Transcript

St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers

From American History Tellers · Episode page · Watch on YouTube

· 39 min · 7,101 words · 63 timestamped sections

This is the full, timestamped transcript of "St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers", an episode of American History Tellers published February 13, 2026 (39 min, about 7,101 words). It mentions 17 people, works and ideas, including Chicago, Al Capone, George Bugs Moran, Clark Street, Herman Bundenson.

What this episode is about

The St. Valentine's Day Massacre occurred on February 14, 1929, marking a pivotal moment in the violent turf war between Chicago's rival gang leaders, particularly against Al Capone's faction. As one gang leader grapples with the pressures of bootlegging and the betrayal inherent in organized crime, the massacre epitomizes the brutal realities of gang rivalries and the fallout from illicit operations during Prohibition.

Key takeaways

  • In 1920s Chicago, whiskey sales outshone flowers because prohibition turned gangsters into the world's unlikeliest florists.
  • Valentine's Day? More like 'Valentine's Day of the Dead'—Al Capone’s brutal business acumen brought new meaning to romance.
  • Trust in crime is scarce; the only thing less reliable than your bootlegging associate is your math skills.
  • The St. Valentine's Day Massacre taught us: sometimes love might just get you killed—especially in the mob world.
  • Gang-related business strategies? Count on chaos rising faster than profits, proof that crime rarely pays without a bloody price.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Chicago, Al Capone, Clark Street, George Bugs Moran
  2. – 10:00: Clark Street, Janette Lansman, Thomas Loftess
  3. – 15:00: Chicago, Frank Guzenberg, Clark Street
  4. – 20:00: Chicago, Al Capone, George Bugs Moran, Herman Bundenson
  5. – 25:00: Chicago, Al Capone, Clark Street, Miami
  6. – 30:00: Chicago, The St. Valentine's Day Massacre, Al Capone, Mabel Walker Willibbrandt
  7. – 35:00: Chicago, Al Capone, The St. Valentine's Day Massacre
  8. – 38:37: Chicago, Al Capone, The St. Valentine's Day Massacre, George Bugs Moran

Notable quotes from "St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers"

  • 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.
    about Chicago · at
  • On February 14th, 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.
    about George Bugs Moran · at
  • Realized that he recognized the wounded man as a young member of the North Side gang named Frank Guzenberg. Loftess asked him what had happened. Gusenberg croked out that cops…
    about Frank Guzenberg · at
  • 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 passers by gathered on the street, eager to find out what was.
    about Clark Street · at
  • The shooting. By the time Loftess returned to the crime scene, the police commissioner William Russell and coroner Herman Bundenson had arrived. The first reporters on the…
    about Herman Bundenson · at
  • McCormack and the others told the president that crime was out of control in their city and that the local government was too corrupt to make meaningful change. They argued that only.
    about Robert McCormack · at
  • Didn't taxation inherently legitimize the activity? But Willibbrandt had an ally in Chicago, a US attorney named George Emerson Johnson. And a few days after the St. Valentine's Day massacre, Johnson issued Capone a subpoena to.
    about Mabel Walker Willibbrandt · at
  • The St. Valentine's Day Massacre by William J. Helmer and Arthur J.
    about The St. Valentine's Day Massacre · at

Who and what is mentioned in this episode?

