Chapter 1: What events led to the St. Valentine's Day Massacre?
Imagine it's February 13th, 1929. You're sitting in your office behind a flower shop on the north side of Chicago, bent over a ledger book trying to reconcile the numbers. But the sales you're tallying aren't for roses or carnations. Instead, they're for beer and whiskey. Normally, these are big numbers, but today you're frustrated because they're just not adding up.
You're the leader of one of the largest bootlegging operations in the city. And for the past five years, you've been embroiled in a turf war against a gang based on the South Side, run by Al Capone. One by one, all the other leaders in your organization have been killed or have fled the city. So now it's up to you to stay on top of the books.
You're about to try adding the numbers up again when the phone rings. Yeah, hello? Hey, it's me. You recognize this voice as an acquaintance you've done business with in the past. You narrow your eyes because you've never fully trusted him. Now, what do you want? Why do I have to want something? Maybe I'm just calling to say hello. Are you calling to say hello?
Well, no, but I've got an opportunity for you, and you're not going to want to miss out. All right, what's that? There's a truck coming into town tomorrow, carrying some precious cargo, and I know for a fact that it's going to have some mechanical troubles along the way.
The man is trying to play coy, but it's clear enough to you that he's planning to hijack a truck of whiskey and he's looking for a buyer. Well, is that so? Yeah, and I can arrange to take it over to your friend's garage on Clark Street. If you want the cargo, they'll probably pull in around 10.30 in the morning.
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Chapter 2: How did Al Capone's gang influence Chicago's bootlegging scene?
And how precious is this cargo? Oh, it's real precious, straight from Canada. You take a moment, because you're not sure what to do. Whiskey from Canada is high quality and fetches a good price. But having it fall in your lap like this seems a little too good to be true. It could be a setup.
Hey, look, if you're not interested, I've got other garages I can take this truck to for repairs, you know. No, no, no. It's fine. We want the business. 10.30 a.m., the garage on Clark Street. All right. Be sure to bring some strong guys, because there's a lot to unload. Will do. See you then. You feel a little uneasy as you hang up the phone, but you shake it off.
You're about to get your hands on the significant shipment of high-quality whiskey, which certainly makes you happy. And as you return to your ledger book, your eyes scan over the calendar on the wall. You realize that tomorrow is February 14th, Valentine's Day. Maybe this load of hijacked whiskey is Cupid's gift to you.
From Wondery, I'm Lindsey Graham, and this is American History Tellers, our history, your story. By the early 1920s, the city of Chicago had become the epicenter of bootlegging in the United States, and the various sophisticated criminal gangs in the city who imported and distributed illegal liquor were in an all-out war.
Armed with automatic Tommy guns, these rival gangs sprayed the streets of Chicago with bullets as they battled over territory. The city's murder rate skyrocketed, while gangsters paid politicians and police to look the other way, allowing them to operate with near impunity. The largest and most successful of these gangs was known as the Outfit, run by mobster Al Capone.
In late 1926, after leaders of the rival Northside gang made a brazen attempt on his life, Capone swore revenge, and by 1929 he'd killed or scared off all the Northside top lieutenants except for one, George Bugs Moran. That same year, on Valentine's Day, several members of Moran's gang were found gunned down in a garage.
The crime shocked the city, and Capone and Moran's rivalry led many to suspect that Capone had ordered the hit. Facing unprecedented public outrage over the crime, authorities became determined to get Capone however they could.
But lacking any real evidence to tie him to the murders, they knew they would have to take an unconventional approach if they were to have any hope of putting him behind bars. This is episode two in our two-part series on the St. Valentine's Day Massacre. Public Enemy number one. Imagine it's a little after 1030 in the morning on February 14th, 1929.
You're the leader of one of the biggest gangs in Chicago, and you're sitting in the front seat of a black sedan while a colleague sits behind the wheel. You're beating your fingers impatiently on your thigh as the driver waits for a delivery boy to cross the street carrying an armful of cut flowers. You reach across and honk the horn. Come on, move it. Let's go. Give the kid a break.
