No love lost: remembering the bloody Valentine’s Day Massacre

No love lost: The bloody Valentine’s Day Massacre that cemented Al Capone’s reign over Chicago when seven of his rivals were executed in a hail of 100 bullets by men dressed as policemen in a gangland murder that technically remains unsolved, 90 years on

  • WARNING: GRAPHIC IMAGES: Al Capone is widely believed to have orchestrated the ‘Valentine’s Day Massacre’ in which 7 members from the rival North Side Gang were executed against a wall by men dressed as police
  • Capone and his adversary Bugs Moran turned the streets of Chicago into a bloody battlefield as they fought for territory and control of the lucrative bootlegging industry during Prohibition; a business that escalated the mob  
  • The massacre was a carefully orchestrated plot to off Bugs Moran that involved police disguises and bogus patrol cars; Moran cheated his own death by running late the morning of the massacre 
  • The crime went unsolved because authorities weren’t able to officially connect Capone with any substantial evidence; the case remains unsolved to this day
  • Capone was eventually arrested for tax evasion in 1931; he was paroled after seven years and died from cardiac arrest in 1947
  • At the time of his death, Capone was said to have the mental faculties of a 12-year-old; caused by syphilis that he contracted from one of his brothels 

Organized crime ruled the streets of Chicago during the 1920s as two dueling mob bosses fought to control the city’s illegal gambling, prostitution and bootlegging industries. The Midwestern metropolis descended into lawlessness as politicians and law enforcement were bribed into silence while the mafia waged bloody warfare across the city.

Trafficking alcohol during Prohibition was a lucrative business for organized crime and Bugs Moran, head of The North Side Gang controlled the majority of shutdown breweries and distilleries that lined the north side of the city. Moran’s monopoly on black market alcohol didn’t sit well with his rival: bootlegging Al ‘Scarface’ Capone, head honcho of the infamous Chicago Outfit.

In 1922, a tempest of violence broke out between the Irish and Italian gangs. The Chicago Sun-Times called it ‘the bootleg battle of the Marne’ as mafia killings and shootouts shook the city. Between 1922 and 1926, 474 mobsters were killed. These years were defined by fraud, revenge murders, bombings, heists and turf wars; punctuated briefly by an armistice between the two enemy syndicates. Capone narrowly escaped death twice in 1925 and 1926 after being ambushed by North Side capos; causing him to drive around in his famous armored vehicle—a three-and-a-half ton fortress on wheels made by Cadillac.

Seven members of Bugs Moran’s North Side Gang were ruthlessly executed against a wall on February 14, 1929 by four of Capone’s henchmen from The Chicago Outfit. The assassins, disguised as police officers released a stream of 160 bullets on their victims with Thompson sub-machine guns. Making it the worst mob hit ever seen in the United States and going down in history as The Valentine’s Day Massacre

Disputes over the Chicago’s bootlegging industry reached fever pitch in 1929 after Al ‘Scarface’ Capone orchestrated a hit on seven members from Bugs Moran’s North Side Gang. Moran was the intended victim of the massacre but cheated death by mere minutes because he was running late that morning

Al ‘Scarface’ Capone (pictured left) was the cold-hearted commander of ‘ The Chicago Outfit.’ His long standing beef with George ‘Bugs’ Moran (pictured right) turned Chicago into a bloody battle field as they fought for control over illicit alcohol trafficking during Prohibition

The conflict came to a climax on February 14, 1929 – history’s biggest single-day mob hit that saw seven members of Bugs Moran’s North Side Gang executed against a wall by four assassins disguised as uniformed policemen wielding machine guns. Photos of the gruesome mass executions were published in newspapers the next day; leaving Americans stunned and speechless over what became known as the St. Valentine’s Day Massacre. This year is its 90th anniversary.

Valentine’s Day, 1929: the North Side Gang was lured to the SMC Cartage Warehouse on 2122 North Clark Street under the false promise of a stolen, cut-rate shipment of Canadian whiskey that belonged to Capone. The Gusenberg brothers (two of the seven victims) arrived at the warehouse with two empty trucks that were intended to drive to Detroit later that day to intercept Capone’s delivery.

A special crime committee is sworn in over the bodies of the victims of the Valentine’s Day Massacre on February 15, 1929. Capone was immediately suspected of coordinating the savage crime but was never formally charged because of his airtight alibi– he was at his vacation home in Miami during the time of the murders

 To this day, the Valentines Day Massacre has never been solved despite circumstantial evidence incriminating Capone in the crime

Peter (left) and Frank (right) Gusenberg two of the victims were two of the seven victims.  Both brothers were contact killers for The North Side Gang. Frank survived the massacre despite being shot 14 times but refused to break the Mafia vow of silence in identifying his attackers. He died at a local hospital three hours later

The hit was intended for Bugs Moran and his top lieutenants but instead Moran was running late that morning and missed the massacre entirely by a few minutes. It was 10.30 AM and he left his Parkway Hotel apartment toward the warehouse where his men were already waiting. As he approached the building, he noticed a patrol car prowling the area and decided to turn around and bide his time at a nearby coffee shop. A decision that saved his life.

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Within minutes, two of henchmen emerged from a Cadillac sedan that blocked the rear entrance of the building while another two dressed as fake police officers emerged from the same ‘patrol car’ Moran spotted moments earlier. The uniformed men approached Moran’s gang and ordered them to line up against the wall; thinking they were under arrest, the seven gangsters complied.