People

  • Al Capone — Person · Primary antagonist / central historical figure · 11 mentions · first at
    Leader of Chicago's Outfit and the main suspected orchestrator of the St. Valentine's Day Massacre; later pursued and convicted for tax evasion.
    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…
  • George Bugs Moran — Person · Primary rival / intended target who survives · 3 mentions · first at
    Leader of the North Side gang and Capone's chief rival; he narrowly avoids the garage and later publicly implies Capone was responsible.
  • Herman Bundenson — Person · Coroner leading inquest and public reenactment · 1 mention · first at
    Cook County coroner (as described) who runs an inquest, convenes jurors, and stages a reenactment to investigate and reassure the public.
  • Mabel Walker Willibbrandt — Person · Federal legal strategist (referenced expert/official) · 1 mention · first at
    Assistant Attorney General who champions the strategy of prosecuting Capone for tax evasion when direct evidence for the massacre is lacking.
  • Frank Guzenberg — Person · Victim / lone survivor (briefly) and key witness who refuses to talk · 3 mentions · first at
    North Side gang member found alive at the scene; questioned by police but maintains silence and dies hours later, limiting evidence.
  • Thomas Loftess — Person · First responding officer / on-scene investigator · 2 mentions · first at
    Police sergeant who arrives at the garage, discovers the bodies, identifies Guzenberg, and initiates official response and notifications.
    In one place. It looked like these men had been lined up against the wall and shot execution style. Loftess was shocked by the violence and carnage of the scene. He quickly…
  • Janette Lansman — Person · Civilian witness / reporting party · 2 mentions · first at
    Neighbor who hears what she believes is machine-gun fire and triggers the police response by seeking help and calling the station.
    But meanwhile, a housewife named Janette Lansman, 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.
  • Robert McCormack — Person · Civic power broker pushing federal intervention · 1 mention · first at
    Owner of the Chicago Tribune who leads businessmen to Washington to pressure President Hoover for federal action against Chicago crime.
  • William Russell — Person · Senior city official at scene (referenced) · 1 mention · first at
    Identified as the police commissioner who arrives at the crime scene as the investigation escalates.
    The shooting. By the time Loftess returned to the crime scene, the police commissioner William Russell and coroner Herman Bundenson had arrived. The first reporters on the…
  • Anton Surerach — Person · Reform mayor (referenced outcome/fallout) · 1 mention · first at
    Named as the reform candidate elected mayor in 1931 as part of the political fallout from gang violence and public demand for cleanup.
    Crime would continue to have a lasting impact on Chicago and the country. In 1931, Chicago elected Democrat Anton Surerach as mayor. Surerac ran as a reform candidate who could…

Books & papers

  • The St. Valentine's Day Massacre — Book · Primary recommendation · 7 mentions · first at
    This book is recommended for learning more about the St. Valentine's Day Massacre.
  • Dedra Bear — Book · Primary recommendation · 1 mention · first at
    Dedra Bear's book is recommended for learning more about Al Capone and the Chicago Gang Wars.
    If you'd like to learn more about Al Capone and the Chicago Gang Wars, we recommend Al Capone, the life, legacy, and legend by Dedra Bear.
  • Murder and Mayhem on Chicago's North Side — Book · Primary recommendation · 1 mention · first at
    This book is recommended for learning more about the violence and gang activities on Chicago's North Side.
    Bilick, and Murder and Mayhem on Chicago's North Side by Troy Taylor.

Companies & orgs

  • Loyola Law School — Company · Referenced work · 1 mention · first at
    Loyola Law School's dean was part of the panel of jurors for the inquest into the St. Valentine's Day Massacre.
    Incorruptible, including company presidents, lawyers, court officials, and the dean of Loyola Law School, among others. But then he went even further, announcing that he would…

Places & events

  • Chicago — Place · Setting · 31 mentions · first at
    Chicago is the primary location where the events of the St. Valentine's Day Massacre and the gang wars took place.
  • Clark Street — Place · Setting · 6 mentions · first at
    Clark Street is the location of the garage where the St. Valentine's Day Massacre occurred.
  • Miami — Place · Setting · 2 mentions · first at
    Miami is where Al Capone had a house and was staying during the time of the St. Valentine's Day Massacre, providing him an alibi.
    On March 20th, 1929, Al Capone returned to Chicago from Miami to face questions from a grand jury about bootlegging and the money he made from it. Capone wasn't especially worried, though. For years,.

Full transcript with timestamps

Wonder. 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 5 years, you've been embroiled in a turf war against a gang based on the southside 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 koi, 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.

Uh, 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 it's 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 cuz there's a lot to unload. We'll 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 highquality 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 commie guns, these rival gangs sprayed the streets of Chicago with bullets as they battled over territory. The city's murder rates 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 North Side 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 10:30 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 arm full of cut flowers. You reach across and honk the horn.

Come on, move it. Let's go. Uh, give the kid a break. It's Valentine's Day. Probably his busiest day of the whole year. Well, I'm busy, too. Your day is packed. Right now, you're supposed to be meeting a truck full of stolen liquor, but you're running late. 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 stencled on the window. But just as you pull up, a strange car parked outside catches your eye. No, no, no. Damn it. Keep driving. 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. I 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, and 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. 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 14th, 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 Janette Lansman, 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 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, Lansman 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. As she made her way down the two flights of stairs and walked next door, she could hear a dog howling inside the garage.

