Episode 4: Bootleggers, Tommy Guns, and Bad Timing: The St. Valentine's Day Massacre
A Chicago garage. Seven men against a wall. The rat-tat-tat of Thompson submachine guns. By the time the smoke cleared on Valentine's Day 1929, six were dead, one was dying, and America would never view organized crime the same way again.
The St. Valentine's Day Massacre stands as the bloody crescendo of Prohibition-era violence – a carefully orchestrated hit that revealed the dark underbelly of America's failed experiment with legislating morality. But why did this particular gangland execution capture public imagination and reshape national policy when so many others faded into history?
Chicago's transformation provides our first clues. A booming industrial center rebuilt after devastating fire, the city attracted waves of immigrants seeking opportunity but finding discrimination. In these marginalized neighborhoods, protection rackets evolved into sophisticated criminal organizations, with Al Capone and Bugs Moran emerging as rival kings of the underworld. Their battle for control of Chicago's bootlegging empire would culminate in that blood-soaked garage, though ironically, Moran himself escaped death by simply running late.
The massacre's aftermath proved equally fascinating. While widely believed responsible, Capone maintained the perfect alibi – he was in Florida with his attorneys. No one was ever convicted for the brutal killings, yet the public outrage helped cement Prohibition's failure and caught President Hoover's attention. Federal authorities, unable to pin the murders on Capone, eventually imprisoned him for tax evasion instead – a strange justice for a man responsible for countless deaths.
Beyond the blood and bullets, this episode reveals how failed reform creates unexpected consequences, how violence shapes public opinion, and how sometimes the most violent criminals fall to the most mundane charges. Join us for this exploration of the crime that changed America's relationship with organized crime forever.
Transcript
What follows is a brutal execution. A hail of gunfire that leaves them all but one of them dead.
Alana:This is the St. Valentine's Day massacre, one of the most infamous crimes in American history. It wasn't just a gangland hit.
It became a turning point in how Americans viewed organized crime. And we're here to unravel the story behind the blood in the snow.
Michael:Welcome to history's Greatest crimes, where we two historians dive into the most infamous crimes in history, peeling back the layers to understand their causes, their impact, and what they reveal about the world we live in today. I'm Michael.
Alana:And I'm Alana. This wasn't just a random act of violence. It was a carefully orchestrated power move during one of America's most exciting and yet turbulent times.
Prohibition.
Michael:Exactly.
Al Capone and Bugs Moran, two of the most famous and infamous figures in organized crime, were locked in a battle for control over Chicago's lucrative bootlegging trade. The massacre was the result of that rivalry. But the story doesn't end there.
Alana:So who pulled the trigger? What was the fallout? And how did this one event help to topple one of history's most infamous gangsters?
Stick with us as we explore these questions and more on history's greatest crimes.
Michael:Before we dive into the St.
Valentine's Day massacre, we need to understand Chicago's unique history, how it transformed from a frontier town into a booming metropolis by the early 20th century. This backdrop is key to understanding the forces that created both the city's growing opportunities and its dark underbelly.
Alana: illion people, was founded in: The city grew rapidly, and by: Michael:But then disaster struck.
Alana:What happened?
Michael: In: Alana:That must have been devastating for the people who had built their whole lives in the city.
Michael:And that's absolutely true. It was a catastrophe worth over $3.5 billion in today's money. But instead of destroying the city, it became A turning point.
After the fire, Chicago rebuilt itself Bigger, taller, and more ambitious than before. The city became a symbol of American resilience, known for its skyscrapers, industrial might, and booming population.
And by the end of the: Alana:It's such a fascinating story about the city of Chicago, but what I think makes that story even more interesting was the concurrent influx of immigrants to the city. They were very much a part of rebuilding the city.
From the: of work and a better life. By: Between:They settled in ethnic neighborhoods, creating vibrant communities with their own languages, traditions and businesses.
Michael:But these people came with dreams of success. Their neighborhoods were also marked by poverty and overcrowding. Many immigrants lived in tenements.
ities and the government. The:That decade also included the Johnson Reed act, an immigration act which severely limited arrivals from southern and eastern Europe.
The targeting of specific immigrant groups by domestic terrorist groups and through legal policy created deep ethnic and racial divisions in the city.
