St. Valentines Day Massacre: Closing In On Capone | 3

0:08From Wondery, I'm Lindsay Graham, and this is American History Tellers, our history, your story.

0:30On the morning of February 14, 1929, seven men were gunned down in a Chicago garage. To this day, the so-called St. Valentine's Day Massacre remains officially unsolved, although at the time, most involved in the investigation suspected Al Capone had ordered the killings. Although he was never charged with ordering the murders, by the end of the Roaring Twenties, Al Capone had become the exemplar of the Prohibition-era gangster, and the feds set out to get him any way they could. In the end, Al Capone went to prison on charges of tax evasion. My guest today will help us unpack the story of how the feds closed in on Capone and what became of him in the years after his imprisonment.

1:09Jonathan Eich is the author of Get Capone, the secret plot that captured America's most wanted gangster. Eich also won a Pulitzer Prize for his 2023 biography of Martin Luther King. Our conversation is next. A friendly reminder, although Wondery Plus is going away on May 21st, you can still listen to this show on Audible or wherever you get your podcasts. To continue enjoying Wondery Plus listening benefits like early, binge, and ad-free listening, sign up for an Audible membership today on audible.com or the Audible app. Hello, American History Teller listeners. I have an exciting announcement.

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2:33Jonathan Igg, welcome to American History Tellers. Thanks for having me. So I think we should start with the big question. Did Al Capone order the St. Valentine's Day massacre? And if he didn't, who do you think may have done it? I think it's one of the great mysteries. It's one of the greatest unsolved crimes in all of American history. And you really have to unpack it to try to understand who might have been responsible. But I think that there's a good chance that some of the guys around Capone were involved in it. But bottom line for me is that we still don't know. All right. Well, who might be the leading suspects?

3:06Well, there are a lot of them. The problem with Chicago gangland in general is that there are just almost endless rivalries and almost endless numbers of competing gangs. So some people thought the Purple Gang out of Detroit or Egan's Rats out of St. Louis might have done it. Then there were other gangs in Chicago that were circling around, gangs that, you know, you probably haven't heard of. I think some of the guys associated with Capone were probably involved. You know, guys like Jack McGurn and Killer Burke. First of all, when you have the nickname killer, when you have the nickname machine gun, Jack McGurn, you're going to be a suspect.

3:41And of course, one big theory is that the cops did it and there were no gangs involved at all. When you think about murder in general, what do we know? It's usually a crime with some anger involved. But why would somebody want to kill seven people in a garage, including some people who were not involved in gangland activities at all? You know, there's a letter I found in the FBI archives that showed that a state employee had tried to alert J. Edgar Hoover to what he thought had really happened. And in many ways, it's a simple, plausible solution. This letter said that it was really a crime of passion, that a young man had been killed in a bar fight, gang members had been involved in that bar fight, and that the young man's father, who was a police officer, then arranged for his revenge.

4:24And that involved some gangsters. It involved some well-known killers. It's a complicated theory. It has a problem in that the main figure identified as the leader of that attack was in jail at the time. So there's some speculation that perhaps he was able to buy a pass from jail, get out for a while, long enough to commit this crime. But it's messy. And there's still not any clarity about whether that or any other theory holds up. You say you found this letter in the FBI archives. So that prompts me to think, because this crime, people were horrified by the massacre, grabbed headlines like no other crime in its day.

4:59And it also had an effect on the FBI and the new Hoover administration. So what effect did the St. Valentine's Day massacre have at the federal level? What's really fascinating about the Valentine's Day Massacre is what happened as a result of it. The crime itself, because it's unsolved, really tells us nothing. But it does tell us how the government used this crime to forward its own agenda. You know, at this point in 1929, Al Capone was incredibly famous. But his activity and his power were on a decline, actually. He was beginning to find it more and more difficult to operate. He was spending more time in Miami and Los Angeles.

