Feb. 14, 2022

The St. Valentine's Day Massacre

The St. Valentine's Day Massacre

February 14, 1929. Several members of Chicago’s North Side Gang are murdered in what will come to be known as the St. Valentine’s Day Massacre.

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Cold Open

It’s February 14th, 1929.

On a bitterly cold winter’s morning in Chicago, a group of six men wearing pinstripe suits and fedoras have gathered inside a garage on the north side of town. A seventh man – a mechanic – lies on his back beneath the chassis of a truck.

These men are all members or associates of a criminal organization called the North Side Gang. They use this garage as a safehouse to receive shipments of bootlegged whiskey, smuggled down from Canada.

One of these men is a young mobster named Frank Gusenberg.

Frank checks his watch. Today's shipment is almost twenty minutes late. Impatient, Frank taps the concrete floor with the polished toe of his wingtip.

Prohibition went into effect nine years ago. The constitutional ban on alcohol made it illegal to sell, manufacture or transport booze. But it said nothing about drinking it. And after prohibition went into effect, Americans still craved their alcohol; they just needed to find a way to get their hands on the stuff. The sudden demand for illegal alcohol led to the proliferation of organized crime here in Chicago and across the country.

With multiple groups vying for control of Chicago’s lucrative bootlegging operations, fierce competition quickly emerged. The biggest rivalry is between the North Side Gang and the Chicago Outfit – an organized crime syndicate run by a notorious gangster named Al Capone.

Frank Gusenberg is no fan of Capone, and neither are his fellow gang members. If given the chance, Frank would gladly put a bullet between Capone’s eyes. But today, Frank isn’t worried about Capone. Instead, he's focused on the task at hand: picking up this shipment of whiskey.

Then finally, at 10:50 AM… 

The garage doors open and four men walk inside, dusting snow from the shoulders of their jackets.

It takes Frank a moment to realize that two of the men wear police uniforms. One of them calls out, “this is a shake-up.” And before the gangsters can make a run for it, the cops open their jackets to reveal sub-machine guns and point them directly at Frank and his associates.

The cops tell Frank and the other men to stand facing against the wall. They do as they’re told – but Frank knows something’s not right with these officers. Cops carry sidearms, not machine guns. Every bone in Frank’s body is telling him to run. But instead, he decides to try and reason with these men, whoever they are.

But just as Frank clears his throat to speak... 

Bullets tear through fabric and flesh and ricochet off the brick walls.

All seven men fall to the floor in a haze of dust and gun smoke. By the time the air has cleared, the assailants have vanished, and Frank’s six companions, including his older brother, Peter, are dead.

The St. Valentine’s Day Massacre – as this bloody event will come to be known – will have far-reaching and unexpected consequences, setting in motion a chain of events that will lead to the end of the Prohibition Era; and it will be the beginning of the end for organized crime kingpin Al Capone, the man who many believe orchestrated this brutal killing that took place on February 14th, 1929.


From Noiser and Airship, I’m Lindsay Graham and this is History Daily.

History is made every day. On this podcast—every day—we tell the true stories of the people and events that shaped our world.

Today is February 14th: The St. Valentine’s Day Massacre.

Act One: The Beer Wars

It’s December 1919, a decade before the St. Valentine’s Day Massacre.

A young Italian-American bouncer stands in the snow outside the Four Deuces – a casino and brothel in Chicago. The young bouncer watches gloomily as pedestrians hurry past, their heads lowered against the biting cold.

Alphonse Gabriele Capone arrived in Chicago from New York a few weeks ago, having been offered this job at the Four Deuces by an old acquaintance from back East, a man named Johnny Torrio. Torrio is the boss of the Chicago Outfit: an organized crime syndicate that operates brothels around Chicago’s South Side. And soon, Torrio will recognize the potential of his young bouncer, and he’ll take "Big Al" Capone under his wing as a protégé.

But in December 1919, Al Capone is only a lowly bouncer, earning a small cut from Torrio’s gambling and prostitution rackets. But changes are coming to America, and no one will benefit more than “Big Al” Capone.

Just a few weeks later, on January 17th, 1920, Congress passes the Volstead Act, a bill designed to enforce the 18th Amendment, which bans the sale, manufacture, and transportation of alcohol.

At the stroke of midnight on January 17th, America’s taps are turned off, and a huge black market for bootlegged booze is created overnight. Among the first to capitalize on this opportunity are organized crime groups, like the Chicago Outfit. With Torrio as boss and Al Capone as his newly-promoted right-hand man, the Chicago Outfit quickly becomes one of the Windy City’s largest bootlegging operations, catering to the city’s speakeasies and other establishments where customers can buy illegal booze.

But the Outfit doesn’t have the market cornered. Other gangs are running similar schemes. The Chicago Outfit’s main competition is a predominantly Irish group, called the North Side Gang, run by a wise-cracking mobster named Dion O’Banion.

In 1921, Torrio meets with O’Banion to negotiate a territorial agreement, hoping to avoid bloodshed over turf disputes. The two leaders agree that the North Side Gang will stick to the North side, while the Chicago Outfit will stay in the South. And for a time, this truce holds, with both gangs refraining from infringing on each other’s territory.

