Over the last 96 years, the escapades of Al Capone, Chicago's legendary gangster and mob boss, became inescapably entangled with the legends and lore of Route 66. After all, Capone rose to fame – or infamy – during the mid-1920s, and U.S. Highway 66 was born as part of the federal numbered highway system in 1926. But more importantly, Chicago was the designated original eastern terminus (at Jackson Boulevard and South Michigan Avenue) of Route 66, and the City of Chicago was Capone's adopted home city. Sitings of Capone and his associates were commonplace along the length of Illinois' highways, especially between Chicago and St. Louis, during the Prohibition years (1920-1933).
Illegal booze manufactured in carefully-hidden stills ruled the underworld and made deadly enemies of rival gangs. The SMC Cartage Company garage at 2122 Clark Street in Chicago stood three miles north of Route 66, but the horrific event that took place there on Valentine's Day in 1929 became part of the Capone saga, forever tying it to the stories of crime and murder that make up the seamy side of Route 66's legends and lore.
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Capone, born and raised in Brooklyn, came to Chicago in 1920, and found work as a bouncer. It wouldn't take many years before his name was instantly recognized and associated with booze, crime, and violence. “Scarface,” his nickname due to a knife fight's lasting scars on his face, became the most infamous gangster and mob boss in America. It didn't take long after Prohibition began in January 1920 before multiple gangs in Chicago began working the illegal alcohol trade as their primary business.
Turf wars were common between Capone's Italian South Side gang and George “Bugs” Moran's Irish North Side gang. As they remained locked in a gang war for control of the city's bootlegging rackets, shootings were common. But what happened on Valentine's Day in 1929 in Chicago added a sickening dimension to the gangster modus operandi, making headlines around the world, lessening Chicago's tolerance for illegal liquor rackets, and inspiring the FBI to significantly increase their force.
February 14, 1929, dawned cold in Chicago. Several inches of snow clung to the ground from the previous week's precipitation and the below-freezing temperatures. While gentlemen around the city ordered red roses, made restaurant reservations, and addressed valentines to their ladies, seven men – associates or hangers-on of Bugs Moran's outfit – gathered at the SMC Cartage Company garage at 2122 Clark Street. Five of the men were part of the Moran gang – brothers and top enforcers Frank and Peter Gusenberg, retired gang member Albert Kachellek AKA James Clark, bookkeeper Adam Heyer, and business manager Albert Weinshank. Two were not technically part of the gang – mechanic John May and optician-turned-gambler Reinhart Schwimmer who liked to brag that he knew gangsters. The question was why did they gather that morning, and why was Bugs Moran, their boss, not with them, especially since he lived just a block away from the garage at the Parkway Hotel. A falsified liquor delivery may have brought them to the garage as a set-up. And Moran was said to have been headed for the garage himself but saw the police car and ducked into a coffee shop.
About 10:00 am, a black Cadillac touring car, a model often used by police, pulled up in front of SMC Cartage Company. Four men got out, two of them in police uniforms, and went inside the garage. There, no one will ever know what was said, as none of the seven of Moran's men survived the massacre (except for one for a few hours, and he refused to talk), and the four assassins were never convicted and are long dead by now. But from the horrific scene that awaited discovery by neighbors responding to the gunfire and police who arrived soon after, the action that had occurred was clear.
Moran's seven men were lined up facing the brick north wall of the garage and quickly executed by a barrage of 70 rounds of ammunition from two Thompson sub-machine guns, plus several blasts from a twelve-gauge shotgun. Then, the two assassins in police uniforms marched the other two killers out to their police-style automobile to make it look like all was under control as neighbors peered out their windows. Someone called the cops, and a neighbor entered the garage, finding one man, Frank Gusenberg, still barely alive amid the carnage. The other six men were dead, and Gusenberg died several hours later at a hospital. Police and reporters descended upon the gory scene, and newspapers ran shocking photos, showing tangled bodies in pools of blood, with brains and hats sitting next to the men where they fell.
Riveting and enraging the nation's readers, the news also filled the FBI and other law enforcement with renewed vigor. Although Bugs Moran was still alive, his gang was destroyed, and Capone's grip on the illegal liquor business became stronger than ever – for a while. His reign as king of Chicago's booze rackets continued until he was arrested, charged, and sentenced for income tax invasion in 1933.
In an ending to this story that may be disappointing, Capone – nor anyone else – was ever charged and convicted for the Valentine's Day massacre. Capone, as king of organized crime in Chicago, was generally assumed to be responsible. But myriad theories and suspicions surfaced. Could it really have been police or law enforcement, as the two uniformed men and the choice of the vehicle seemed to indicate? Was it Bugs Moran's elimination of troublesome members of his outfit, explaining why Moran himself was not there?
On the day of the massacre, Capone was in Miami, Florida, meeting with Brooklyn District Attorney Louis Goldstein who had come down to Florida to ask Capone questions about another murder, the slaying of New York bootlegger Frankie Yale. After the interview, Capone returned to his winter home on Palm Island – a seemingly airtight alibi on the day of the massacre. But the massacre had turned the tide of public opinion, changing attitudes toward illegal liquor operations and heaping suspicion on Capone as the central figure in Chicago's Beer Wars. To this day, his name is linked to the massacre.
But at the end of the day – St. Valentine's Day, February 14, 1929 – none of the seven men who mysteriously gathered at the SMC Cartage Company that morning, dressed up for a meeting, delivered any valentines or made any romantic gestures that evening. Cheryl Eichar-Jett is the author of numerous books and articles about Route 66. Find her at www.route66chick.com and www.cheryleicharjett.com.
This story originally ran in the February issue of The Prairie Land Buzz Magazine. The Buzz Magazine is distributed free each month to over 400 locations, in 60 cities, in 11 Illinois counties. For more information visit http://www.thebuzzmonthly.com.