Secrets Behind The St. Valentine’s Day Massacre

On the morning of February 14, 1929, Chicago was locked in ice.

Snow lay in filthy gray drifts along Clark Street on the city’s North Side. Inside a brick garage at 2122 North Clark Street, seven men waited in the cold, believing they were about to make the biggest liquor deal of their lives.

Instead, they were about to be executed.

Chicago in the late 1920s was not ruled by law. It was ruled by bootleggers.

Prohibition had turned alcohol into gold and Chicago into a battlefield. Two men stood above all others.

On the South Side was Alphonse “Al” Capone, a brilliant, ruthless empire builder whose breweries, distilleries, and speakeasies stretched across the city.

On the North Side was George “Bugs” Moran, the last major boss standing in Capone’s way.

Their rivalry was not just about booze—it was about control of Chicago itself.

By early 1929, Capone had grown tired of the constant ambushes and assassinations between his gang and Moran’s. The North Side Gang had already tried to kill Capone twice. If Moran lived, the war would never end.

So Capone’s lieutenants devised a plan to end it in a single morning.

They spread word that a massive shipment of hijacked Canadian whiskey was available at a discount. The pickup would happen at the North Clark Street garage—a warehouse used by Moran’s men to store liquor.

The bait worked.

Shortly before 10:30 a.m., Moran’s crew began arriving.

Inside the garage were seven men:

• Frank and Peter Gusenberg, Moran’s top enforcers
• James Clark, Moran’s brother-in-law
• Adam Heyer, the gang’s bookkeeper
• Albert Weinshank, a Moran associate
• John May, a mechanic who was only there to fix a truck
• Reinhardt Schwimmer, a doctor who liked to follow gangsters for thrills

They thought they were waiting for whiskey.

Outside, a lookout spotted what he believed was Bugs Moran approaching the garage. In reality, Moran had paused across the street to light a cigar—a delay that saved his life.

Seeing police uniforms approaching, Moran turned and walked away, believing a routine raid was underway.

At 10:30 a.m., a stolen police car pulled up to the garage.

Four men got out.

Two wore Chicago police uniforms.

Two wore trench coats.

The men inside the garage saw the uniforms and did not reach for their guns.

They lined up against the wall, just as they had done dozens of times before during police raids.

The fake officers pretended to disarm them.

Then the trench-coated men stepped forward and raised two Thompson submachine guns.

The garage exploded in sound.

More than 70 rounds were fired in seconds.

Bullets ripped through flesh, bone, and concrete. Men screamed, fell, and twitched on the bloody floor. The Gusenberg brothers were hit over a dozen times each.

One of them, Frank Gusenberg, was still alive when real police arrived.

When asked who shot him, he whispered:

“Nobody… shot me.”

It was the gangster’s code—even in death, you do not talk.

The killers left the scene in a final act of genius.

The two fake cops marched the two trench-coated gunmen out at gunpoint, making it look like a police arrest. Witnesses thought the killers had been caught.

They vanished into Chicago.

When police entered the garage, they found seven bodies stacked against a brick wall, riddled with bullets.

The North Side Gang was shattered.

And yet the most important man of all was missing.

Bugs Moran was alive.

Al Capone was never charged. He was in Florida at the time, carefully establishing an alibi.

Everyone knew who had ordered the massacre.

But no one could prove it.

The outrage from the murders was so intense that it finally turned public opinion against the gangsters. The government could not convict Capone for murder—but they would get him for something else.

In 1931, Al Capone went to prison for tax evasion.

The St. Valentine’s Day Massacre did not end organized crime.

But it ended the illusion that gangsters were glamorous.

Seven men had been lined up like cattle and slaughtered in a garage.

And Chicago—and America—would never forget it.

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