She stood on her tiptoes and tried to look in the window, but couldn't see anything. She called out, but no one answered. And when she tried to push the door open, she found it was stuck. Scared, she rushed back to her apartment building and knocked on the door of one of her neighbors, a man named Clare Mallister. 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.

Mallister agreed and a few minutes later he came running back up the stairs, his face ashing. He yelled for Lansman to call the police, telling her there were a bunch of men next door who were all shot up. Lansman 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 Loftess arrived on scene. He'd been in the station when Janette Lansman's calling 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 had been working at the station. But almost exactly at the same time Loftess was dropped off, one of the station's patrol officers pulled up, having heard the call over the radio.

Together, Loftess and the other officer approached the garage. They could hear the dog barking and growling inside. And as they pushed open the door, Loftess was immediately hit by the smell of fresh blood. Not far from the door, Loftess 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. 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, Loftess 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, Loftess 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. Loftess 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 Loftess 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. Loftess yelled out for the other officer to tell the station to send a police wagon to take this man to the hospital. And as Loftess bent over to examine the victim's injuries more closely, he realized that he recognized the wounded man as a young member of the North Side gang named Frank Guzenberg. Loftess asked him what had happened. Gusenberg croked out that cops had done it. That didn't make sense to Loftess. He pushed Gutenberg for more information, but Gutenberg refused to say anything else, only whispering, "I won't talk." twice.

Loftess 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 Gutenberg's mind and implored him again to tell him what had happened. But Gutenberg wouldn't say anything about who had shot him. So Loftess turned his attention to the man's injuries. It was clear he was in bad shape. He assured Gutenberg that a wagon was coming to get him to the hospital. And realizing that if Gutenberg was still alive, there might be other survivors, Loftess 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.

Loftess confirmed they were all dead. He recognized one of the victims as Frank Guzenberg'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, Loftess 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, Loftess helped them load Frank Guzenberg and instructed them to take him to a nearby hospital as fast as possible.

Gutenberg had so many bullet holes in his body, Loftess could hardly believe he was still alive. He knew he didn't have much time. And when the wagon drove away, that left Loftess 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, Loftess 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, 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.

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 passers by 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 at 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 served 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 Loftess, 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 Gutenberg was still alive, but barely. Another officer had questioned him, but he' again refused to identify the asalent, and when asked who had shot him, he

responded that nobody had. He died at 1:30 p.m. approximately 3 hours after the shooting. By the time Loftess returned to the crime scene, the police commissioner William Russell and coroner Herman Bundenson 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 morg. Loftess was struck by the silence. 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.

Loftess 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 north side gang while the sixth was a local optician who hung around the bootleggers almost like a groupy. With the identities of the men known, it seemed clear that this shooting was an attempt to wipe out the North Side gang. But there was a problem with the theory. The leader of the Northsiders, George Bugs Moran, was not among the men killed.

Police officers canvasing 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 continue 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 and 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 [snorts] 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 Bundenson all launched investigations. As coroner, Bunden wasn't just responsible for examining corpses. The Illinois Constitution required that coroners investigate unnatural deaths and determine a cause by holding inquests. Bundinson 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. So hours after the massacre occurred on the afternoon of February 14th, 1929, Bundenson picked up the phone and began rounding up a panel of

jurors for his inquest. To ensure the inquiry was above reproach, he chose highly respected Chicago businessmen with sterling reputations for being incorruptible, including company presidents, lawyers, court officials, and the dean of Loyola Law School, among others. But then he went even further, announcing that he would be conducting a reenactment of the shooting at the crime scene. The next day, he shephered the six members of the jury into the SMC Cartage garage. Along with the jury members, the police, police commissioner, members of the Justice Department, and press all packed the garage, eager to watch the drama unfold.