5:38But the FBI and other branches of the federal government were on his tail. They were looking to find a way to take him down, in part because the new president, Herbert Hoover, wanted to prove to Americans that he was going to be tough on crime. You know, with the Great Depression underway, Herbert Hoover was under all kinds of pressure. Obviously, the prohibition laws were wildly unpopular. Not only were people still drinking, but it had spurred this massive wave of crime with gangsters killing gangsters and going unpunished for it. So the Valentine's Day massacre horrified Americans. It was not just seven dead.

6:13It was seven dead with gruesome newspaper photos on the front page of tabloids. And I think that it really sparked something for the president, for Herbert Hoover, that this was something that needed to be addressed. He really became obsessed with Capone. Hooper would ask every member of his cabinet, what are we going to do to get Capone? And Herbert Hooper was very much a bureaucrat. He was very much about reforming the laws and appointing committees. But he also recognized the importance of public relations. And he thought the best way to send the signal that I'm going to get tough on crime is by making an example of Al Capone.

6:48He's the most famous criminal in America. So maybe if we can't pin the Valentine's Day massacre on him, we can at least use the anger, the public resentment about this crime, this ongoing crime, to build momentum, to build support for taking out Capone. Let's talk about Capone a little bit and his business empire. I mean, if you were a gangster in 1920 Chicago, you could make money in any sort of ways, bootlegging, gambling, prostitution, racketeering, you name it. But once Al Capone rose in the ranks of the West Side Gang, give us a sense of his business interests, what he called the outfit. The outfit is a very loose-knit structure.

7:24Remember, this is all brand new. You know, Capone's an immigrant's son, and he's making a living. Some of his work is criminal. Some of it isn't. And when Prohibition comes, suddenly there's this opportunity that he never dreamed of to make far more money than he ever imagined. And he's already comfortable breaking the law. Prohibition created this opportunity to go beyond the usual stuff, the brothels and the casinos. Suddenly, Prohibition gives these two-bit hoods a chance to get into a much bigger business, to take over one of the largest industries in America. the beer and wine and alcohol business.

7:57So they're flying by the seat of their pants. And every city has somebody like Capone. Every city has lots of Capones. The challenge is that they're not sophisticated businessmen, obviously. They're having to do all of this quickly, improvisationally, and they're making it up as they go along. So the business has become incredibly sprawling, incredibly loosely organized. And it really just depends on your tolerance for chaos to run one of these organizations. So do you believe that Capone had a tolerance for chaos? Yeah, Capone had huge tolerance for chaos. He had to. I mean, think about it. He's ordering beer for his customers, for his bars, for his saloons, for his brothels.

8:37You know, where can you find this stuff? They're paying people to manufacture gin in their basements. And he doesn't own the brothels. He doesn't own the bars, the speakeasies, the casinos. He's just taking a cut of all these businesses. So how do you keep track of all that? He's got a good accountant, but still, it's so easy to skim money. It's so easy to fake the books. And he's got to be able to rule with an iron fist in that, you know, if someone screws you, you go after them. If somebody tries to cut him on your turf, you go after them. But even so, there's no way he can keep track of what's happening in this vast criminal enterprise of his.

9:13I think Capone thought of himself, first of all, as a businessman. He felt like he had moved beyond being a thug to being this businessman because he was operating this incredibly large, loose-knit organization and somehow making it all work. And, you know, obviously violence was required sometimes to rein in or to erase problems. That's why he dressed the way he did. He wanted to be seen as a serious businessman in this new wild era where money was being made in incredible sums. Think about what was happening with the stock market, right? That too is out of control, but seems like it's just going to keep going and going and going.

9:47And he felt the same way, that this business is crazy and chaotic, but the money is coming in so fast and so easy that I just got to keep riding that wave. It occurs to me that this chaos may be part of his shield. Capone seemed untouchable early on. Chicago law enforcement, you know, they haul him into court, but nothing really sticks. Is it because he has his finger and finger only in so many pies that he seems to be incapable of being arrested or convicted? I think that's right. I I think because Capone isn't keeping paperwork, because he knows that this is an all-cash business, and he's smart enough to recognize that putting his name on a bank account or putting his name on an invoice is going to be a huge mistake because it leaves a paper trail, the chaotic nature of his business actually becomes a strength because it's almost impossible to prove that he's involved in anything.

