Al Capone and the Valentine's Day Massacre

Summary

---

After Dark: Myths, Misdeeds & the Paranormal

Episode Summary: Al Capone and the Valentine's Day Massacre

Release Date: February 5, 2026
Host(s): Anthony Delaney, Maddie Pelling
Guest: Jonathan Eig (Pulitzer Prize-winning author of "Get Capone: The Secret Plot That Captured America's Most Wanted Gangster")

---

Overview

This episode delves into one of the darkest and most notorious events of Prohibition-era America: the St. Valentine’s Day Massacre. Hosts Anthony and Maddie, joined by eminent historian Jonathan Eig, dissect the conditions that birthed gangland Chicago, the personalities at its heart—most notably Al Capone—and the enduring mythos and consequences of the massacre. They explore how the event became national news, the ambiguity that still surrounds its perpetrators, and its pivotal role in shaping policy and popular culture in the years that followed.

---

Key Discussion Points & Insights

1. Setting the Scene: Prohibition and Chicago’s Criminal Underworld

[01:22–05:45]

• Prohibition’s Unintended Consequences:
  • The 1920 ban on the sale and distribution of alcohol in the U.S. quickly led to a lucrative black market, as people refused to give up drinking.
  • "Almost immediately, the rule was flouted. People did not want to give up their booze... the government never had a plan for enforcing Prohibition." – Jonathan Eig [05:45]
• Rise of Organised Crime:
  • Criminals saw opportunity, shifting from existing vice trades to bootlegging.
  • Fierce competition and huge profits led to violent clashes among rival gangs.

2. Chicago’s Gangs & Their Leaders

[08:06–14:55]

• Al Capone and His Rivals:
  • Capone—celebrity, feared leader—embodied Prohibition-era gangsterism.
  • Notable rivals included George "Bugs" Moran of the Northside Gang and "Machine Gun" McGurn.
• Ethnic Dynamics:
  • Gangs often aligned along ethnic lines (Irish, Italian, Jewish), mirroring Chicago’s immigrant makeup.
  • "There is a lot of ethnic influence... Capone's gang was actually fairly non-denominational." – Jonathan Eig [14:55]
• Media’s Role in Myth-Making:
  • Nicknames like "Scarface" and "Machine Gun" amplified the drama, often crafted by and for the press.
  • The violence and spectacle became both local entertainment and a tourist draw.

3. Corruption and Law Enforcement

[10:00–11:42; 23:21–24:24]

• Symbiotic Relationship:
  • Gangsters routinely bribed police, prosecutors, and judges; underfunded law enforcement proved easy to corrupt.
  • "The cops were in Capone's pocket... the only real concern was your rivals." – Jonathan Eig [10:24]
• Blurring Lines:
  • Gangs often operated with impunity, aided by compromised officials and, possibly, by the active involvement of police in key crimes.

4. The Massacre: What Happened on February 14, 1929?

[17:44–22:31]

• The Lure and The Setup:
  • Capone's men allegedly set up a fake whiskey delivery to draw rival Northsiders to a garage.
  • Precise details and ultimate mastermind remain unclear to this day.
• The Execution:
  • “Seven men were in that garage early on Valentine's Day morning waiting for somebody.” – Jonathan Eig [18:10]
  • Killers, some dressed as police, lined up the men and executed them with machine guns.
• Eyewitness Testimony:
  • One severely wounded survivor told investigating officers: “This was the cops who did it. I'm not going to talk to you.” [19:27]

5. The Impact and Fallout

[22:31–28:59]

• Lasting Shock and Media Sensation:
  • Grisly photos published in tabloids shocked Americans; the event’s visibility set it apart from other gangland killings.
  • "Part of it is because of the media... Americans are waking up to pictures of the Valentine's Day massacre the likes of which they have never before seen." – Jonathan Eig [21:06]
• Public Outcry and Political Ramifications:
  • National outrage fueled by media coverage led to calls for a crackdown on organized crime.
  • President Herbert Hoover became obsessed with “getting Capone” for symbolic reasons, regardless of direct evidence tying him to the massacre.

6. Gun Culture and Policing

[28:59–29:34]

• Rise of Machine Guns:
  • Firearms designed for World War I flooded the streets, escalating violence.
  • "You can buy them anywhere... it's escalating the violence and it's making it easier for people to kill one another." – Jonathan Eig [29:34]
• No Immediate Gun Control Reforms:
  • Despite the horror, legislative change was slow and largely ineffective.

7. The Fall of Al Capone

[31:57–37:53]

• From Gangster to Public Enemy #1:
  • Unable to convict Capone for violent crimes, authorities built a case for tax evasion, a novel approach legitimized by recent Supreme Court rulings.
  • "Ultimately, they make the practical decision that it's better just to put him behind bars any way we can..." – Jonathan Eig [32:24]
• Capone’s Downfall – A Mixed Public Reaction:
  • Many saw him as a folk hero who provided what people wanted; juror bias against the IRS and sympathy for Capone were real concerns for prosecutors.
  • His trial was irregular, with a jury swap to ensure a conviction, after which Capone was sentenced to 13 years—the stiffest ever for tax evasion—and sent to Alcatraz.

8. Capone’s Final Years

[37:53–39:20]

• Only in his 30s when imprisoned, Capone’s health rapidly declined due to neurosyphilis.
• After his release, he lived quietly and out of the public eye, a far cry from his former infamy.