But the peace doesn't last forever.


In September 1924, O’Banion hears that police are planning to raid his biggest brewery. Rather than cutting his losses, O’Banion spies an opportunity to double-cross his Italian rivals. He sells the brewery to Torrio and Capone for $500,000 - a huge sum but small change for a Chicago kingpin. When Torrio arrives to take possession of the brewery, the police descend and place him under arrest.

When Capone learns of O’Banion’s betrayal, he vows to exact revenge. 

On November 11th, 1924, at the flower shop that serves as a front for his less wholesome endeavors, O’Banion is working quietly, when two gunmen enter the store and shoot the Irishman dead. Al Capone denies any involvement, but the slaying of Dion O’Banion plunges the Windy City into a period of gang violence known as “the Beer Wars” – a struggle for supremacy between Chicago’s bootleg mobs.

Following O’Banion’s murder, the North Side Gang demand reprisals. On January 24th, 1925, while awaiting trial for the brewery sting, Johnny Torrio is nearly torn apart by a .12 gauge shotgun. As Torrio bleeds out on the ground, the getaway car speeds off in a cloud of exhaust. Behind the wheel is mobster Bugs Moran, and holding the smoking shotgun is Hymie Weiss, the new leader of the North Side Gang.

Miraculously, Johnny Torrio survives his injuries, but the experience convinces him to step down as the boss of the Chicago Outfit. Torrio returns to New York, leaving the Outfit in the hands of Al Capone.


Suddenly in charge, Big Al cements his reputation as Chicago’s premier kingpin. By 1926, the annual income from Capone’s bootlegging operation is over $100 million, over one and a half billion today. Capone uses his extravagant wealth to indulge in a celebrity lifestyle, driving around Chicago in his seven-tonne bullet-proof Cadillac, and hosting lavish parties.

But as his fame increases, so do his expenses. Capone shells out $30 million a year bribing the police to turn a blind eye to his criminal activities.

And meanwhile, the Beer Wars rage on.

Nearly every morning, Chicago’s newspapers are filled with grizzly reports of gangland violence. Speeding cars with Tommy guns flashing in the windows are regular sights along Michigan Avenue. And by 1926, over 300 mobsters have been murdered in Chicago – many of them at the behest of Al Capone.

In October of that year, Capone’s goons take out Hymie Weiss, leaving Bugs Moran in charge of the North Side Gang. Bugs is now the only thing standing between Capone and uncontested control of Chicago’s criminal underworld.

But in January 1929, members of Bugs’ North Side Gang strike back killing one of Capone’s close associates. In response, Capone decides to send Bugs a love letter in the form of a mass assassination to be carried out on Valentine’s Day. Capone’s plot will succeed in destroying the North Side Gang, but it will also spark a series of events that will lead to Al Capone’s downfall.

Act Two: Public Enemy No. 1

It’s February 14th, 1929, in Chicago.

Today is Valentine’s Day, and as the city’s bakers and florists prepare for the holiday rush, police sergeant Thomas J. Loftus speeds down Clark Street, responding to a report of shots fired.

Just as he pulls up outside the SMC Cartage Company, a black Cadillac slowly rounds the corner and disappears from view. But Sergeant Loftus doesn’t see it. He jumps from his car and races inside the garage, where seven bullet-riddled bodies lie slumped on the cold concrete, dimly lit by a single flickering light bulb.

Almost immediately, Sergeant Loftus notes that the dead men are members of the North Side Gang. He recognizes most of the goons from police line-ups. Lying in their own blood is James Clark, an armed robber; Frank Snyder, an accountant who cooks the books for Bugs Moran; and the Gusenberg brothers, Frank and Peter, two of Chicago’s most notorious thugs.

But then the Sergeant hears a sputtering sound and realizes that Frank is still breathing. He kneels by his side and asks “Do you know me, Frank?” Frank grimaces, his teeth glossy and dark with blood. “Sure,” he replies. “You’re Tom Loftus.” Sergeant Loftus demands to know who shot him. But even while dying, Frank sticks to the gangster’s code of silence. “No one,” says Frank. “No one shot me.”

Shortly after that, Frank succumbs to his gunshot wounds.

The following morning, newspapers across America are splashed with gruesome photographs of the crime scene. Never before have such graphically violent images appeared in the press. And a public outcry ensues, mounting pressure on the federal government to do something about the organized crime epidemic – and the Prohibition laws that seem to be the cause of it.


In Chicago, U.S. attorney George E. Q. Johnson is given the task of catching those responsible for the St. Valentine’s Day Massacre. Straight away, Al Capone is assumed to be connected to the shooting, since the victims were all associated with his rival gang.

But there’s a problem with the theory. Capone has a watertight alibi. He was in Florida at the time of the shooting, vacationing at his mansion in Miami Beach. When asked by reporters to comment on the Massacre, Capone feigns shock. And although investigators believe Capone to be guilty, they simply cannot find any hard evidence linking him to the crime.