Alana:And in this environment, organized crime found fertile ground. Gangs often started as neighborhood protection groups, filling a void where the law failed to serve them.
But over time, these groups evolved into powerful criminal organizations.
Michael: th Amendment passed in:But Prohibition wasn't just about banning alcohol. It was part of a larger push to shape a, quote, better society through reform. This was the Progressive era.
Alana:That's right, Michael.
The Progressive era was a time when reformers, many of whom were middle class women, worked together to end societal problems that they believed prevented the poor and disadvantaged from leading successful moral lives. One of the main societal problems that reformers focused on was alcoholism.
They argued that the common Frequent consumption of alcohol among Americans led to alcoholism, which in turn led to the abandonment and neglect of one's family, impoverishment, disease and other moral crimes like prostitution and stealing. Progressives believed in the power of reform to improve society through government intervention.
Like laws and policies, they championed ideas like public health, education, labor rights, and used strong government intervention to address the problems created by industrialization and urbanization.
Michael:But while the goals of the Progressive era sound positive, inclusive, even in reality, the not everyone immediately accepted the growing presence of immigrants.
Many native born Americans, particularly those of Anglo Saxon Protestant backgrounds, viewed these new immigrants with suspicion, derision and even prejudice. They worried that immigrants were undermining American values and traditions and preventing progress within society.
Alana:And despite the positive nature of progressive reforms, many reformers took a rather paternalistic approach to immigrants. Reformers often viewed immigrant communities as chaotic and unruly and in need of discipline and moral uplift.
They saw alcohol as a symbol of everything that was wrong with urban life. Poverty, violence and vice. All of these things they believed immigrants suffered from because of their customs and religious practices.
For progressive reformers, Prohibition wasn't just about banning alcohol then. It was about reshaping society, literally reshaping immigrants into their ideal American.
Michael:So at the turn of the century, Prohibition became a cornerstone of the progressive movement.
Organizations like the Anti Saloon League and the Women's Christian Temperance Union argued that alcohol was the root cause of the current social ills and that banning it would lead to a healthier life for families, safer communities and a more productive workforce.
Alana:But for many immigrant communities, Prohibition felt like an attack on their identity. Drinking was often woven into cultural traditions, celebrations, religious ceremonies and social gatherings.
The saloon then, as much then as it is today, wasn't just a place to drink. It was a community hub where people gathered to share news, find jobs, and connect with others.
Michael:Prohibition also highlighted a deep divide between rural and urban America. In rural areas where progressive ideals often aligned with conservative religious values, banning alcohol just made sense.
But in cities where immigrant cultures thrived, it felt like a moral crusade imposed by outsiders.
Alana:This cultural divide fueled resentment.
Immigrants and working class Americans saw Prohibition as an effort by elites to control their behavior and erase their traditions, culture and ethnic identities. And they weren't wrong. Many Prohibition advocates explicitly linked their cause to the Americanization of immigrant groups.
Michael: n went into effect in January:Gangsters like Al Capone, who himself came from an immigrant background, filled the void left by legal alcohol. They supplied the speakeasies with liquor.
They bribed the authorities to look the other way and built criminal empires on the backs of a law that many Americans simply didn't respect.
Alana:So while prohibition was rooted in progressive ideals, its enforcement created the perfect environment for organized crime to thrive. And in Chicago, it led to a bloody battle for control between men like Al Capone and Bugs Moran.
Michael:Let's now take a look at how Prohibition fueled these rivalries and set the stage for the St. Valentine's Day Massacre.
Alana: th Amendment in:Just as an aside, here I find the significance of bootlegging to American history really interesting. Michael, would you tell our listeners more about who they were?
Michael:Oh, I would love to. A bootlegger was someone who illegally manufactured, transported, or sold alcohol.
But the term itself dates back to the 19th century when smugglers would hide flasks in their boots. But during prohibition, bootlegging became so much more alcohol creation and transportation on an industrial scale.
Alana:That's right, Michael.
In the southern parts of the nation, bootleggers making and shipping homemade moonshine began to use souped up cars to stay ahead of the local police and federal agents. And that would ultimately lead to the development of stock car racing and specifically nascar.
But over in Chicago, in the mid east, bootleggers didn't just smuggle alcohol, they built empires. They imported liquor from Canada, made moonshine and hidden distilleries galleries, and bribed law enforcement to look the other way.