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Chapter 3: What happened during the actual St. Valentine's Day Massacre?
Finally, the delivery boy moves out of the way. All right, let's get going. And when we get there, I'll take care of paying for the goods. You guys just get unloading as fast as you can. Sure thing, boss. And I don't want to hear any yammering about their plans tonight. I don't care where they're going dancing or what dinner they're buying for the girls.
They take those crates off the truck as quickly as possible, and that's it. We have a lot to do today. I'm already behind schedule. All right, boss. All right, just relax. Don't tell me to relax. Time is money. Well, we're almost there. The car pulls onto Clark Street and you see the garage. A brick building with SMC cartage stenciled on the window.
But just as you pull up, a strange car parked outside catches your eye.
No, no, no. Dammit, keep driving.
Chapter 4: How did the public and authorities react to the massacre?
What's that? That's a police car parked out front. Keep driving.
Your colleague steps on the gas and passes the garage. You slam your fist into the side of the door. Oh, I knew it was too good to be true. A whole truck full of Canadian whiskey falling in my lap? Never should have trusted that no-good son of a gun. Well, boss, where do you want me to go now? Pull around the corner. There's nothing we can do but wait for them to leave.
Might as well grab a cup of coffee. We got six of our guys in there. It looks like they're going to have to spend Valentine's Day in jail. We'll get them out as soon as we can, though. Well, I guess it's a good thing we were running late, right? Otherwise, we'd be going to jail, too. You nod because your colleague has a point. Still, you're annoyed. You should have trusted your instincts.
All this competition among gangs might have worn you down, made you sloppy. And now you have to add bailing your guys out to an already busy day. On February 14, 1929, Bugs Moran, the powerful leader of the North Side Gang, narrowly managed to avoid what he thought was a shakedown.
After spotting a police car idling outside a garage where he'd been tipped off to a shipment of Canadian whiskey, Moran sped away. But meanwhile, a housewife named Jeanette Landsman, who lived in a neighboring apartment building, was ironing a pile of clothes when a series of loud bangs from the garage next door startled her.
Lansman had never heard a machine gun before, but she'd read plenty of descriptions of it in the newspaper, and every bone in her body told her that's what she'd just heard. She'd always suspected that the garage next door didn't really service cars. Men were frequently going at all hours of the night, and rarely did she see anyone working on automobiles.
She was pretty sure that the garage was a front for bootleggers, so if there was going to be a business nearby that would attract gunfire, SMC Cartage was it. After hearing what she believed was gunfire, she turned to her mother, who lived with her. She was sitting in a rocking chair next to the window, so Landsman asked her mother if she'd seen anything unusual.
Her mother said she saw what looked to be a detective car pull up to the building and then speed off. Lansman shook her head, confused, because as far as she knew, only gangsters carried machine guns, not police, and she was still sure that's what she heard.
So Lansman crept over to the window and peered out, just in time to see several men piling into a car, but they got in too fast for her to count how many. The car then peeled out and raced down Clark Street. Convinced that something really bad had happened in that garage, Lansman told her mother that she was going downstairs to get a better look,
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Chapter 5: What investigations were launched following the massacre?
He was a freelance sign painter who worked from home, meaning he was one of the only men in the apartment building at the time. Lansman asked him if he could go next door to check to see if anyone needed help. He might be strong enough to get the door open. McAllister agreed, and a few minutes later, he came running back up the stairs, his face ashen.
He yelled for Landsman to call the police, telling her there were a bunch of men next door who were all shot up. Landsman rushed back to her apartment and called the local police station located a half mile away. She begged them to send someone over as fast as possible.
The desk sergeant on duty thought she sounded hysterical and might be exaggerating, but he dispatched an officer to check things out anyway. At 10.45 a.m., Sergeant Thomas Loftus arrived on scene. He'd been in the station when Jeanette Lansman's call-in come in.