So with Capone apparently out of the frame, investigators consider the testimony of a slew of witnesses. Several passers-by reported seeing police officers driving away from the crime scene in a black Cadillac. Police corruption is rampant in 1920s Chicago, and it’s not inconceivable that a few rogue officers were caught up in a gangland dispute. But nothing comes from this line of inquiry, and eventually, that theory is dismissed.

For U.S. attorney George E. Q. Johnson, the trail is quickly running cold.

But then, less than a month after the Massacre, a new President arrives at the White House and brings with him a determination to eliminate the scourge of organized crime.


It’s March 1929. 

Newly inaugurated President Herbert Hoover meets with members of the Chicago Crime Commission. This Commission’s delegates share their concerns with President Hoover about recent gang violence in Chicago. Of particular concern is a man whom they refer to as “Public Enemy No. 1”: Al Capone.

Hoover listens intently, his expression grave. Following the meeting, he instructs all federal agencies to concentrate their efforts on “getting” Capone. A federal task force is formed – not of FBI enforcers, but of US Treasury agents. Rather than digging into Capone’s violent criminal past, these agents are going to look at his tax returns. If they can’t arrest Capone for orchestrating the Massacre, maybe they can get him for cheating on his taxes.

In the meantime, a specialist unit of the Federal Bureau of Prohibition, headed by agent Elliot Ness, begins assembling a massive charge sheet based on Capone’s bootlegging operations. Capone repeatedly tries to bribe Ness and his agents but to no avail, earning Ness’ squad the nickname: “the Untouchables.”

In June 1931, following the efforts of both the Untouchables and the US Treasury taskforce, Capone is arrested and charged with 22 counts of federal income tax evasion, and 5,000 counts of violating Prohibition laws. Just two years after the St. Valentine’s Day Massacre, Al Capone pleads guilty and is sentenced to eleven years in Alcatraz.

But even with Capone behind bars, the St. Valentine’s Day Massacre will continue to resonate through the halls of power in Washington, as many in the US government are forced to consider the possibility that the real culprit for the widespread violence isn’t Al Capone or any other mobster; but rather the 18th Amendment.

Act Three: Party’s Over

It’s January 7th, 1931, two years after the St. Valentine’s Day Massacre.

Republican President Herbert Hoover sits behind his desk in the Oval Office reading an important report.

During the presidential election of 1928, then-candidate Hoover endorsed Prohibition. But he also promised that, if elected, he would appoint a commission to study the efficacy of the constitutional ban on alcohol. Not long after winning the White House, Hoover made good on that promise.

Spurred on by the bloody St. Valentine’s Day Massacre, Hoover established the National Commission on Law Observance and Enforcement, informally known as the Wickersham Committee. The purpose of this committee was to study the effectiveness of Prohibition, and its impact on organized crime. Today, the committee has published its findings. As Hoover reads the lengthy report, a frown creeps across his face.

Report’s analysis is clear: many Americans are tired of Prohibition because it simply does not work. In spite of the heroic efforts of law enforcement, organized crime persists and even thrives; as does the violence associated with the bootlegging industry.

Still, in spite of their findings, 10 of the 11 commission members are opposed to the repeal of the 18th amendment. Hoover too maintains his stance, even in the face of mounting political opposition.

And when the Wickersham Committee’s findings are reported in the national press, public support for Prohibition plummets to an all-time low. Clamors to repeal the 18th amendment are further fueled by economic hardship, as America struggles with the consequences of the Great Depression. Many in Washington come to believe that legalizing the liquor industry will create jobs and increase tax revenue.

But Hoover isn't swayed by public opinion or these political realities. Instead, he focuses on increasing federal efforts to enforce the 18th amendment. And this proves to be a costly miscalculation.

The 1932 presidential election is largely a referendum on Hoover’s response to the Great Depression. And Prohibition is a wedge issue of great significance for many American voters.

In the summer of 1932, Hoover’s opponent, New York Governor Franklin Delano Roosevelt, takes the stage at the Democratic National Convention in Chicago. There, he tells his fellow party members speaking about the 18th amendment that “This convention wants repeal. Your candidate wants repeal. And I am confident that the United States of America wants repeal.” Roosevelt’s firm stance against Prohibition helps him beat Hoover in a landslide on election day.

And Roosevelt’s victory all but assures that in February of 1933, Congress will pass the 21st amendment, which states: “the eighteenth amendment to the Constitution of the United States is hereby repealed.”

The 21st amendment will be ratified before the year is out, officially bringing a conclusion to the so-called ‘noble experiment’ of prohibition. After 13 long years, the age of gangsters, speakeasies, and bootlegging comes to an end, in part, as a result of the gangland violence that occurred in a cold Chicago garage on February 14th, 1929.


Next on History Daily. February 15th, 1898. An explosion in Havana harbor sinks the USS Maine battleship, killing hundreds of American seamen and precipitating the Spanish-American War

From Noiser and Airship, this is History Daily, hosted, edited, and executive produced by me, Lindsay Graham.

Audio editing by Mollie Baack.

Sound design by Mischa Stanton.

Music by Lindsay Graham.

This episode is written and researched by Joe Viner.

Executive Producers are Steven Walters for Airship, and Pascal Hughes for Noiser.