They supplied the thousands of illegal bars known as speakeasies, where people could drink, dance, and socialize away from the prying eyes of the law.
Michael:And in Chicago, no bootlegger was more notorious than Al Capone. So Al Capone didn't invent the trade, but he damn near perfected it. Capone wasn't just selling alcohol. He was building a criminal enterprise.
He controlled the distribution networks. He bribed the officials and eliminated rivals with ruthless, violent efficiency. And he did it with a smile on his face.
Alana:But Capone wasn't alone. Chicago's entire political and law enforcement system was deeply corrupt.
The city's political machine, led by figures like mayor William Big Bill Thompson, was notorious for its patronage system. Politicians and police officers were often on the payroll of gangsters, turning a blind eye to their activities and violence.
Michael:This corruption created a sense of lawlessness for many working class Chicagoans. Gangsters like Capone were Seen as folk heroes, people who defied the system and provided jobs and money and even charity to their communities.
Alana:But this wasn't just about survival. Organized crime thrived on violence. Rivalries between gangs were common to control aspects of trade or other areas of influence.
rol over alcohol. By the late: Michael:And that's the backdrop for the St. Valentine's Day Massacre. It wasn't just a violent crime, it certainly was that.
But it was the culmination of decades of city growth, large scale immigration, political corruption and gang violence that defined Chicago in the early 20th century.
Alana: orward into the decade of the:After the devastation of World War I, America was booming.
The economy was growing at an unprecedented rate, and new mass produced technologies like the automobile, the radio and motion pictures were revolutionizing daily life.
Michael:At the same time, urbanization was reshaping the entire country. For the first time in American history, more people lived in cities than in rural areas.
Cities like Chicago became hubs of innovation, culture and opportunity. But as we've also discussed, they became places of stark inequality and growing ethnic tensions.
Alana: Culturally, the:Younger generations embraced a more carefree, consumer driven lifestyle that sometimes appalled their parents.
Michael:This cultural clash wasn't just about fashion or music. It was about power.
Groups like the Ku Klux Klan gained influence by promoting a return to quote traditional values, while large immigrant communities and urban youth pushed for progress and acceptance.
Alana: ort of alcohol, was passed in:It was supposed to solve social problems, curb crime, and create a more moral society.
Michael: But by the:But for men like Capone and Moran, Prohibition was the foundation of their power and they were willing to kill to protect it.
Alana: The:But these organizations had already laid the groundwork through other criminal enterprises, like gambling, extortion, and prostitution. And that made it all the easier for them to turn to supplying illegal alcohol to those with the cash to pay for it.
Michael:The criminal organizations of the time were highly structured, almost like corporations. At the top were the bosses, men like Capone and Moran, who made the big decisions and reaped the largest profits.
Beneath them were lieutenants who managed different aspects of the business, from smuggling routes to protection rackets.
Alana: th organized crime during the:For them, loyalty was everything, and betrayal often meant death.
Michael:But it's a tale as old as time. The structure of these organizations wasn't just about efficiency. It was about control and greed.
Keeping the organization tightly managed, crime bosses could expand their operations across entire cities, controlling neighborhoods, industries, and even local governments.
Alana:And to make it all the more complex, it wasn't just traditional criminals who enjoyed the trade of illegal alcohol supplied by organized crime. Speakeasies, for example, became cultural hubs where people from all walks of life came together to drink, dance, and socialize.
Many of these establishments were owned or supplied by crime syndicates.
Michael:At the same time, these organizations wielded enormous political power. They controlled elections. They told people who they should vote for. They bribed the officials and even shaped city policies.
In cities like Chicago, the very lines between legal and illegal worlds were often very blurred.
Alana:And as we've explained before, for many working class families, organized crime also provided a sense of stability, at least on the surface. Gangsters offered jobs, protection, and even charity in their communities. But this came with a cost.
Violence, fear, and the constant threat of retribution. And in Chicago, that violence came to a head due to the rivalry between gang leaders Al Capone and Bugs Moran.
Let's take a closer look at how these two men and their gangs came to dominate the city.
Michael:To fully understand the St. Valentine's Day massacre, we really do need to know more about the two men at the center of it. Al Capone and Bugs Moran.
ding up to that bloody day in: Alana: orn in Brooklyn, New York, in:His parents were working class, his father a barber and his mother a seamstress.