But the station's two patrol cars had been in use, so he had to hitch a ride in the truck of a telephone repairman who'd been working at the station. But almost exactly at the same time Loftus was dropped off, one of the station's patrol officers pulled up, having heard the call over the radio. Together, Loftus and the other officer approached the garage.
They could hear the dog barking and growling inside, and as they pushed open the door, Loftus was immediately hit by the smell of fresh blood. Not far from the door, Loftus could see a man, laying in a pool of blood, a snub-nosed revolver by his side. In the back of the room, there were six more men. One was sprawled across a chair, the other five were on the floor.
Their bodies were riddled with bullets, and there was blood everywhere. Most shockingly, two of the men's skulls were blown completely off. It was clear that whoever had killed these men had shot them at close range with powerful submachine guns.
In the dim light of the garage, Loftus could see there was something on the walls and floor mixed in with the blood, but couldn't tell exactly what it was. After a moment, he realized it was brain matter, and he staggered backwards, gagging. After 40 years on the police force, Loftus had seen plenty of dead bodies, including over the past several years since Tommy Guns had come to Chicago.
But this crime scene was different. He'd never seen this many victims with these kind of injuries all in one place. It looked like these men had been lined up against the wall and shot execution style. Loftus was shocked by the violence and carnage of the scene.
He quickly ordered the other officer to call the station in order to alert the deputy police commissioner and the Illinois Bureau of Investigation. But as Loftus turned to leave the garage, he heard a groan. He looked down and was shocked to discover that the man lying by the door was still alive.
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Chapter 6: How did the media coverage impact public perception of gang violence?
Loftus yelled out for the other officer to tell the station to send a police wagon to take this man to the hospital. And as Loftus bent over to examine the victim's injuries more closely, he realized that he recognized the wounded man as a young member of the Northside gang named Frank Gusenberg. Loftus asked him what had happened. Gusenberg croaked out that cops had done it.
That didn't make sense to Loftus. He pushed Gusenberg for more information, but Gusenberg refused to say anything else, only whispering, I won't talk twice. Loftus knew it was a point of pride amongst gangsters that they didn't rat each other out. They maintained a code of silence, solving their disputes with each other by themselves rather than involving law enforcement.
But he hoped the brutality of this crime would change Gusenberg's mind and implored him again to tell him what had happened. But Gusenberg wouldn't say anything about who had shot him. So Loftus turned his attention to the man's injuries. It was clear he was in bad shape. He assured Gusenberg that a wagon was coming to get him to the hospital.
And realizing that if Gusenberg was still alive, there might be other survivors, Loftus went to check on the other bodies. He took the pulses of all the remaining men, except the two who had suffered head injuries too severe to have survived. Loftus confirmed they were all dead. He recognized one of the victims as Frank Gusenberg's older brother.
The others, though, he didn't know or couldn't identify due to the wounds. After confirming there were no other survivors, Loftus then found the barking dog who was tied to the axle of a truck in the garage. He had tried to approach the animal but backed away when the dog growled and snapped at him.
When the police wagon finally arrived, Loftus helped them load Frank Gusenberg and instructed them to take him to a nearby hospital as fast as possible. Gusenberg had so many bullet holes in his body, Loftus could hardly believe he was still alive. He knew he didn't have much time. And when the wagon drove away, that left Loftus alone at the crime scene.
While the police and the public had become accustomed to the violence and corruption that had plagued Chicago for years, Loftus knew this crime was different. It had all gone too far. If someone was willing to massacre men and create this much carnage, what else were they capable of? They had to be stopped and made to pay for their crimes.
But that meant figuring out who had done this, and it also meant making sure justice was served. But at that moment, both tasks felt nearly impossible. Hello, American History Tellers listeners. I have an exciting announcement. I am going on tour, coming to a theater near you. The very first show will be at the Granada Theater in Dallas, Texas on March 6th.
It's going to be a thrilling evening of history, storytelling, and music with a full band behind me as we look back to explore the days that made America. and they aren't the days you might think. Sure, everyone knows July 4th, 1776, but there are many other days that are maybe even more influential.
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Chapter 7: What strategies did law enforcement use to target Capone?