---

Notable Quotes & Memorable Moments

• On Prohibition’s Naivety:
  • “The government really thought that everyone would volunteer to just put away, to give up, pour down the drain, their fine bottles of wine and spirits and that everything would be happy...” – Jonathan Eig [05:45]
• On Press Coverage:
  • “This was definitely entertaining... news reporters from all over the world would come to Chicago and seek interviews with Al Capone, and he would grant them because he wanted to see himself as a celebrity.” – Jonathan Eig [13:50]
• On the Massacre Itself:
  • “Some cars pull up in front of the garage. Some of the neighbors said it looked like police cars... the men had been lined up against the wall of the garage and gunned down with machine guns and rifles and left there to die.” – Jonathan Eig [19:27]
• On Murder and Media:
  • “Why did this one turn people's stomachs? Why did it ignite this drive to get Capone and put him behind bars? It’s because of those photos in many ways.” – Jonathan Eig [21:06]
• On Prosecuting Capone:
  • "Are we going to be mocked for saying the only case we can make against him is he didn’t pay his taxes?... but it’s better just to put him behind bars any way we can." – Jonathan Eig [32:24]
• On Capone's Public Image:
  • “He would say, I’m just giving people what they want. I’m doing the same thing—when they serve drinks on Park Avenue, they call it hospitality. And with me, they call it a crime.” – Jonathan Eig [35:50]

---

Key Timestamps

| Timestamp | Segment / Topic | |-----------|---------------------------------------------------| | 01:22 | Atmospheric introduction to massacre and Prohibition Chicago | | 05:45 | Prohibition’s social and criminal consequences | | 08:06 | Violent gang rivalries, emergence of Capone | | 10:24 | Police corruption and inability to curb gang power| | 12:21 | Gang nicknames, media mythologizing crime | | 14:55 | Ethnic backgrounds shaping gang formations | | 17:44 | The massacre: set-up and confusion over planners | | 19:27 | Massacre details, survivor testimony | | 21:06 | Media’s new gruesome coverage shifts public perception | | 23:21 | Discussion on police (possible) involvement | | 25:01 | Aftermath: lack of leads, Hoover’s obsession | | 27:58 | Prohibition repeal; political angle | | 29:34 | Gun availability and rise in weapon lethality | | 31:57 | Capone’s arrest and prosecution for tax evasion | | 35:50 | Mixed public reaction to Capone’s conviction | | 37:53 | Capone’s demise and post-prison obscurity |

---

Tone and Style

The episode maintains a conversational, engaging tone with darkly cinematic flair—balancing sharp historical analysis with the grim drama of true crime. Jonathan Eig’s measured expertise is complemented by Maddie and Anthony’s quippy rapport and fascination with the period’s spectacle and moral ambiguity.

---

For Listeners Wanting More

Jonathan Eig’s work, especially "Get Capone," is referenced throughout and recommended for those seeking a deeper exploration of Prohibition Chicago. He also mentions a forthcoming biography of George Soros ([40:01]).

---

This episode is essential listening for anyone fascinated by the cross-section of American crime, politics, media, and legend-making. It not only examines the anatomy of one shocking event, but also how its myth and aftermath reverberate nearly a century later.

Transcript

[Boost Mobile Representative]

Big news. Boost Mobile is now sending experts nationwide to deliver and set up customers new phones at home or work.

[Jonathan Eig]

Wait, we're going on tour?

[Boost Mobile Representative]

Not a tour. We're delivering and setting up customers phones so it's easier to upgrade.

[Jonathan Eig]

Let's get in the tour bus and hit the road.

[Boost Mobile Representative]

No, not a tour bus. It's a regular car we use to deliver and set up customers phones at home or work.

[Jonathan Eig]

Are you a groupie on this tour?

[Boost Mobile Representative]

We deliver and set up phones. It's not a tour.

[Jonathan Eig]

Oh, you're definitely a groupie.

[Boost Mobile Representative]

Introducing store to door switch and get a new device with expert setup and delivery wherever you're at.

[Jonathan Eig]

Delivery available for select devices [e-mail] Boost.

[Boost Mobile Representative]

Mobile is now sending experts nationwide to deliver and set up customers new phones.

[Jonathan Eig]

Wait, we're going on tour?

[Boost Mobile Representative]

We're delivering and setting up customers phones. It's not a tour.

[Anthony]

Not with that attitude.

[Boost Mobile Representative]

Introducing store to door switch and get a new device with expert setup and delivery.

[Jonathan Eig]

Delivery available for select devices [e-mail] the.

[Boost Mobile Advertiser]

Longer you stay alive, the longer you can enjoy Boost Mobile's unlimited plan with a price that never goes up. So here are some tips. Do not parallel park on a cliff if you want to enjoy an unlimited plan with a price that never goes up. Do not mistake a wasp nest for a pinata if you want to enjoy an unlimited plan with a price that never goes up. Do not microwave a hard boiled egg if you want to enjoy an unlimited plan with the price that never goes up. Stay alive and enjoy Unlimited Wireless for $25 a month. Forever with Boost Mobile. After 30 gigs, customers may experience lower speeds. Customers will pay $25 a month as long as they remain active on the Boost Mobile unlimited plan.