Michael:Capone's early life was marked by a mix of ambition and trouble. He was a bright student, but his temper often got him into fights.
He eventually dropped out of school and found odd jobs while also being a part of many different youth street gangs.
Alana:By the time he was a teenager, Capone was already drawn into the world of organized crime. He started as a member of small time street gangs in Brooklyn, where he learned the ropes of the criminal underworld.
His big break came when he joined the gentleman gangster Johnny Torrio's organization. Torrio, who had immigrated from southern Italy as a boy, had found success as the leader of the infamous Five Points gang in Manhattan.
For some time, he was commonly known as the biggest gangster in America. And as one US Official put it, Torrio was, quote, the smartest and I dare say the best of all hoodlums. Best referring to talent, not morals.
End quote.
Michael:Torrio served as a mentor to the young Al Capone. And when Torrio decided to expand his criminal organization to Chicago, Capone went with him.
Almost as soon as prohibition began, the windy city of Chicago had offered an excellent opportunity to gangsters for bootle legging. And in Chicago, Capone quickly rose through the ranks to become known for his charisma and ruthlessness.
Alana: By the mid-: t his gangster career, and by:It's Europe for me. End quote. Now, just one interesting fact.
rio left the United States in: Michael: oggling number, Elena. In the:And Capone wasn't just a gangster. He was also a public figure known for flaunting his expensive suits, his flashy lifestyle, and that Al Capone smile.
But Capone's success came at a cost. His empire was built on escalating violence. He eliminated rivals with brutal efficiency.
And his name became synonymous with the bloody gang wars of the prohibition era.
Alana: s Moran. Born In Minnesota in:He was actually born Adelar Kunin to a French immigrant father and a mother of Canadian descent.
Michael:That's right, Elena. So Bugs Moran was also connected to the wave of immigration that we've been talking about. Moran's early life was marked by rebellion.
He dropped out of school as a teenager and quickly turned to crime. In his early 20s he fled to Chicago to avoid his crimes back home. But almost immediately he was back to his old ways.
He was caught trying to rob a warehouse, taking part in a horse stealing ring, even taking part in a robbery involving the death of a police officer. He robbed a freight car for which he actually received a variety of prison and jail sentences for all of these things.
That is when young Adelard Coonin first adopted the name George Moran. It was the first name he thought of when police asked him who he was.
George Moran was a violent and unstable man who got the name Bugs because everyone thought he was nuts or buggy.
Alana:In Chicago, Moran joined the Northside Gang, a predominantly Irish organization led by Dean o' Banion. Moran's reputation as a hothead and a fighter made him a key figure in the gang's operations.
In:When o' Banion was killed, Moran became a prime leader of the north side gang. And he was determined to take revenge on Capone and his south side gang, escalating the violence in Chicago's streets.
Moran's constant targeting of Torrio is actually what encouraged him to leave Chicago for a little for Italy, allowing Capone to take over.
Michael:Unlike Capone, Moran wasn't known for his charisma or strategic thinking. He was more of just a brawler, a man who relied on brute force rather than finesse. The rivalry between Capone and Moran was intense.
These two men were arch enemies when it came to the business competition and and ideas of revenge. But in reality they were two sides of the same coin.
Capone the flashy and calculated Italian American mob boss and Moran the hot headed Irish American gang leader.
Alana: Throughout the: he real turning point came in:And this drive by shooting sent over a thousand bullets into the building, killing several people, but actually missing their main target.
Michael: and failed to kill Capone in: Alana: ,:They think they're there for a routine meeting, possibly a bootlegging deal.
Michael:Instead, two men dressed as police officers walk in, followed by two others in civilian clothes. The gang members are ordered to line up against the wall. They think it's a raid, but it's actually a setup.
Alana:What happens next will go down as one of the most brutal crimes in American history. Stay with us.
Michael: Foreign: Alana:Unbeknownst to them, this wasn't going to be a routine business meeting. Outside, two men dressed as police officers and two others in civilian clothes approached the building.
They planned every detail to make it look like a police raid.
Michael:The fake cops entered first, guns drawn. They ordered Moran's men to line up against the wall as if they were going to be arrested.