There were so many people that they were forced to huddle together in order to avoid stepping in the sticky puddles of drying blood still on the floor. Bundenson cast detectives to play the victims. And as a doctor from his office read aloud the report Bunden had written, Bundenson poked the detectives where each bullet had hit the victim they were portraying. He even brought the dog back to contribute to the veracity of the reenactment. Despite all these theatrics, though, not much information was learned from the demonstration. Lunenson vowed to keep the inquest going though and to continue to question witnesses until they got answers. In the meantime, the newspapers covered the reenactment in detail, helping satiate the public's desire for a robust response to the murders. But the police and state attorney's office were also quick to assure the public that they were taking action, too,

promising a raid to crack down on bootlegging and turn Chicago dry to widespread corruption. For years, law enforcement had turned a blind eye to the illegal sale of alcohol. Also, with roughly 10,000 establishments selling alcohol in Chicago, authorities knew it would be virtually impossible to shut them all down. Furthermore, some authorities believe that allowing a black market in alcohol actually prevented other crimes. By some estimates, there were 30,000 people employed through bootlegging in the city. If those people were suddenly out of work, authorities worried that crime could actually get worse. But in the aftermath of the carnage of the Valentine's Day massacre, it was clear to many that the days of rampant and unchecked bootlegging in Chicago were over. The public wanted the city cleaned up and the violence to stop. And many prominent Chicago business owners came forward to pressure the government to

act, arguing that the city's reputation for violence was costing them business. As a result of this public pressure, the state attorney issued an edict to the local speak easy owners to close up shop or go to jail. In response, many establishments put padlocks on their front doors, though they continued to find ways to serve their regular customers. Meanwhile, the police commissioner ordered all the usual suspects be rounded up and questioned by both the coroner and the police. But even after this initial flurry of activity, the reenactment, the crackdown on the speak easys, and the roundup of known gangsters, it became clear that little progress had actually been made.

After several days, the police were still in the dark about who was behind the shootings, and authorities had another concern. The whereabouts of the leader of the North Side gang, Bugs Moran. The original theory that Moran had been kidnapped was disproven after he sent a message to one of the lead detectives claiming that he didn't know who had orchestrated the shooting. It became clear that Moran was in hiding, but the police had no idea where. Instead, a clever member of the press had managed to track him down.

Imagine it's midFebruary 1929. You're a journalist with one of Chicago's major newspapers and you're walking down a hallway of a hospital in Evston, Illinois, approximately 15 mi north of Chicago. You hurry past a nurse who's eyeing you suspiciously and then duck into a room. A broad shouldered man in his 30s with light brown wavy hair is lying in the bed. He waves his hand, gesturing for you to leave. Hey, this is a private room. Get out of here. Hey, relax, Bugs. I just want to talk to you. Who are you calling Bugs? I don't know anyone named Bugs. I'll give it a rest.

I know who you are. I'm telling you, you got the wrong guy. I'm I'm just an ordinary Joe with the flu. I need my rest. Scram. You approach the bed. Look, I can make a call right now. Tip off the police or your enemies, or you can talk to me, and no one will know about this until the evening paper comes out, giving you plenty of time to move on. man glares at you for a moment. And for a second, you think he might punch you. But then he relents. All right, fine. You found me, but you're wasting your time. I don't know anything. But you got to know something. I'm in the dark as much as you are. I have no idea what brought this on. Okay, what do you think then? Was it the purple gang? Are they making a move into Chicago? I'm telling you, I don't know. What about Capone?

Everyone knows you guys have been going at it for years. How many more times can I say I don't know. I don't know. Oh, come on. This isn't the time for code of silence. Someone blew your guys to smitherines. There were brains all over the floor. You got to give me something. Moran crosses his arms and shrugs dramatically. Even if I wanted to help you, I can't tell you what I don't know. Remember, Bugs? One call and I let everyone know where you are. Give me something so I can put it in the paper. Oh god. Fine. You know what I think? It was vicious and cold bloodooded. Only Capone kills like that. You scribble down the quote in your notebook and bowl for the door. That's it. Thanks, bugs.

You have to rush back to Chicago to get this story filed. Bugs Moran going on the record and accusing Capone is big news. So big that you wonder if this might be the break that cracks the case. After a reporter managed to track Bugs Moran down in a local hospital where he was hiding out figning the flu, Moran made a shocking statement. He all but accused his rival Al Capone of orchestrating the massacre at the Clark Street garage. And Moran's quote about Capone caused an immediate stir. But little did Moran know, Capone had an airtight alibi for the day of the massacre. Capone was in Miami, Florida.

