to the police and a jury acquitted him of a vagrancy charge a week ago. Another warrant was issued and he was out on bond when slain.

LEBENSBERGER was an associate of Winkler and of the slain Ted Newberry, and the circumstances of his death caused police to wonder and look around for Winkler. Then came word of Winkler’s death today.

Captain Thomas J. Callahan of the U. S. Secret Service asserted the belief the killers of policeman Cunningham in the recent Federal Reserve holdup had done away with Winkler to seal his lips.

But Winkler had plenty of other enemies.

One of his friends was Fred “Killer” Burke, now finishing his life in Michigan State Prison for the cold-blooded murder of a St. Joseph (Michigan) traffic patrolman.

Two years ago Winkler, driving, as usual, with a gun and a bottle of whiskey at his side, was accosted by police near St. Joseph. He elected to race. His car overturned and Winkler’s skull was fractured.

He was wearing a spare set of teeth over his own, as disguise, and carried several sets of spectacles. An aviator, Winkler gave his name as Jerry Kral, Chicago pilot, but he was recognized and taken on a tour of places in America where he was wanted for bank robbery, murder, kidnapping.

THE "SECRET SIX,"* and bankers’ associations of Nebraska and Illinois took him over at Chicago when his skull mended.

Winkler frankly admitted he was afraid of a jury in Lincoln, Nebraska, and would rather do what he could to recover the $2,870,000 stolen from the Lincoln National Bank and Trust Company than go out and defend himself.

The “Secret Six” and authorities agreed to let him try. They believed then he was a member of the directorate of the sinister Capone gang, and that he knew who the robbers were.

On January 5, 1932, Winkler stood by his bargain. He delivered to a Chicago bank $583,000 worth of the bonds taken in one of the most amazing bank robberies in history, and gave proof that $2,217,000 of the non-negotiable securities had been burned. All the time he asserted his own innocence of the robbery.

PERHAPS THAT JOB as go-between cost him his life today. It may be the murderers of policeman Cunningham, or members of the mail robbery band the government was relentlessly rounding up today — 24 are held in connection with that crime in several cities — or his confederates in scores of crimes, decided he was safer dead.

The Secret Service was investigating his connection with the Federal Reserve robbery. District Attorney Dwight H. Green and the postal inspector said Winkler had no connection with the quarter million dollar holdup a year ago.

There was no loose work by the executioners today. The ancient green truck moved up precisely at the moment Winkler hoisted a leg over the little iron railing in front of the beer station and tavern owned by Charles H. Weber, a county commissioner and former state legislator. Weber was in Florida today, but associates said Winkler had no interest in the beer depot.

WINKLER'S HAND rested on the doorknob when the shotguns exploded. Only a few slugs spattered against the bricks. No windows were broken. The slugs were well directed.

This time Winkler had no gun, nor could he have used it. He sprawled over the sidewalk in his new blue suit and made no answer to the Weber employees who ran to his aid. In his pocket they found $280 in cash.

The car he had driven to the opposite curb was registered by his bodyguard’s sister. Last April 1, Winkler and the bodyguard, David Goldblatt, had been arrested carrying weapons and several thousand dollars in envelopes, marked as though for payoffs. He was convicted of gun-toting, but appealed.

THERE WAS no talking at the hospital. Police tried to question him, but Winkler paid no heed

“They’ve got me, I know it,” he cried. “Give me a glass of water,” and he asked for a clergyman.

While a priest was murmuring the rites of his church, Winkler died. A few moments later a group of surgeons, attending a convention of the American College of Surgeons here, stepped into the operating room and examined the body of the gangster.

* "The Secret Six" was the name given to a group of Chicago business men, who, in response to grave concern over Al Capone's power and police corruption, had launched their own investigation, hiring Alexander Jamie, a former special agent of the U. S. Department of Justice.

Buffalo Courier-Express, October 11, 1933
CHICAGO, Illinois (AP) — The body of Gus Winkler, gangster overlord, 111 shotgun slugs removed therefrom, was transferred tonight from a stone slab in the morgue to a $10,000 silver coffin, and police announced themselves expectant of further gangster killings.

So fearful were authorities that the Winkler assassination might evolve into a vicious circle of shootings that federal agents profusely armed were assigned to guard witnesses in the $250,000 Chicago mail robbery of a year ago.

Suspicion that the shotgun pellets were sent into Winkler’s back because he had become, or was about to become loquacious with police officials about the robbery was admitted by the investigators concerned.

Forty odd suspects have been arrested about the country for dealing in the bonds stolen in the robbery, a nightclub owner has committed suicide, and police were searching diligently for Winkler when the assassins slew him.

His widow testified at the inquest today that during the height of the search, Winkler had made arrangements for a police escort to take him this morning to the office of United States Attorney Dwight H. Green.

It was Mrs. Winkler, blonde, plump, and named Georgette, who arranged for the ornate coffin. “The best is none too good for Gussie,” she said, adding that his large collection of diamonds would be buried with him.

Three suspects were arrested for the killing today, mainly because they were indiscreet enough to loiter in poolrooms and on street corners near the scene of the shooting at the front door of County Commissioner Charles H. Weber’s beer distributing agency.