[Anthony]

Morning creeps over Chicago on Valentine's Day 1929. Settling on a city worn thin by years of gang wars, bombings, ambushes, Prohibition. Deals that kept the streets simmering. At the Clark street garage, the Northside men think today is routine. Another shipment of hijacked whiskey. Another gamble in a war that never quite ends. They warm their hands, trade jokes, never guessing. This morning has been chosen for something far darker. Outside, engines idle. The footsteps approach. The silhouettes in the doorway look like police. Too calm, too controlled. And as the first Tommy Gunn rises into view, the truth becomes clear. This will be a massacre for the age. Tommy guns, fake police uniforms. A city drowning in bootleg liquor and gangland wars. And seven bod left on a cold garage floor. These are the beats of the St. Valentine's Day Massacre. Now in this episode, we step back into Prohibition era Chicago, where a ban on alcohol birthed violent bootleggers, rival mobs carved the city into battlefields and corruption seeped so deep that killers could masquerade as cops and vanish into daylight. From our modern perspective, it feels almost cinematic, but the terror and the bullets were all too real and the message was unmistakable. Power ruled, law didn't. From Prohibition era Chicago, this is After Dark.

[Maddie]

Hello, everyone, and welcome to After Dark. I'm Maddie.

[Anthony]

And I'm Anthony.

[Maddie]

Now on After Dark. We are never usually ones for sentimentality, and this week is no different. While some bring flowers and chocolates, we are bringing you the latest analysis of various horrifying events of the past, because that's just how it is. Okay, now with that in mind, what better historical event to explore than the St. Valentine's Day massacre of 1929? We're in Chicago, so think Prohibition era bootlegging, crooked cops, Tommy machine guns, and of course, Al Capone. Guiding us through this oftentimes dangerous world is Jonathan Eig, the Pulitzer Prize winning author of many fantastic books, including Relevant for our conversation today. Get Capone. The secret plot that captured America's most wanted gangster. Jonathan, welcome to After Dark.

[Jonathan Eig]

Thanks for having me.

[Maddie]

We're really excited to have you.

[Anthony]

I think you're our first Pulitzer Prize winner, Jonathan. So you're ahead of the pack already.

[Jonathan Eig]

Oh, it's an honor. Thank you.

[Anthony]

Before we get into the chat, I just want to give this story in a nutshell so that people have an overview and then we'll get into the details. So we are Talking about the St. Valentine's Day Massacre, which was the brutal murder in 1929 of seven members of Chicago's Northside gang by rivals widely believed to be Capone's south side gang during Prohibition. Now we will find people posing as police officers, assailants lined up the victims against a garage wall and executed them with machine guns, shocking the nation even within this gangland warfare and highlighting the problems that were infused within Chicago society through gang violence, though no one was ever actually convicted and it became a symbol of mob brutality. Now, with that basic overview, let's chat to Jonathan about the ins and outs and the details. More specifically, Jonathan, can you give us an idea for those who may be less aware of this history? We don't know it as well this side of the Atlantic. What is happening in America more generally at this point and how does it lead to this gang warfare?

[Jonathan Eig]

You guys did a great job summarizing it. I'll try to Expand on that a little bit. What you have to try to imagine is that for the better part of a decade now, drinking alcohol has been made very difficult. It's illegal to buy and sell alcohol except for medicinal purposes or for religious purposes. And this has been going on for a long time. And almost immediately, the rule was flouted. People did not want to give up their booze. The government really thought that everyone would volunteer to just put away, to give up, pour down the drain, there are fine bottles of wine and spirits and that everything would be happy, we'd be a much happier and healthier country. But that never happen. And the government never had a plan for enforcing prohibition, as this law was called. It was really thought of as something that would just make everybody calmer and less violent and healthier. And when that didn't happen, the government had no backup plan. And immediately, almost immediately, people began subverting the law. People realized that this massive industry was out there for the taking. And who is best positioned to supply booze when it's illegal? Well, people who were already criminals. So you have these gang members, people who were involved in running casinos or houses of prostitution. Suddenly they get the idea that they can go into the booze business and make a fortune. And very quickly it becomes incredibly lucrative. They're making more money than they ever imagined. And as a result, of course, there's going to be conflict, there are going to be rivalries, there are going to be fights over turf. Hey, I'm supplying booze to this neighborhood. Stay out. And that's where the shooting begins. That's where the gangs decide that these profits that they're making, these enormous profits are worth fighting for. And Al Capone becomes the most famous of all the bootleggers. But every city really has its own Al Capone has a number of them, actually. And it's just that Al Capone loves publicity and carries himself with a lot of bravado that he becomes the symbol really of all of Prohibition. So by 1829, when the Valentine's Day massacre occurs, we're starting to see more of these conflicts because the profits are so great. And still government is doing nothing really to try to curb this violence and to curb this illegal selling of booze.

[Maddie]

So, Jonathan, we have this state created black market in a lot of ways, that's been born out of the oppression that comes with prohibition. And we have the gang violence that in this instance is eventually going to lead to the massacre that we're talking about. So let's talk a little bit about Chicago Gangs in particular. This is a really bloody and dangerous time, isn't it, in terms of these gang wars. So who are. You've mentioned Al Capone already, but who are some of the characters that we are maybe going to meet along the way? And how, how did people end up in this situation with these rival gangs?