He bought a house on Palm Island the previous summer and had been spending significant time there. Back in Chicago, the investigation into the massacre dragged on with little progress, and the city's elite grew impatient with the inability of local law enforcement to bring order. So, within a month of the shooting, Colonel Robert McCormack, the owner of the Chicago Tribune, gathered a small group of businessmen and traveled to Washington, DC. There they secured a meeting with President Herbert Hoover. McCormack and the others told the president that crime was out of control in their city and that the local government was too corrupt to make meaningful change. They argued that only the federal government, who were outside the influence of the gangsters, could bring order to the city. They pressured the president for help, even suggesting he send troops to Chicago. Following this meeting with McCormack, Hoover

dispatched federal agents to Chicago, but they faced the same problem the local police did. They could not find sufficient evidence that Capone had ordered the massacre. But federal authorities were not going to let that deter them. They still wanted Capone locked up. As far as they were concerned, he was public enemy number one. And even if they couldn't pin the massacre on him, maybe they could get him for something else. Leading the charge was United States Assistant Attorney General Mabel Walker Willibbrandt. As a young woman, Willibbrandt had taken night classes at the University of Southern California, earning her law degree before accepting a position as a public defender for women in Los Angeles. There, she handled over 2,000 cases, building a strong reputation. And by 1921, legal and political leaders in California recommended her for assistant attorney general in the Harding administration.

This made her the highest ranking woman in the federal government at the time. And throughout the 1920s, she led vigorous enforcement of prohibition laws. But after several frustrating years of failing to put away gangsters like Capone, Willer Brandt knew she had to come up with a different strategy. It was clear that Capone and other gangsters were getting rich from their illegal activities and they weren't paying any taxes on their earnings either. So, Will Brandt decided they would go after Capone for tax evasion.

At the time, it was a novel legal approach and many other lawyers initially dismissed it as ridiculous and paradoxical. How could the government tax income that was illegally attained? Didn't taxation inherently legitimize the activity? But Willibbrandt had an ally in Chicago, a US attorney named George Emerson Johnson. And a few days after the St. Valentine's Day massacre, Johnson issued Capone a subpoena to testify in front of a federal grand jury. The subject wasn't the massacre, but rather his income. But while Capone may have been surprised by this shift in the federal government's tactics, he refused to be intimidated. He had lived much of his life impervious to the law, and he had no plans to stop now.

On March 20th, 1929, Al Capone returned to Chicago from Miami to face questions from a grand jury about bootlegging and the money he made from it. Capone wasn't especially worried, though. For years, the government had him in their sights and failed to pin anything on him, so what would be different now? In fact, he was so dismissive of the grand jury subpoena that he arrived back in Chicago a day later than he was supposed to appear, leading the court to hold him in contempt. In the end, Capone answered the government's questions for 80 minutes and then came back a week later to sit for another hour. When it was over, Capone reported to jail to serve his 1-day sentence for contempt, but he seemed otherwise unbothered. This was just another annoyance that was now behind him. But inside the halls of government, the machinery was turning.

President Herbert Hoover was now embracing Assistant Attorney General Mabel Walker Wilderbrand strategy to use unpaid income tax to bring down Capone. He appointed Treasury Secretary Andrew Melon to oversee the investigation, who sent in a team of IRS agents to start building a paper trail that could be used to charge Capone with a federal crime. Oblivious to the government's investigation, Capone got back to work. He had been in Florida for several months, and there was a lot to do to put his outfit back in order. Capone's rival gang, the Northsiders, may have been irreparably damaged by the St.

Valentine's Day massacre, but the Sicilians were still causing problems, and Capone had a list of his own guys who he felt had betrayed him while he was away in Miami. There were also bigger problems on the horizon. For years, it had been clear that America's experiment with prohibition was a failure. Instead of curbing alcohol sales and solving society's ills, as its advocates had hoped, it had done the opposite. More bars and clubs filled Chicago than ever before, though they operated illegally. Crime was up and prohibition was rapidly losing popularity. So, Capone and other gangsters who had profited mighty from the alcohol ban could see the writing on the wall. The end was coming and with it their main income stream. Knowing they had to find a solution sooner rather than later, in mid-May 1929, gangsters from several cities, including New York, Philadelphia, and Chicago, gathered in Atlantic City. The main item