Go to AmericanHistoryLive.com. On the morning of February 14th, 1929, word of the massacre at the garage on Clark Street began to spread throughout Chicago. Police detectives soon arrived on the scene, and passersby gathered on the street, eager to find out what was going on. A delivery driver for the Chicago Daily News noticed the commotion while he was dropping off papers in a nearby store.
He gleaned that there was a shooting, and judging by the police presence, a bad one. So he borrowed the shop owner's phone and called the newsroom. The city editor quickly dispatched a photographer to the scene. And soon, photographers and reporters from the four daily newspapers that serve Chicago all arrived and began documenting the entire gruesome array.
One photographer set his camera up at the very back of the garage in order to get the whole space in his shot. Two other photographers set up a tripod on top of a parked car in order to get the highest possible angle. Meanwhile, reporters pestered the police for information, but they had nothing to give them.
Officers fanned out to nearby buildings to interview anyone who might have been a witness. Sergeant Thomas Loftus, one of the first officers on the scene, eventually left to go to the hospital where the lone survivor Fred Gusenberg had been transported. When he arrived, he learned that Gusenberg was still alive, but barely.
Another officer had questioned him, but he'd again refused to identify the assailant. And when asked who had shot him, he responded that nobody had. He died at 1.30 p.m., approximately three hours after the shooting. By the time Loftus returned to the crime scene, the police commissioner William Russell and coroner Herman Boondenson had arrived.
The first reporters on the scene had already rushed off to file their stories, and detectives collected bullet casings while the coroner prepared to transfer the bodies to the morgue. Loftus was struck by the silence.
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Chapter 8: What were the long-term effects of the massacre on organized crime in Chicago?
In his experience, police officers usually cracked wise at murder scenes, attempting to bring levity to what was otherwise a dark undertaking. But this scene was too gruesome for jokes. Loftus watched as each victim was loaded into a police wagon and taken away where coroner Herman Budenson began the process of identifying the bodies.
He soon ascertained that five of the six men were known members of the Northside gang, while the sixth was a local optician who hung around the bootleggers almost like a groupie. With the identities of the men known, it seemed clear that this shooting was an attempt to wipe out the Northside gang. But there was a problem with the theory.
The leader of the Northsiders, George Buggs Moran, was not among the men killed. Police officers canvassing the neighborhood learned that, curiously, on the morning of the murders, witnesses observed men dressed like police getting into cars with men dressed like mobsters.
This led police to believe that Moran may have been kidnapped, and many suspected that his body would soon turn up in a ditch. And while authorities continued to try to determine the motive for the crime, the public was learning the gruesome details.
Thanks to the haste of the photographers and reporters who rushed to the scene, photos of the massacre were plastered across the Chicago papers within just hours of the shooting. The images were shocking. The articles that accompanied the photos described the event as heinous and one of the most cold-blooded gangland massacres in Chicago's history.
After years of gunshots echoing through the streets and gangsters seemingly never held accountable for their actions, the brutality of this crime, laid out in black and white in graphic photos on the front page, made the violence impossible to ignore. Chicago law enforcement knew that they needed to respond.
But while it seemed clear that this was yet another battle in the gang wars, there was almost no evidence as to which gang had perpetrated it. Nevertheless, theories abounded. Some people thought the Purple Gang, who operated out of Detroit, were making a move into Chicago. Others believed it was the result of a falling out between the Northsiders and the Sicilian Gang.
Still others thought it was a hijacking gone wrong or merely a continuation of the war between Al Capone's outfit and the Northsiders. Regardless of who was responsible, authorities were not going to let this one get brushed under the rug. The police, the state attorney, and Coroner Boondinson all launched investigations. As coroner, Bundensen wasn't just responsible for examining corpses.
The Illinois Constitution required that coroners investigate unnatural deaths and determine a cause by holding inquests. Bundensen took his job seriously and was determined to do a proper investigation. And as an elected official, he was keenly attuned to public perception. He knew with such a shocking crime the public would demand action and wanted law enforcement to crack down.
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