[Jonathan Eig]

Well, Al Capone was not only the most famous, he was the most powerful leader in Chicago of these gangs. And they were numerous gangs, at least, you know, three or four big ones in Chicago at any time. And they, it was fluid, it was changing all the time because guys would get knocked off or they would get out of the business because they realized that they were going to get knocked off if they didn't get out of the business soon. And Capone was really kind of ambivalent about this. You know, he'd made enough money at this point that he felt like he could leave, but he was still had had so many tentacles, he had so many businesses going and, and he was in constant rivalry with in particular the north side gang where the Valentine's Day massacre occurs. But over the course of his, you know, eight or nine years, by now that Capone was really active in gangland Chicago, there were constant rivalries and usually his rivals ended up dead. And he didn't, which is why another reason that wasn't just that he was attention getting and that he was, you know, a celebrity. It was that he actually, you know, survived when the others didn't. So you have this constant series of battles, of skirmishes, and at this point, by 1929, Capone is really trying to find a way out of it. He knows that the government is starting to investigate him for his failure to pay taxes. He's worried about the heat on him. He's made enough money and he just can't get out.

[Anthony]

Isn't that very interesting that even Al Capone can't get out of this. This situation that he has, you know, somewhat contributed to himself, I suppose. Just for context, Jonathan, let's give us an idea of how these gangs, which seem to be to some extent ruling the city in certain ways, how they're coexisting alongside the police force. Because I'm imagin there is a lot of interconnection there.

[Jonathan Eig]

Yeah, that's a really important point to make. Very early on, the gangs realized that the police were not going to be very effective in trying to take them down. Remember, the police at this time were poorly paid. The starting salary for a police officer in Chicago was about the same as for a Dog catcher. So were they really going to risk their lives to take on these gangs? Well, probably not. It was almost impossible that, you know, this is a really loose knit organization. They're bringing in booze from all these different sources. There was no way the police were up to trying to control this. So when they started offering bribes to the cops and bribes to the attorneys, to the prosecutors, to the judges, it was easy pickings. They were all receptive to being bribed because they really had no, no chance of enforcing the law to begin with. So the cops were in Capone's pocket pretty much. And that's why in the course of the twenties, during the age of prohibition, despite the fact that there were dozens and dozens of murders, gangland murders, there was not a single conviction. And that's because the system was. Was completely corrupted. So the only real concern was your rivals. If you could take care of your rivals, if you could keep from being overtaken by a larger, more powerful, more dangerous gang, you were pretty much good to go.

[Maddie]

Not to confuse periods of American history, but it is like the sort of Wild west in the sense that, you know, there don't appear to be any rules or the rules are constantly being bent or broken. We've spoken about Al Capone. You know, he comes to Chicago in 1919 and takes over, eventually the Chicago outfit, the gang that he's in charge of. But we have some other characters as well that I have in my notes. And I just. I love some of the nicknames that they're given as well. So I have George Bugs Moran, who is the leader of the Northside gang. So he's one of the rivals of Al Capone, isn't he? And then also jack machine gun McGurn. I mean, he doesn't sound like a great guy off the bat. Jonathan.

[Jonathan Eig]

Well, if you're trying to improve your image, maybe Machine Gun shouldn't be the nickname that you go with.

[Anthony]

Or maybe it should, depending on what the image you're trying to build up.

[Jonathan Eig]

It suited him well. The nicknames were mostly invented by the media. And you have to remember that the newspapers were having a lot of fun and making a lot of money by writing about these guys. It was incredibly colorful. Damon Runyon built a whole career out of it. Guys and Dolls stems from this era and these kinds of charact. So this was just great ink and that helped, you know, make this story go. That's probably why we're still talking about Al Capone is because the newspapers loved him. And, you know, his nickname, of course, was Scarface, also not the most flattering. And he would actually go into the newspaper offices and complain about. About the use of the nickname. Like, you know, I have other nicknames, you know, why do you have to keep using that one? How do you think it makes my mother feel to see me called Scarface in the newspaper? So these guys, you know, they were. It was the Wild West. They. They felt like they could operate with impunity. And the nicknames were just part of the. The fun for Chicagoans who were following this, as long as they didn't get mixed up in their business.

[Maddie]

I love this idea of the. The whole city becoming a kind of theater, right? That this is a performative arena in which this drama is playing out. And yes, if you are involved in it, it might end in your death. It's incredibly dangerous. But actually, for the ordinary Chicago spectator consuming this through the media or maybe catching glimps, people, there is a sort of excitement here, right, that this is a form of cultural entertainment. Is that fair to say?

[Jonathan Eig]

It is. There were magazines on the newsstands with gory photos. People coming to Chicago on a vacation would want to pick up these magazines and these postcards to send home to say, hey, look, I visited Al Capone's Chicago. And their friends would joke with them when they got home. How many bullet holes did you get in the side of your car? This was definitely entertaining. And that's partly why these news reporters from all over the world would come to Chicago and they would seek interviews with Al Capone, and he would grant them because he saw himself or wanted to see himself as a. As a celebrity and that this was just his line of work.

[Anthony]

I'm noticing here as well, Jonathan, that there is. And this is a guess, so you'll have to enlighten me if this isn't the case, but that there seems to be a bit of a naming divide slightly. So we're talking, let's say, in terms of the north side and the south side gang here. But I'm noticing that we have the Moran surname, we have the Burke surname, we have a lot of MC surnames, and then we have Al Capone on the other side.

[Maddie]

Side.

[Anthony]

Am I noticing a kind of a pattern that's linking to immigration coming into Chicago? It sounds like there's a lot of Irish names in one side and then potentially Italian names on the other. Is that the case or is it not that clear cut?