on the agenda was how to work together to blunt the financial impact the repeal of prohibition would bring, as well as a discussion of how to stop the ongoing bloodshed. But when Al Capone and three trusted advisers arrived for the gathering, they didn't receive a warm welcome. Imagine it's May 15th, 1929. You slide into a booth at the back of a speak easy in Atlantic City. A waiter brings over two glasses of whiskey without you even having to order. It's clear he knows you're one of the top gangsters in New York City here for the important meeting. A moment later, Al Capone swans in, waving a cigar and barking at the bartender. You roll your eyes because wherever this guy goes, he just has to be the center of attention. You've had enough of his ego and you're here tonight to put him back in line. The pone takes a seat across from you. To what do I owe the pleasure of this sit down? We need to talk, Al. You're

bringing too much attention on us. If you wanted the spotlight so badly, you should have been a singer. Well, maybe I'll do that next. This is no joke. We're at a pivotal moment here. The future of our business is at stake. We need to all work together. And you've got everyone bent out of shape. I'm just handling my business. Oh, your business. We all saw the photos in the paper. Jeez, on Valentine's Day? That's well beyond handling business. Well, hey, no one's been able to pin that on me. I was in Florida. It doesn't matter. It happened in your city. Or are you telling me you don't have control of your turf? I'm not saying anything.

You're just running too hot out. If it wasn't this massacre, it'd be something else. Too much bloodshed. We need to make it stop if we want to keep business running smoothly. I thought that's what we're all doing here in Atlantic City. Figure out how to all work together. I fully support ending the unnecessary violence. It's too much. There's plenty of money to go around. Well, yeah. Well, after everything that's happened, it's hard for anyone to believe you, Al. No other city has as much murder as Chicago. There are a lot of gangsters in Chicago. What can I say? You can't lay it all on me. Well, it's not just the violence. You're in the paper every day.

And the spotlight's not just on you. It shines on us, too. We're a business that works better in the shadows, you know. Well, what do you want me to do? The press just loves me. I can't take two steps without a reporter sticking their pen in my face and asking for a quote. Do what the rest of us do and don't talk to them. All right. All right. I'll keep a tight lift. You shift in your seat. Well, good. But that's not going to be good enough. You need to lie low. This Valentine's massacre stuff needs to blow over. Stay out of the paper. Give us some time to get our national syndicate set up. And how do you expect me to do that? Well, [clears throat] you're a smart man. You'll figure it out.

Otherwise, you might be lying really low, if you know what I mean. You stand up, throw some money on the table for the drinks, and walk out, leaving Al Capone sitting alone in the booth. You doubt you can convince Capone to stay out of the limelight forever. But you sincerely hope that this is the last you see of him for a long time to come. Under pressure from other gangsters and still facing retaliation threats for the St. Valentine's Day massacre back in Chicago. Capone came up with a plan to temporarily step aside and give law enforcement what they wanted too. He would turn himself in. On the way back to Chicago, Capone and his bodyguard made a stop in Philadelphia. They got off the train, had a meal, and went to a movie. As they walked out of the lobby, Capone was greeted by a detective he knew. This man frisked him and while ordinarily Capone didn't carry a gun, letting his bodyguard do it. When the

detective patted Capone down, he found a weapon. Capone was arrested for illegal possession of a firearm. And within 16 hours, he was convicted and sentenced to one year in the Eastern State Penitentiary. In prison, Capone received a private cell and was able to continue to conduct business from inside. But he done as he promised and found a way to lay low. He was released in March 1930, 2 months early for good behavior. After his release, Capone returned to Chicago, confident that life would return to normal, the way it was before St.

Valentine's Day 1929. But he was wrong. During his time in prison, the outrage over the shooting had not blown over. In fact, the scrutiny had only increased so that now Capone found himself under constant police surveillance. Furthermore, federal agents had begun coming after his top associates, including his older brother Ralph, for tax evasion. And to everyone's surprise, they were getting results. For the first time, charges were starting to stick and gangsters were being sentenced to lengthy prison sentences. Finally, on October 6th, 1931, Capone himself was arrested. Just 11 days later, he was convicted on five counts of evading taxes and two counts of failing to file tax returns. He was sentenced to 11 years in federal prison. And this time there was nothing Capone could do. He was going away and he knew it.