10:38And that becomes the big challenge when they seek to make a case against him. You know, you can break down the door of a brewery and chop up the barrels with axes, but you're not going to find paperwork in there that says Al Capone's take on this month's sales is X amount. You're not going to find checks. You're not going to find invoices that have Capone's name on them anywhere. But he's not completely untouchable, right? The authorities came close after the Pony Inn shooting. Yeah, the Pony Inn shooting is the closest Capone comes to really getting in serious trouble. That was 1926. Up until that point, Capone has been operating almost completely free of risk.

11:16He owns the police department. He owns the courts. He's paying off people in every corner of government so that he's protected. He even laughs about it one time when he gets pulled over for drunk driving. He says, you know, I'll be out before you can finish your paperwork. And he is. He's released almost immediately. But the Pony Inn shooting becomes a different story because one of the victims is actually an assistant state's attorney, a prosecutor. So, you know, if gangsters are shooting each other, nobody gets too upset about it and nobody gets charged. In all of the cases of gangland shootings, there are virtually no convictions in Chicago.

11:51But the Pony in shooting, you've got Billy McSwiggin dead. He's a state prosecutor. And suddenly there's serious pressure to investigate this crime, to solve it. And Capone recognizes that this is a kind of heat that he hasn't faced before. So he takes off. He leaves town. And he's got a big decision to make. This is really, in some ways, the make or break moment for Capone. Because at that point, he could have said, you know what? I'm going to take my money and go. I'm going to walk away from the table. I've made enough. It's not worth the risk at this point. But he makes a crucial decision, not just to come back and to resume business, but to sort of embrace the celebrity involved with his role.

12:28To say, yeah, I'm a gangster. Yes, I'm a bootlegger. So what? You know what I'm doing. People want my product. And the politicians and the cops, they all know what I'm doing. So what do you want to know about McSwiggin? He was working for me. He was on my payroll. Why would I kill a guy that I was invested in? So it's fascinating because he's basically going public. You know, it's almost as if, you know, he'd met with his team of publicists and said, how are we going to handle this? Let's go high on this. Let's just pretend that we know what we're doing and we're in control here. and there's nothing criminal.

13:00Why would I kill a guy that I was already bribing? I'm glad you mentioned Capone's celebrity. Certainly, it's part of his myth. But this was also the Great Gatsby era, right? The Roaring Twenties, a time when millionaires threw lavish parties and champagne float in the streets. But how flashy was Capone really with his money compared to some of the other high rollers of his time? Well, compared to the other high rollers, he wasn't all that flashy. But compared to gangsters, compared to bootleggers, he was very flashy. Capone dealt almost entirely in cash. And I think some of his associates used to lock up the vaults because they were worried Capone would just keep taking more and more cash.

13:36And he gave it away. He spent it lavishly. He gave huge tips. He loved to dress in a really flashy manner. He would go for these pinstripe suits, but he wanted to look more like a banker than a banker. So he would get wider pinstripes and bolder colors and sometimes really bold, like bright green pinstripe suits. And he actually sought media attention. He gave interviews. He invited reporters from women's magazines to his office to talk about what it's like to be a family man and a gangster. You know, it's it's crazy. And he brags. He says, you know, I'm just giving the people what they want. It's hospitality when they do it on Park Avenue.

14:12But they call me a criminal for doing the same thing. So he's really trying to change the narrative. And frankly, you know, a lot of other gangsters, a lot of other bootleggers are horrified by this. Why are you calling attention to yourself? You're just asking for trouble. And it turns out that he was asking for trouble by making himself the most prominent underworld figure in America, by making himself internationally known. He put a target on his back. Let's talk about the narrative and how Capone crafted it, because he also developed something of a Robin Hood notoriety. The public had some sympathy for him and other bootleggers.