Thinking that this was just a standard raid, the men complied. They knew how this worked. They would comply and then pay some bribes to fix this misunderstanding.
Alana:But this was no arrest. Moments later, the other two men walked in carrying Thompson machine submachine guns. Known colloquially as tommy guns.
ese guns could pump out up to:And as a result, in Chicago, Tommy guns actually had another name, the Chicago typewriters for the click, click, click sounds that they made as bullets were fired.
What's interesting is that these guns had originally been manufactured to help American forces break the stalemate of trench warfare and win World War I for the Allies.
After World War I ended in: Michael: th of:Or so they thought. The scene was chaotic. Blood pooling on the floor, walls riddled with bullets, and the echoes of gunfire still ringing in the morning air.
Alana:When the dust settled, six of the men were dead. The seventh, Frank Gusenberg, was critically wounded, but still clinging to life.
He was rushed to the hospital, but even as he lay dying, he refused to identify his killers.
Michael:When asked who shot him, Gusenberg replied, quote, no one. Nobody shot me. That's the code of silence these men lived and died by.
It also highlights the distrust of the government and police authorities, as well as the loyalty, even in death, that the mob underworld worked in.
Alana:Meanwhile, the fake police and their accomplices made a clean getaway.
Witnesses later reported seeing the men leaving the garage calmly, even loading their weapons into a car, as if they were just wrapping up a routine police operation.
Michael:When the real police arrived, they were met with one of the grisliest crime scenes in history. Photos of the massacre spread quickly, shocking the nation. But here's the thing. The intended target, Bugs Moran, he wasn't even there.
Alana:That's right. Moran had been running late that morning when he saw the fake police outside the garage. He turned around and avoided the massacre altogether.
But even though Moran lived, the loss was devastating for his organization. The seven victims included high ranking members of Moran's gang.
Michael:So who was really behind the St. Valentine's Day Massacre? Well, the obvious suspect, of course, was Al Capone.
And it was common knowledge that he was the undisputed king of Chicago south side, and one of the most powerful mob bosses in the country. But proving his role in the massacre was another story altogether.
Alana:Capone had both the motive and the means. The massacre wiped out key members of Bugs Moran's north side gang, Giving Capone greater control over Chicago's lucrative bootlegging trade.
But there's a catch. Capone wasn't even in Chicago that day.
Michael: ,:But let's be real, right? Capone didn't really need to be there personally. He had plenty of men who would carry out the job for him.
Alana:And one of those men might have been Fred Killer Burke, A known associate of Capone's who was skilled in using the same weapons that were used in the massacre. Burke's fingerprints were later found on a tommy gun in his possession, linking him to the crime. But that wasn't enough to convict him.
Years later, other criminals would implicate him in the crime. But in the end, no one was convicted for the St. Valentine's Day massacre.
Michael: . Valentine's Day Massacre of: Alana:I agree. And the lack of a conviction means that we'll never really know all of the details.
There's another theory that the massacre was actually a setup to frame Capone. Some believe that rival gangs or even corrupt law enforcement or orchestrated the attack to turn public opinion against him.
After all, the massacre brought so much heat on Capone that it marked the beginning of the end for his empire. Another possibility is that it was an inside job.
Some accounts suggest that someone within Moran's own gang may have tipped off Capone's men either out of fear or for personal gang because, you know, gang loyalty wasn't exactly ironclad.
Michael:And let's not forget Bugs Moran himself. While he was clearly the target, was his survival entirely coincidental?
Or could he have known about the hint and even set his men into the trap to save his own skin?
Alana:While there's no hard evidence to support that the murkiness of the world of organized crime meant that anything was a possibility, what we do know is that the massacre achieved its goal of crippling Moran's gang, but it came with a cost.
Michael: . Valentine's Day massacre of:But it also had unintended consequences for Al Capone himself, who many believe was behind the attack. The massacre drew so much attention that it became impossible for authorities and the public to ignore the violence continuing to grip Chicago.
And more to the point, it represented a turning point in America's war on organized crime.
Alana:Coming up, we'll look at how this one event helped take down Al Capone and change the course of American history.
Michael:So News of the St. Valentine's Day Massacre spread rapidly in the following days.
Newspapers across the country published graphic photos of the crime scene, and the public outcry was deafening. And in short, the massacre created a public relations nightmare for Capone.