Keeping up with Capone: The man behind The Chicago Outfit

Mugshot taken November 1930

Al ‘Scarface’ Capone was born Alphonse Gabriel Capone in 1899 to Sicilian immigrants who settled in Brooklyn, New York. 

Scrappy and bawdy, the young Capone earned his infamous moniker from the deep lacerations he sustained during a knife fight with Frankie Gallucio at a Coney Island dance hall. He cut his teeth in local New York City street gangs as a teenager before moving west to The Windy City aged 20. 

His closest friends called him ‘Snorky’—a term for a sharp dresser. Capone indulged in his expensive taste for bespoke suits, flashy jewelry, food, cigars and liquor. His drink of choice was Templeton Rye from Iowa and his weakness was women. 

At the height of his career, Capone ran roughly 6,000 speakeasies and made over $100 million per year. (Roughly $1.3 billion in today’s money). 

Prohibition provided a lucrative business opportunity for organized crime; whose principal dealings in petty theft, gambling and racketeering amounted to trivial sums of money before the 18th Amendment prohibiting was ratified in 1920.

The dispatchers then opened fire with Thompson sub-machine guns, systematically spraying their victims from left to right and continuing to shoot after all seven had hit the floor. Two additional shotgun blasts all but obliterated the faces of John May and Albert Kachellek, according to the coroner’s report. The other victims were: Adam Heyer, Reinhardt Schwimmer, Albert Weinshank, and the Gusenberg brothers, Peter and Frank.

The crime wasn’t reported until a neighbor walked over to the garage and pushed open the door to find the disfigured bodies in pools of blood, gun smoke still lingered in the air. Eye witnesses saw two ‘police officers’ leaving the garage while prodding their plain clothed associates into a ‘police car’ that speedily took off down the street. It was all part of the bogus scheme.

Responding authorities arrived on the scene to find Frank Gusenberg miraculously still alive despite having been shot 14 times. When questioned by the police, he said ‘No one… nobody shot me.’ He died three hours later at a local hospital, observing the gangster code of ethics and silence known as omerta. His final words were, ‘I ain’t no copper.’

The massacre effectively put an end to the tit for tat warfare that waged across Chicago. Capone was instantly suspected in orchestrating the crimes but was never charged since he had a water tight alibi: he was across the country at his home in Miami at the time. Moran broke mafia code and famously told reporters: ‘Only Capone kills like that.’ When reached for comment, Capone responded: ‘The only man that kills like that is Bugs Moran.’

The Chicago Outfit immediately began tying up loose ends by destroying evidence that traced them back to the crime. On Feb 22, 1929, police were called to a garage fire on Wood Street where a 1927 Cadillac sedan was found disassembled and set ablaze. It was determined to be the same car used by the assassins during the massacre a week earlier. Police then announced that Capone allies, John Scalise and Albert Anselmi were suspects in the Valentine’s Day killings but they were mysteriously murdered before ever being formally questioned by the police.

Bugs Moran managed to keep control of his territory through the end of Prohibition in 1933, but the North Side Gang never fully recovered from what is widely recognized as Capone’s decisive blow. Eventually the Irish mafia kingpin was arrested for an unrelated robbery charge and died in prison at age 63 in 1957. 

  • 85 years since Prohibition ended: Gin gushed and beer flowed…

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The Valentine’s Day slaughters haunted and shocked Americans as the lurid details quickly spread across the country. The crime went unsolved as authorities weren’t able to officially connect Capone with any substantial evidence, he became known in the newspapers as ‘Public Enemy Number 1.’ This led President Herbert Hoover to command an official order to the FBI: simply ‘get’ Capone.

Al Capone’s bullet proof and bombproof Cadillac photographed in 1933. The V8 engine could whip the 3.5 ton car into top speed at 110 mph; making it the perfect getaway vehicle. In 2012, the car was sold at auction for $341,000

The S-M-C Cartage Company warehouse at 2122 North Clark St. in Chicago was the site of the infamous St. Valentine’s Day Massacre

The massacre set off public outcry for Chicago law enforcement to clean up the city’s organized crime that skyrocketed during the 1920s under Prohibition. National support for the 18th Amendment began to wane which posed a big problem for gangsters and the federal government. The FBI ruthlessly shook down mob bosses in an effort to quell gang activity and restore justice. Shortly after the savage slaughters, The New York Times reported, ‘Tonight an underworld round-up unparalleled in the annals of the Police Department is under way.’ The article went on to quote Chicago’s Police Commissioner William Russell, ‘It’s a war to finish. I’ve never known of a challenge like this – the killers posing as policemen – but now the challenge has been made, its accepted. We’re going to make this the knell of gangdom in Chicago.’

Finally, the notorious gangster’s crimes caught up to him and in 1931, he was convicted of federal income tax evasion and sentenced to 11 years behind bars. The larger-than-life mob boss was in poor health when he arrived at Atlanta U.S. Penitentiary. Capone had contracted syphilis at an early age from one his brothels and it began to take a heavy toll on his mental faculties. He was also diagnosed with gonorrhea and suffering withdrawal symptoms from a cocaine addiction that perforated his nasal septum. Capone was released on parole after seven years and died of cardiac arrest in his Palm Island, Florida home on January 21, 1947.

To this day, The Valentine’s Day Massacre remains unsolved.

 Chicago Daily News front page reporting the St Valentines Day Massacre in 1929

Capone eluded incrimination by destroying evidence. On Feb 22, 1929, police were called to a garage fire on Wood Street where a 1927 Cadillac sedan was found disassembled and set ablaze. It was determined to be the same car used by the assassins during the massacre a week earlier


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