Mystery – Saint Valentines Day Massacre

Many of us have heard about the massacre that happened in Chicago in 1929, specifically on Valentine’s Day. But it’s still an unsolved crime as nobody knows for sure who ordered it, nor who had committed it. Here is the historical case of the St. Valentine’s Day Massacre.

Chicago was a hotbed of mafia related crime in 1929. Al Capone was bootlegging stolen whisky from Canada, and the North Side Gang led by George “Bugs” Moran was trying to take over that portion of the criminal underworld.

Because the perpetrators were never fully identified, the suspects and reasons are all hearsay or theorized by investigators. What we know for sure is that at 10:30am on St. Valentine’s Day, Thursday February 14, 1929, seven men were lined up at a garage at 2122 North Clark Street and were executed by four men carrying Thompson submachine guns, and shotguns.

Who were the victims?

Top L – R: Albert Weinshank, John May, James Clark. Bottom L – R: Peter Gusenberg, Frank Gusenberg, Dr. Rheinhart Schwimmer, and Adam Heyer
  • Peter Gusenberg – an enforcer for Bugs Moran
  • Frank Gusenberg – an enforcer for Bugs Moran, brother of Peter
  • Albert Kachellek – aka James Clark, second in command for Bugs Moran
  • Adam Heyer – Bookkeeper and business manager for Bugs Moran
  • Reinhardt Schwimmer – associated with Bugs Moran, gambled on horse racing
  • Albert Weinshank – Managed several cleaning operations for Bugs Moran – He also looked similar to Moran, including his clothes. The massacre started before Bug Moran was there due to the resemblance of Albert to Bugs.
  • John May – Car mechanic for the Moran gang.

There were four men holding guns that day, two were dressed like the victims, normal daily clothes for 1929 including overcoats and hats, and the other two were dressed in police uniforms. Two of the killers used Thompson guns, one with a 20-round box magazine and the other with a 50-round drum. They continued to fire even after all of the victims had hit the floor. Two shotgun blasts all but obliterated the faces of John May and James Clark. Shot 14 times, Frank Gusenberg wasn’t dead. He was taken to the hospital, and when he was stabilized, he told police, “No one shot me.” He died three hours later.

Why was there a massacre?

Bugs Moran

In short, the massacre was an attempt to eliminate Bugs Moran. Bugs was becoming greedy and had been hijacking whisky shipments from Canada as it made its way to Chicago. Bugs Moran had been trying to take over the dog track racing along with several saloons that were run by Capone, insisting they were in his territory.

Most of the men arrived at the garage by 10:30am, however the main man, Bugs Moran was not there. He had left his apartment late, and met another associate, Ted Newberry outside the garage. Seeing the police, they turned around and went to a coffee shop. On their way they warned another member, Henry Gusenberg, and he too turned around. A final gang member, Willie Marks, seeing the police car ducked into a doorway and jotted down the license number before leaving the area.

The killers had expected to kill Moran and two or three of his men, but they were unexpectedly confronted with seven men; they simply decided to kill them all and get out fast.

Here is where it gets complicated; Who were the men with the guns?

  • Al Capone – He wasn’t holding a gun, but it is strongly believed that he ordered the death of Bugs Moran and the massacre itself.
  • George Lewis, Eddie Fletcher, Phil and Harry Keywell – All members of the Purple Gang based in Detroit, associates of Al Capone. They were cleared of the crime, but they and the Purple Gang would be associated with the massacre for years.
  • Fred Burke and James Ray – Bank robbers who were known to wear police uniforms when on a robbery spree.
    • Fred Burke was living in Detroit and his bungalow was raided by police. In that raid they found: $320,000 in bonds stolen from a Wisconsin bank, two Thompson machine guns, pistols, two shotguns and thousands of rounds of ammo. The machine guns were sent to Chicago for the new science of forensic ballistics. Both guns were used in the massacre.
  • Joseph Lolordo – His brother Pasqualino was murdered by the North Side Gang
  • John Scalise, Albert Anselmi, Jack McGurn and Frank Rio – Gunmen and a bodyguard for Al Capone. Both Scalise and Anselmi were murdered by Al Capone in May 1929 when he learned of their plan to kill him.
  • Byron Bolton – was an associate of the St. Louis Egan’s Rats. Also associated with Al Capone. He had also been the associate of Fred Goetz, who was a hitman.
    • Byron Bolton claimed he was a part of the St. Valentine’s Day Massacre along with Fred Goetz, Fred Burke and several others.

How did it all happen? Per Byron Bolton this is what he claims happened on February 14, 1929. Whether it’s true or not will never be known.

Byron Bolton and Jimmy Moran were watching the garage and were to phone the killers at the Circus Cafe when Bugs arrived. Byron claims there were two cars each with a driver, and then the four shooters. Byron named Fred Burke, Fred Goetz, Bob Carey, Raymond Nugent, Claude Maddox, and Gus Winkeler as the men who were in the cars.

Byron’s version of the events was corroborated by Georgette Winkeler, Gus’ widow. She had published her memoirs in 1935-36 and revealed that her husband and his friends had formed a special crew used by Al Capone for high-risk jobs. They were nicknamed the “American Boys”.

Whether the American Boys did the crime or not, it’s still an interesting story and one that leaves people talking and dissecting. The garage was demolished in 1967. The bricks were purchased and displayed in various locations, many have been sold and the rest are owned by the Mob Museum in Las Vegas.

Happy Valentine’s Day

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