Alana:It also caught the attention of federal authorities, specifically newly elected President Herbert Hoover, who immediately looked for a way to bring Capone and gangsters like him down. But they couldn't pin the massacre on him. And in reality, they didn't care what crime actually brought an end to his illegal activities.
So Hoover began adding more money and agents to the effort to end organized crime, and specifically Al Capone's Organized crime instead of murder or alcohol, bringing down Capone. In the end, it was not paying his taxes. Capone was arrested on charges of tax evasion.
Michael:That's right, tax evasion. Capone's lifestyle was lavish, and it didn't exactly match his reported tax income.
By: Alana:And what about Bugs Moran? We know the massacre effectively destroyed his gang, but he managed to survive. What happened to him?
Michael: financial crimes as well. In: When he emerged in the: Alana: one and went back to Italy in: Michael:Yes. He said he was through with organized crime.
Alana:That turned out not to be completely true. When Torrio went back to Italy, he started meddling in organized crime again.
A few Years later, in:As a result, Torrio returned to the United States. As you remember, the federal authorities often focused on financial crimes to successfully convict monsters.
And similarly, in: Michael:Why can't mobsters just pay their taxes now? As we mentioned, no one was convicted for their part in the St. Valentine's Day Massacre.
But despite that, the event had a huge impact on policy and encouraged some major historical shifts. First and foremost, it underscored the failure of Prohibition as a policy.
The 18th amendment was rooted in progressive ideals that banning alcohol would solve societal problems. But instead, it created a thriving black market that enriched criminals like Al Capone and heightened criminal activity.
It had really the opposite effect.
Alana:It all seems to point to a powerful lesson about the limits of moral legislation. When a law is wildly unpopular and difficult to enforce, it often creates more problems than it solves. Prohibition didn't eliminate alcohol.
It made it more dangerous, drove it underground and empowered organized crime and criminals while eroding trust in law enforcement and.
Michael:As images of the St.
splashed across newspapers in: By the early: Alana:The massacre also highlights the corrosive impact of corruption. In Chicago, organized crime thrived not just because of violence, but because it had infiltrated the political and law enforcement system systems.
Judges, police and politicians were often complicit, either through bribery or fear.
Michael:And this kind of corruption creates a sense of lawlessness that undermines the very institutions meant to protect society. When the public sees the laws being ignored or manipulated by those in power, it breeds cynicism and distrust.
Alana:And culturally, the St. Valentine's Day massacre remains one of the most infamous crimes in American history.
It's been immortalized in books, films and TV shows, often as a symbol of the brutality and excess of the Prohibition era. And the figures of Al Capone and Bugs Moran are often glamorized and romanticized as larger than life anti heroes.
Michael:And part of that originates in the broader social, economic, and cultural forces that drove the massacre in the first place.
The poverty and official and unofficial discrimination that many immigrants faced created a need for a special protection and opportunities from within. Those special protection and opportunities often evolved into and from organized crime.
Alana:And that same organized crime thrived within and exploited the moral boundaries that progressive reformers had hoped would fix the sins of society.
Reformers of the progressive age had hoped that by making alcohol, gambling and prostitution illegal, it would help the poor avoid their vices and improve their standing in society. But reality turned out to be quite different.
Michael:But while the St. Valentine's Day massacre mostly stood as a negative symbol of the Roaring Twenties, it did have a few positive consequences.
The massacre revealed the need to reform law enforcement systems to help combat corruption from within. And in the process, it also led to a more coordinated federal approach to combat organized crime, including the creation of agencies like the FBI.
Alana:In addition, Chicago became the first city with an independent forensic crime laboratory at Northwestern University. The lab was initially established in an effort to find the murderers. So in some ways, the field of forensic science was born out of this tragedy.
Michael:Looking back, the St. Valentine's Day massacre was clearly an infamous crime in history. But it also offers lessons that are still relevant today.
Whether it's about creating effective laws, addressing systemic corruption, or understanding the root causes of violence. History has so much to teach us.
Alana:And perhaps the most important lesson is this. When society tries to impose simple solutions on complex problems, the consequences can be far reaching and unexpected.
It's a reminder that history is always more complicated than it seems.
Michael:That's all for now. This has been history's greatest crimes. I'm Michael.
Alana:And I'm Alana. Stay curious.