[Jonathan Eig]

No, there is a lot of ethnic influence, and there are Jewish gangs, too. And Capone's gang was actually Fairly non denominational. He had a lot of Jews, Italians, Irishmen, all working. And it's important to think about that. One of the reasons that we see Prohibition passed in this country is because the elite think that it's a way to crack down on immigrants. And then immigrants are the ones who profit from this the most because they're the ones willing to take the greatest risks because they're, you know, they're starting out in this country and they don't have a lot of the same opportunities. Colleges aren't as accepting of their applications. They're not getting good educations. They're dropping out early to help support their families. So when an opportunity. And Capone's a great example of that, you know, one of nine children growing up in the, in poverty in Brooklyn and when opportunity doesn't come knocking, when he struggles in school because he has to take all this time off to help make money for his family and he gets an opportunity to make some real money by working with some unsavory characters, well, it's kind of a no brainer. Lifelock, how can I help?

[Maddie]

The IRS said I filed my return, but I haven't.

[LifeLock Advertiser]

One in four tax paying Americans has paid the price of identity fraud.

[Jonathan Eig]

What do I do? My refund though. I'm freaking out. Don't worry, I can fix this.

[LifeLock Advertiser]

LifeLock fixes identity theft, guaranteed. And gets your money back with up to $3 million in coverage.

[Experian Advertiser]

I'm so relieved.

[Jonathan Eig]

No problem.

[Anthony]

I'll be with you every step of the way.

[LifeLock Advertiser]

One in four was a fraud. Paying American chicken. Not anymore. Save up to 40% your first year. Visit lifelock.com Special offer terms apply hi.

[Dan Snow]

There, I'm Dan, host of Dan Snow's history podcast. I can imagine on these dark winter nights, all you want to do is curl up with a cup of tea and get lost in an amazing story. Well, I can help you with that. Twice a week I tell you the most dramatic and extraordinary stories from history with details I can guarantee you've never heard before. Feel the frostbite of that grisly failed American invasion of Canada in the dead of winter. Imagine every clash and blow at the Battle of Bosworth. Follow Eleanor of Aquitaine, one of the most powerful women in the medieval world, as she goes on crusade to the holy land with 300 handmaidens in tow.

[Anthony]

She leads her own army.

[Jonathan Eig]

Everyone goes gaga for Eleanor.

[Dan Snow]

And trace the voyage of the first Vikings as they arrive on Iceland's lonely shores. For the best historical stories to get lost in, check out Dan Snow's. History.

[Maddie]

Now, Jonathan, let's go to the events of the day itself. And we know that Capone, or at least Capone's men, set up what is essentially a dummy whiskey shipment to sort of lure this other gang in. Where does it go from there? Is this the massacre itself? I assume that this is fully planned. This isn't something that escalates throughout the day. This is almost a military operation that is set in stone from those earliest hours. Right, right.

[Jonathan Eig]

But the problem is we don't know who planned it, and we don't know exactly how it was organized or who led those men to be in that garage that day. So it's to set the scene. It's a very cold February 14th in Chicago, 1929. And early in the morning, there are seven men in this gang in this garage on Clark street on the north side of Chicago. That is one of the places that Moran's men tend to hang out. Why are these men gathered so early? Is there a plan? Is there a shipment of booze coming in? Are they getting ready to go out and do some of their own criminal activity? We don't really know to this day. There are some thoughts that they were expecting a load of booze from Canada. Some people say the Purple Gang of Detroit had arranged for them to be there. Some people say it was Egan's rats out of St. Louis. Others, of course, believe it was Capone's men. There's another theory that they were being gathered to go do a hit and that some cops may have been in on it. There are all kinds of theories. All we know for sure is that seven men were in that garage early on Valentine's Day morning waiting for somebody.

[Maddie]

It's delightfully mysterious, isn't it? And I love that there's not necessarily one particular answer. So we have these men who've assembled in the garage. They don't know what's coming to them. What happens next?

[Jonathan Eig]

Well, some cars pull up in front of the garage. Some of the neighbors said that it looked like police cars. Some of them said they saw men in police uniforms get out of the cars, go into the garage, and the next thing you know, the neighbors start to hear gunshots. And it turns out that the men had been lined up against the wall of the garage and gunned down with machine guns and rifles and left there to die. And the men who committed this crime then got back in those cars and drove off. And there was only one man still alive by the time police got there. And supposedly, when the cops tried to Talk to him. He said, get, get, get lost. This was the cops who did it. I'm not going to talk to you. And he died soon after at the hospital. So there was, there were very few witnesses who were able to provide any, any more detail beyond that.

[Anthony]

One of the, the things that is. Well, there's two things actually that visually stick with me when I think about this particular incident. The first being that the, the gang members that were shot, eventually, before they were shot, they were lined up, as I understand it, facing the wall. And, and then there was from behind them, this onslaught of bullets that, you know, it was very much execution style, although they will not necessarily, or some people think they will not necessarily have known that that was coming in, that was about to happen. But then, Jonathan, there is, of course, the imagery that comes from that day because the press were over it quite quickly. And there are images that are, you know, you can find very freely on the Internet even today that are quite gruesome. And these stick with people across the United States, don't they?

[Jonathan Eig]

This is a very important point. And why are we still talking about the Valentine's Day mass massacre almost 100 years later? And part of it is because of the media. And the media was changing at that time. As I said, this was a big story. Reporters loved it, it sold papers. But we're also beginning to see the rise of the tabloid in American news with big pictures and more gruesome pictures than would have been palatable a decade earlier in the American media. You know, there was some sensitivity about publishing violent photos in the American media until the tabloid era. So suddenly Americans are waking up to pictures of the Valentine's Day massacre the likes of which they have never before seen over their, you know, oatmeal and coffee at the breakfast table. And this shocks people in a way that, you know, we can imagine today because we now have, you know, cell phone videos of criminal incidents that we would never have seen before. Now the American public, the world, shares images of events, of gruesome events as they're happening with no filters. And that's a little bit how it felt when the Valentine's Day massacre occurred. People were shocked because you might ask yourself, there were hundreds of gang led killings in America all the time. Why did this one turn people's stomach? Why did it change American history? Why did it ignite this drive to get Capone and put him behind bars? It's because of those photos in many ways.