All have police records, but police indicated no firm belief they were the actual slayers commissioned by higher-ups in gangdom to dispose of Winkler.

Winkler’s conduct had been exemplary during their twelves years of association, the widow said. He came home every night for dinner at 5 p.m., she said, except when Chief of Detectives William Schoemaker was looking for him.

“He must have gone there to meet someone,” she said when asked why Winkler was entering Weber’s establishment when he was shot.

Police Captain James Fleming also said he believed Winkler had an appointment in the place.

He pointed out that the green paneled truck from which the killers fired had been parked near the beer agency for some time. Police said they believed Winkler was search for bond for one of the suspects held in the mail robbery.

Late in the afternoon police found David Goldblatt, former bodyguard of Winkler, as he walked along a street, and took him to the Town Hall station for questioning.

“Gus telephoned me yesterday morning,” said Goldblatt, “and told me to meet him. I met him at 1 p.m. He was nervous. He said he wanted to borrow my car and added that he was going down to the Federal Building.

Goldblatt said Winkler told him he had “business” to talk over with Mr. Waugh. It was believed he referred to his attorney, William P. Waugh, who later told police he was awaiting Winkler when he received word of the gangster’s death.

Goldblatt denied he had been at the scene of the shooting, and added that he was not an associate of Winkler.

Detective Chief William Schoemaker ordered Goldblatt taken to detective headquarters, where he will be viewed by witnesses of the killing.

Police declared Winkler’s slayers apparently knew of the appointment scheduled with the authority.

Waugh said that while he was waiting for Winkler, someone telephoned him, stating, “Gus won’t be able to keep that appointment. He has had an accident.”

Most of those held were associates of Edgar Lebensberger, cafe owner who shot himself a few hours before an indictment was voted against him. One of them, John J. “Boss” McLaughlin, former state legislator, after hearing of Winkler’s death, decided he would remain in jail and dropped a request for his bond to be reduced 50 percent, to $25,000.

Investigation convinced police that Winkler’s power in the underworld was well-nigh supreme. They said the $2.870,000 Lincoln (Nebraska) bank robbery, from which he returned nearly $600,000 to escape prosecution, was only one of the projects he directed.

Evidence was uncovered that he directed a nationwide syndicate for disposing of stolen securities and that he bossed gambling places in Chicago that netted millions yearly.

The 1930 bank robbery in Lincoln, Nebraska, was never solved, though now it is generally believed to have been the work of Harvey Bailey. At the time, it was considered the biggest bank robbery in United States history, but because the almost all that was taken were securities the Winkler either returned or had destroyed, the robbers probably spent more cash getting to the bank than they took away from it.

Someone who suffered a similar setback was Mrs. Georgette Winkler when she returned to Chicago after attending funeral services for her husband in St. Louis only to discover burglars had visited her apartment and stolen 10 sable furs valued at $3,000. A week later, Gus Winkler's widow attempted suicide, turning on the burners of her gas stove.

She was found by a friend*, who called police. When they arrived, Mrs. Winkler was heard to say, "Gus, I want to die; I want to go with you."

*That friend was Bonnie White, wife of Gun Winkler's one-time partner-in-crime, Fred “Killer” Burke, who was in prison for killing a Michigan policeman. Bonnie Porter had married Burke in 1930, thinking his name was Richard F. White. At the time, Burke was in Missouri, hiding after fleeing Michigan. For more, see Harvey Bailey.

Georgette Winkler, she made no more suicide attempts, but tried to help police find her husband's killers. (Those three men picked up the day after the murder were soon released.)

To help expose the mob, the Winkler widow wrote a book, but publishers wouldn't touch it, which perhaps saved the woman's life. She turned her manuscript over to the FBI, but the agency shelved it. About 70 years later it was discovered by William J. Helmer, who writes about crime and maintains an Al Capone website.

Helmer edited the widow's manuscript and the result was "Al Capone and His American Boys," a book published in 2011. Much of what is believed today about the St. Valentine's Day Massacre comes from that book. Apparently Winkler called his wife, "Mother," and shared most of his ideas with her, including plans for various crimes.

It's strange looking at photos of people from the 1920s and '30s. Winkler was born in 1901, which means he was only 32 when he was gunned down. Photos make him look about ten years older.

Georgette Bence Winkler was listed as 37 years at the time of her husband's death. Again, photos make her seem several years older, and it's my hunch she was. (From the photo on the left, I'd say Helen Mirren could have played her in a movie ... if it were made 20 years ago.) The Winklers were married in 1920 after they met at her parents' boarding house.

According to John William Tuohy in his piece on americanmafia.com, the Winkler marriage was interrupted occasionally during the next six years for arrests and some jail time. In St. Louis, Winkler and "Killer" Burke were part of a gang called Egan's Rats.

Winkler's Wikipedia biography says Winkler next went to Detroit and briefly joined The Purple Gang before he met Al Capone and moved to Chicago.

Which means Winkler moved very quickly once he arrived in the Windy City. It appears gangsters with the right connections could become very rich very quickly. Winkler probably would have remained rich a lot longer if he hadn't talked so much.

His widow overcame her grief and eventually remarried. She was Mrs. Georgette Marsh when she passed away in 1962.

Gus Winkler's murder was never solved.