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Al Capone was suspected of being the Massacre mastermind but there was no evidence to charge him. Instead, federal authorities built a tax evasion case against him. He was convicted in 1931 and sentenced to 11 years in prison.

Al Capone was in Florida at the time of the St. Valentine’s Day Massacre and claimed he had nothing to do with it. He was never arrested or prosecuted in connection with the crime.

However, Capone did end up going to prison — twice — soon after the Massacre, effectively ending his reign as the leader of Chicago organized crime.

After the Massacre, Capone was summoned to a national Mob conference in Atlantic City, where the leaders determined that Capone needed to lie low for a while. It was arranged for him to be arrested in Philadelphia on a gun possession charge that resulted in a 10-month prison term.

Capone sitting with Fedora
Al Capone was widely assumed to have been behind the Massacre, but he ultimately went to prison for tax evasion. Courtesy of John Binder Collection

Meanwhile, the Treasury Department’s Special Intelligence Unit had targeted Capone. The Intelligence Unit specialized in tax evasion cases, and after several years of relentless sleuthing, it had compiled enough evidence to prosecute Capone.

Elmer Irey
Elmer Irey led the Treasury Department’s Special Intelligence Unit — known as the T-Men — that built the tax evasion case that put Al Capone in prison. Courtesy of Library of Congressy

Convicting him would be a tall order. He was one of the most powerful men in Chicago. He had the police and the politicians in his pocket. And good luck finding hometown witnesses willing to testify against him. But the T-Men had compiled a paper trail that showed Capone reaping big profits without paying his fair share.

Fearing Capone would threaten or kill two key witnesses, agents kept them hidden out of state until it was time for them to testify. And upon learning that Capone planned to tamper with the jury, Judge James Wilkerson introduced a new set of jurors on the trial’s opening day.

On October 17, 1931, the jury found Capone guilty, and he was sentenced to 11 years in prison — one of the most severe tax evasion sentences in history. Capone served most of that time in the island prison of Alcatraz.

Al Capone Mugshot
Al Capone was widely assumed to have been behind the Massacre, but he ultimately went to prison for tax evasion. Courtesy of John Binder Collection

Who Did It

No one was ever prosecuted for the St. Valentine’s Day Massacre, but evidence compiled at the time and revelations in the years since have built a strong argument for closing the book on this case.

So, who did it?

The consensus choice is the “American Boys,” a hoodlum crew out of St. Louis that worked for Al Capone. It was Capone who gave them the nickname, presumably because they weren’t Italians.

A few early clues implicated members of this group.

First, an eyewitness said one of the killers wearing a police uniform had a front tooth missing. Fred “Killer” Burke was missing a front tooth.

Second, a search of Burke’s hideout in rural Michigan turned up two Tommy guns that forensic tests proved were used in the Massacre.

Chicago authorities wanted to prosecute Burke for the Massacre, but Michigan wouldn’t let him go. Instead, he was prosecuted there for murdering a police officer and served the rest of his life in prison.

In November 1931, Cook County Coroner Herman Bundesen officially closed his inquest into the Massacre case, concluding merely that the seven men had been murdered — by someone. But four years later, federal agents arrested a man named Byron Bolton, who surprised investigators by agreeing to tell all about the Massacre.

According to FBI reports, Bolton said the Massacre was planned in late 1928 at a Wisconsin resort owned by Fred Goetz, with Al Capone in attendance. Bolton identified the killers as Fred Goetz, Gus Winkeler, Fred Burke, Raymond “Crane Neck” Nugent and Bob Carey. He said there were two lookouts across the street from the garage: Jimmy “The Swede” Morand and Jimmy McCrussen.

A number of Chicago investigators believed that Bolton’s story checked out, and it was later corroborated by two others: Irene Goetz, who was married to Fred Goetz, and by Georgette Winkeler, who was married to Gus Winkeler. Georgette said the four men who entered the garage and murdered Bugs Moran’s gang were Fred Burke, Fred Goetz, Gus Winkeler and Ray Nugent. She said Burke and Goetz wielded the Tommy guns in the Massacre. The lookouts, she said, were Morand and Bolton, who apparently had modified this part of his story so as to not implicate himself.

FBI Director J. Edgar Hoover did not act on Bolton’s confession, apparently believing the murders were a local police matter.

Although never prosecuted for their roles in the Massacre, most of the American Boys paid for their crooked deeds.

  • Fred Burke was convicted of killing a Michigan police officer in 1931 and spent the rest of his life in prison.

  • Bob Carey was shot to death in 1932 in what authorities declared a murder-suicide.

  • Gus Winkeler was murdered in 1933, allegedly on orders of Chicago Outfit boss Frank Nitti, Capone’s successor, who suspected he was talking to the feds.

  • Fred Goetz was murdered on a street in Cicero, Illinois, in 1934.

  • Raymond “Crane Neck” Nugent was last seen in 1930 with Al Capone in Florida but then he vanished. He is believed to have been murdered.

It’s reasonable to assume the murders of Winkeler and Goetz — and possibly Carey and Nugent — were the result of the Chicago Outfit not wanting to risk the Massacre assailants might talk. But the lack of a spectacular trial to put an exclamation point at the end of the St. Valentine’s Day Massacre story has always marred an otherwise incredible episode in Chicago’s tumultuous organized crime history.

Keep Reading More: The Murder of Jack McGurn

The Murder of Jack McGurn

Jack McGurn, an Al Capone associate who once was a prime suspect in the Massacre, was shot to death in a bowling alley in Chicago..."

The Murder of Jack McGurn - The St. Valentine’s Day Massacre. Feb. 14th, 1929.
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