[Maddie]

So the visibility of the violence, I suppose, is what tips this over the edge Jonathan, I'm interested in the fact that the police are maybe involved in this, or at least whoever is doing the killing is dressed. You know, they're disguising themselves potentially as part of the police force. And we know that Moran, the gang leader, sees the police car as he's approaching the garage and he actually turns away. And I think he survives this incident, doesn't he? So in your opinion, you spent a lot of time with this material and obviously written the book. Do you see the police, as you've mentioned, the sort of corruption of the police and their involvement with, you know, within these gang networks and maybe the bribes that they're taking? Do you see the police as being involved in this particular incident? Is this simply a situation in which gang members are dressing up and disguising themselves as policemen? What exactly is your opinion of what's happened here?

[Jonathan Eig]

Well, once again, we don't know. So I'm going to start by saying that I have no, I'm not going to solve this crime for you today. But I do think that in some way the police involvement seems likely. It could just be that the police loaned their cars and their uniforms to some guys. It also could just be that the police knew who did this and were paid to not investigate, to not look very hard at what happened. There's one theory that is hardly bulletproof, no pun intended, that this was done in retaliation for the death of a police officer's son. And the police officer whose son was killed by some of the guys in that garage may have helped to arrange for this assassination, made police cars available, made police uniforms available, and then made sure that the investigation wouldn't go too far. So there are all kinds of theories involved. But, you know, the fact that we have one eyewitness who survived for a little while, who said the coppers did it, makes us think that there's some. There could have been some involvement from the police, but this is all highly uncertain.

[Anthony]

But what we do know is that to a certain extent, in certain quarters, there is definitely an outcry for some form of solving of this particular ambush, this particular crime to take place. People, as we've said, are very in tune with what's happened because of the media coverage. So there is. There is a desire in certain quarters for this case to be solved, and yet we know it hasn't been. So what is the immediate aftermath? What is the conversation that's happening after the St. Valentine's Day massacre in terms of how are we going to solve this? Who are we in pursuit of what is that and how does it percolate throughout Chicago and then throughout the states?

[Jonathan Eig]

Well, in Chicago, there's a lot of chaos, really, and no good leads. You'd think that Chicago police, you'd think that Chicago media, somebody would have tracked down some good clues. They do find one of the getaway cars burned in a garage. So there are some clues, but the police end up going nowhere in their investigation. One theory leads to another. Every day the newspaper has another idea about what might have happened and who might have organized this and who might have carried it out. But nothing sticks. At the same time, we're starting to see the national media and federal leaders, government in Washington, D.C. becoming frustrated that this looks bad. We've got a new president in the United States, Herbert Hoover, who has come into office. Remember, this is pre depression, so the economy's roaring, the nation's at peace, everything is great. And he's promising that he's going to clean up this lawlessness in our cities. It's really the first time that an American presidential candidate has used crime as a campaign issue, and it's very successful. He's saying that I'm going to bring calm to our cities. I'm going to do something about Prohibition. It's the law. And unless you want to change that law, we're going to enforce it and we're going to stop this chaos. And of course, some of that is anti immigrant, but it's also just, it's a very appealing message as it is today. So Herbert Hoover says, what are we doing about this situation in Chicago? Why haven't the cops done something? Why are there no arrests? And he makes it his mission to get Capone. He realizes even if Capone had nothing to do with it, this is the guy people associate with violence in American cities. He's the number one symbol of the problems of the gangland wars and that it would be just good publicity to take him out. It would send the message that we're going to get tough on crime. So Hoover becomes obsessed. And every Cabinet meeting, every morning, he asks for an update. What are we doing about Capone? Now remember, we don't know if Capone had anything to do with the Valentine's Day massacre, but because he's the biggest name in Chicago and the crime goes on, the longer the crime goes unsolved, Capone is like the sun. He's these, this, you know, everything is attracted to Capone. So the longer the crime goes unsolved, the more people assume, well, oh, it just must have been Capone. And maybe he did have something to do with it. But anyway, it doesn't matter after a certain point, because getting Capone is the answer to showing that we're tough on crime, showing that we're doing something about the Valentine's Day Massacre and about gangland Chicago, gangland America in general, I think.

[Maddie]

I mean, you could say that the massacre happens at a really opportune time for Hoover and comes as a sort of useful turning point or a way to signal that change is coming. And certainly it sounds from what you're saying, Jonathan, that his campaign sort of hinges largely on this idea of ungovernable violence. The repeal of Prohibition does come soon after this, doesn't it? Do you see that as a direct result of the massacre and its aftermath?