Meanwhile, authorities had yet to determine who was responsible for the St. Valentine's Day massacre. But in the years to come, the fallout from the crime would continue to have a lasting impact on Chicago and the country. In 1931, Chicago elected Democrat Anton Surerach as mayor. Surerac ran as a reform candidate who could clean up city hall and stop gangsters from running roughshot over the city. Chicago was ready for change, so Surerach won with over 80% of the vote. Serious reform occurred at the federal level as well.

In 1932, Franklin Roosevelt was elected president. He ran in part on stopping crime, including the gangland murders in Chicago. And once in office, he took several steps to achieve this goal. On March 22nd, 1933, just 18 days after his inauguration, Roosevelt signed the Cullen Harrison Act, which legalized the sale of beer and wine. And only 6 months later, the states had ratified the 21st Amendment, repealing prohibition. Alcohol was once again legal in the United States. A year later, Roosevelt signed the National Firearms Act of 1934, banning the private sale of the Tommy gun. It was the first federal gun control law passed in the country. And in the wake of these reforms, crime began to wne. Over the course of the 1930s, the murder rate in Chicago fell to half of what it had been during the 1920s. While these reforms were underway, and as Al Capone, sat in prison, one of his top lieutenants,

Frank Niti, took over as the head of the outfit. After the repeal of prohibition, Nidi refocused the outfit's business on the fundamentals of rakateeering, gambling, and lone sharking, and he wisely decided to keep a much lower profile than Capone. As time went on, Chicago's other gangsters refocused as well. With Capone out of the picture, Bugs Moran tried to take back control of the north side, but ultimately the outfit under Niti remained too strong. Moran would never regain his whole turf and he ended up leaving Chicago. He was arrested in Ohio for robbery in 1946 and died in prison in 1957. In 1934, Al Capone was transferred to Alcatraz Federal Penitentiary. While confined there, he suffered from a mental breakdown, likely as a result of the harsh conditions exacerbated by an advanced case of syphilis. He was parrolled in 1939 and died at his home in Florida in 1947 at just 48 years old.

In the end, no one was ever charged with the St. Valentine's Day massacre. Even though it horrified Chicago, gripped the nation, energized the federal government, and had two presidents trying to get Capone, this violent mass murder remains unsolved. From Wonder. This is episode two of our two-part series on the St. Valentine's Day massacre from American history tellers. In our next episode, we'll explore Capone's ultimate downfall with Jonathan Ike, author of Get Capone: The Secret Plot That Captured America's Most Wanted Gangster.

If you'd like to learn more about Al Capone and the Chicago Gang Wars, we recommend Al Capone, the life, legacy, and legend by Dedra Bear. The St. Valentine's Day Massacre by William J. Helmer and Arthur J. Bilick, and Murder and Mayhem on Chicago's North Side by Troy Taylor. American History Tellers is hosted, edited, and produced by me, Lindsey Graham, for Airship. Audio editing by Muhammad Shazi. Sound design by Molly Bach. Music by Throne. This episode is written by Austin Racklas, edited by Dorian Marina, managing producer Desi Bllelock, senior producers Alita Rosanski and Andy Beckerman. Executive producers are Jenny Lowour Beckman and Marshall Louie for Wondery.

Questions about this episode

Who speaks in "St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers"?

Lindsey Graham (Host), Al Capone (Guest), Bugs Moran (Guest), Janette Lansman (Guest), Thomas Loftess (Guest), Mabel Walker Willibbrandt (Guest).

What is "St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers" about?

The St. Valentine's Day Massacre occurred on February 14, 1929, marking a pivotal moment in the violent turf war between Chicago's rival gang leaders, particularly against Al Capone's faction. As one gang leader grapples with the pressures of bootlegging and the betrayal inherent in organized crime, the massacre epitomizes the brutal realities of gang rivalries and the fallout from illicit…

What is mentioned in this American History Tellers episode?

17 people, works and ideas are mentioned, including Chicago, Al Capone, George Bugs Moran, Clark Street, Herman Bundenson, Mabel Walker Willibbrandt. Each one on this page links to its own page with every episode that mentions it.

How long is "St. Valentines Day Massacre | Public Enemy No. 1 | American History Tellers"?

The episode runs 39 min; the transcript is about 7,101 words in 63 timestamped sections.

More from American History Tellers

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated February 15, 2026.