[Jonathan Eig]

Well, it's part of it for sure, because what happens after the massacre is that we do see the government coming after Capone. We do see them sending a message that they're not going to tolerate this kind of violence anymore. And at the same time, the Great Depression hits, and Herbert Hoover now has bigger problems on his hands. So one way to sort of end this wave after wave of terrible publicity, right? Hoover's being blamed for people losing their homes and losing their jobs. People who have no money becomes a symbol. They pull out their pockets to show they have no money, and they call those, those Hoover flags. The towns that people are living, homeless people living in tents, are called Hoovervilles. So. So he's got a huge public relations problem. And going after Capone is one way to distract the American public and then starting to talk about ending Prohibition, giving people their booze back, at least while they're going through these hard times, also becomes more politically acceptable. So Capone is caught up in all of this, and the Valentine's Day massacre is one important piece of that puzzle.

[Maddie]

The other thing that strikes me about this, the massacre and the sort of fallout of it. We've talked about the relationship between the gang and Prohibition and the relationship with the police, but I just want to talk specifically about the guns that are used in this crime as well. If, for example, we take it at face value that the police were involved, the guns that they use are those guns that the police would have had access to at the time, or are these guns that are used routinely by gangs instead? Is there any legacy from this massacre in terms of gun control after this moment has occurred?

[Jonathan Eig]

Well, to an extent, the problem that we see in the 1920s is similar to the problem we have now, where there are just so many guns on the street. Of course, now we have far more guns on the streets of America than we did back then. But this is sort of the beginning of the problem. It's very hard for the police to keep track of all the guns. These machine guns, these high artillery weapons that were invented for World War I, are now finding their way onto the streets and they're available in sporting goods catalogs. You can buy them anywhere. So. So it's very hard to know how many guns are out there. But also it's clear that it's being that it's escalating the violence and it's making it easier for people to kill one another, often, you know, from passing cars because the guns are so much more. So much more powerful.

[Experian Advertiser]

Yep, I inherited my dad's nose and his sign up for too many Subscriptions Gene. But I'm changing the family legacy with Experian. My BFF big financial friend Experian could help you cancel over 200 unwanted subscriptions and negotiate lower bills, saving hundreds a year. Now I can proudly say I also inherited great taste in apps. Get started with the Experian app now your big Financial friends helping you keep what's worth keeping. Results will vary. Not all bills or subscriptions eligible. Savings not guaranteed $631 a year average savings with one negotiations and one plus cancellations paid. Membership with connected payment account required. See experian.com for details.

[Jonathan Eig]

Experian.

[Professor Susannah Lipscomb]

I'm Professor Susannah Lipscomb and on Not Just the Tudors From History Hit we do admittedly cover quite a lot of Tudors, from the rise of Henry VII to the death of Henry viii, from Anne Boleyn to her daughter Elizabeth I. But we also do lots that's not Tudors. Murderers, mistresses, pirates and witches clues in the title really. So follow Not Just the Tudors from History Hit wherever you get your podcast.

[Anthony]

One of the things that happens in the aftermath of this, Jonathan, even if it's not directly related, although in some ways it is, is the downfall of Al Capone. Now it's not for this particular crime. Can you walk us through how Capone was eventually got to reference your book in a very messy way. But how did they manufacture this? In the end, I guess they didn't have to manufacture. There was plenty they could have gotten him on. But what route did they take?

[Jonathan Eig]

Well, as I mentioned, Capone was the subject of all these cabinet meetings and Hoover kept asking his every cabinet head, what are you doing about taking out Al Capone? And when it became clear that they couldn't pin the Valentine's Day Massacre on him, that they couldn't really pin any murder on him, that they couldn't even find evidence that he was bootlegging, that he was selling illegal booze because he wasn't doing it himself. It was a very decentralized operation that he led. And there were no receipts, very few records to show. So they couldn't find his business records showing how much booze he was selling illegally. He did it all on the sly. So finally, the head of the Treasury Department said, well, we could to make an income tax case against him. And only recently had the U.S. supreme Court ruled that illegal income was taxable. And that's a very important decision. Think about it. If you're making money illegally selling booze, selling drugs, running a casino, running a brothel, are you going to report that to your accountants and to the irs? I wouldn't. And of course, no one had. So the gangsters are now faced with this decision because their lawyers and their accountants are saying to them, you know, the IRS wants to know how much money you made last year. Actually, it was called the Internal Revenue Bureau at the time. It's now called the Internal Revenue Service. So Capone has actually called in for a meeting with the Internal Revenue Bureau agents and with his lawyer, and he's asked, hey, we noticed that you haven't filed taxes in the last five years. That could be a problem. We'd like to know how much money you made. And Capone's lawyer says, well, we'd be happy to make a settlement and pay whatever back taxes we owe. And maybe we could come up with. We could make a deal. Well, if there are penalties involved, we'll pay the penalties. You know, Capone wants to. Wants to get this out of the way, so he offers an estimate of how much he made over the last five years or so. And the IRS says, thank you for this. We'll get back to you. And they don't accept his offer to pay his taxes, but they begin now seeing if they could make a case against him for failure to pay taxes. So in a way, some of the people in the White House are nervous, like, like, is this wimpy? Like, are we going to look like fools? Al Capone's out there bragging about the fact that he's a bootlegger, that he's selling booze. He's obviously a stone cold killer. Are we going to be mocked for saying the only case we can make against him is he didn't pay his taxes? But ultimately, they make the practical decision the pragmatic decision that, like, it's better just to put them behind bars any way we can than to let him keep doing what he's doing and making a mockery of the law. And that's what they do. They build an income tax case against him.

[Anthony]

I'd be really curious to know, despite the fact that everything you've said there, you know, that there's a stone cold killer, that he has bootlegging going on, that he has all of this proper criminal activity going on. And at the same time, as we've hinted at before, this celebritization of the gangsters and the position that they possess on that level, was reaction to his arrest or his downfall? Was it a celebratory, yes, we got, we got him, he's off the streets. Or was it a bit of a. Oh, of course the, of course the authorities are going to try. We're all just trying to survive here. Like, what, what was the, the reaction?

[Jonathan Eig]

I think feelings were mixed. I think, you know, there's always a fascination with criminals, people who can get away with it. You know, we all dream of getting away with something, I suppose. And, and Capone was sort of a, you know, a mythological figure. People, you know, had this little love, hate relationship with him, just as they did with, you know, the Jesse James gang or, you know, there's a, there's a romantic element to this. And Capone, especially during prohibition, was giving the people what they wanted, which is one reason why he was constantly doing media interviews. He would say, I'm just giving people what they want. I'm doing the same thing. When they, when they serve drinks on Park Avenue, they call it hospitality. And with me, they call it a crime. Come on. And people, people related to that. In fact, when they did bring Capone to trial, they were really worried that the jury would favor him because jurors in Chicago were mostly drinking men and they were not inclined to convict bootleggers. There was. The government had always had a very hard time getting convictions of bootleggers. And now you're not even charging him with bootlegging, you're just charging him with failing to pay his taxes. And, hey, we all hate the irs. None of us really want to pay our taxes. So they were very worried that they were going to have a hard time finding jurors who were willing to convict. So Capone was still a hero to a lot of people, and the government was up against that. And we can talk about the trial if you want, because Capone really did get railroaded at his trial, he was obviously guilty. He hadn't paid his taxes. But to get that conviction, they had to throw out the original jury, bring in sort of a hand picked group of jurors that the judge thought he could count on to come up with a conviction. It was highly irregular. And Capone in many ways got a raw deal. I mean, like I said, he was guilty, but he got a raw deal in many ways.

[Maddie]

That's so fascinating that you speak about that kind of romantic element and, you know, compared him to Jesse James and that sort of the outlaw who is taking from the rich to feed the poor, as it were. I think that's very interesting and that he is sort of slightly mistreated by the authorities in that he gets this raw deal. What happens to him in the end? Obviously, he does go to prison. Jonathan, what do we know about, about the rest of his life?

[Jonathan Eig]

Well, he's only about 30 years old when he goes to jail, and he is sentenced to 13 years in federal prison for income tax evasion, which is unheard of. There had never been a conviction even half that length for income tax evasion. You know, income tax evasion is, you know, usually you pay your fine and maybe you do a couple years, but this was clearly meant to send a signal. And in fact, Capone has sent not just to federal prison, but after a little while in Atlanta's federal prison, he's sent to Alcatraz, which is built to house the toughest, baddest criminals, you know, on an island with sharks swimming around. Right. Like, why would they send a tax evader to Alcatraz? Well, once again, it's publicity. It's meant to send a message and to justify the government's cost of building this prison on an island in the middle of the San Francisco Bay. So Capone is very much a victim of, of the government's PR problem. And while in prison, he's diagnosed with syphilis, which is affecting his brain at this point. It's been untreated for a long time and he's beginning to really show signs of serious cognitive abilities. And by the time he gets out of prison, he's, you know, in his late 30s and he's pretty much mentally shot. So even though he lives another 10 years after prison, we don't hear much from Capone. He just spends his time, he's left alone. He still has one house in Miami that the government didn't seize, I guess because it was in his wife's name. And he just spends the rest of his days Sitting by the pool and fishing. We don't really hear much from him again.

[Maddie]

Yeah. It's such a banal end, isn't it, for a larger than life character? At the time we're recording this, the deadline in the UK for paying your tax is fast approaching. I'm starting to slightly sweat at the thought that I haven't gotten.

[Jonathan Eig]

Yeah. Let this be a good reminder.

[Maddie]

Yeah. Or I'll be off to Alcatraz. Jonathan, it's been so wonderful to talk to you and people who, you know, maybe haven't come across your work. Obviously, there's the Al Capone book and the recent biography of Martin Luther King for which she won a Pulitzer. What are you working on next? Can you tell us what a part of American history, if it is American history, has drawn your attention?

[Jonathan Eig]

Yeah, it's American history, but it's also world history. I'm writing a biography of George Soros, who may be as controversial as Al Capone in many ways.

[Maddie]

That sounds very exciting. When can we expect that to be out? Is that in progress now?

[Jonathan Eig]

It's in progress. It's a couple of years away, probably.

[Maddie]

Okay. I know that feeling well. In the meantime, where can people find you? Are you online? Where can they get more of your work?

[Jonathan Eig]

Yeah, my books and everything about me are available on my website, Jonathan I.com and you can get signed copies there and everything. So thank you for pointing that out.

[Maddie]

Fantastic. Well, thank you very much for joining us today and thank you, listener, for coming along to Prohibition Chicago with us. It's been a really fascinating and enlightening conversation. If you want to hear more gang histories, if you want to hear more about Prohibition, then you. You can get in touch with us with your ideas for future [e-mail] that's after darkstoryhit.com.

[LifeLock Advertiser]

It's tax season. And at LifeLock, we know you're tired of numbers, but here's a big one you need to hear. Billions. That's the amount of money in refunds the IRS has flagged for possible identity fraud. Now here's another big number. 100 million. That's how many data points LifeLock monitors every second. If your identity is stolen, we'll fix it. Guaranteed. One last big number. Save up to 40% your first year. Visit lifelock. Com specialoffer for the threats you can't control. Terms apply.