14:47People didn't love prohibition, and they loved to drink instead. Capone tapped into that, and he liked to talk to the press, as you mentioned. So how did he work his image in the newspapers? Capone really was smart about this. He recognized that people wanted a drink, and he was the one providing the drinks. The government was the bad guy. Why would you take away our booze? America's a country of freedom. We don't take away rights. We're adults here. He's also incredibly generous, spreading the money around. He's providing jobs, you know, truck drivers and barrel makers, as well as distillers.

15:18And he's spreading bribes around as well. Capone's a celebrity. when people come in from out of town. Back then, you'd come in for a big weekend, your honeymoon. You might go from Iowa, drive into Chicago. There'd be magazines you could buy filled with pictures of Capone. Some of them would have crime scenes too. The crime was a part of the allure. And later, when the Great Depression hits and he realizes that Herbert Hoover is on his back and Herbert Hoover is being blamed for people starving and losing their homes, then Capone takes it up a notch and opens a soup kitchen and says, look, the government doesn't care about you.

15:50It's very savvy, public relations. This public relations savvy, do you think it's a strategy or is it just his own charisma? Oh, I think it's both. I think it's very much his personality. He's very charming and outgoing. He's gregarious. He likes people, likes to go to sporting events. And I think he genuinely wants to be a regular guy. And he enjoys the fact that he's got this money. But he's also really trying to earn sympathy. He's given these interviews where he's saying, you know, I'm a dad. I want my boy to grow up with a father. I want my wife to, like, her hair's turning gray. At one point, he actually asks his wife to come in the room to show this reporter that, look, her hair's turning gray.

16:30Look how worried she is. So it's fascinating to see this cold-blooded, ruthless criminal also begging for sympathy and wanting to be understood. And I guess it's just a reminder that even the bad guys are human in a way.

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18:53Earlier, you mentioned that Capone's profile put a target on his back. And in 1927, at least two things happened that year that would really have a big impact on Al Capone and perhaps broaden that target. Let us know what they are. Well, for one thing, the Supreme Court decides that illegal income is taxable. So think about that for a second. If you have illegal income, whether you're stealing from your bank, from your own employer, or if you're robbing people at gunpoint, are you going to declare that on your taxes? Are you going to describe that you made this money by stealing paintings and fencing them, right?

19:31No, you're not going to do that. But it presents a new question for Capone. What's he going to do if the IRS comes knocking? And then they do come knocking. First, they come after his brother. His brother is persuaded to fill out a tax return, claiming some income. And the Internal Revenue Bureau, as it was called at the time, uses that to build a case against Ralph Capone. And then Al is next in their sights. What's the second thing? So as Capone is rising to power and gaining fame and the federal government is having a hard time putting him away, remember, crime at this point is enforced almost entirely by local law enforcement officers.

20:08The federal government doesn't go after local criminals. That's the police department's job. But the police department won't go after Capone. So now the feds are thinking, how do we do this? The FBI is still, you know, a new organization that's not famous for going after local criminals. That's coming later. So as the feds begin to think about how to go after Capone, they turn to the U.S. attorney for Chicago. His name is George E.Q. Johnson, in part because he's unbribable. He's one of the few honest men in the judicial system in Chicago that the feds think they can count on. So the U.S. Justice Department says to George Johnson, get Capone, go after him, whatever it takes.

20:45We don't care what kind of case you make. Obviously, it'd be great to get him on a murder charge or on a bootlegging charge. It's going to have to be some kind of a federal crime. What can you do? And Johnson struggles with this. He really can't find any proof that Capone is bootlegging, can't tie him to the Valentine's Day massacre or any other crime, and finally settles on income tax evasion. And it's controversial. They're worried that it'll look weak. Here's this guy who's bragging about all his crimes, and the only thing you can get him for is not paying his taxes. But George E.Q. Johnson makes the decision that it's more important to get him off the streets, to get him behind bars, than it is to worry about how you do that.

21:22Now, in the writing of your book, you found boxes of U.S. Attorney George Johnson's notes and papers at the University of Nebraska at Omaha. What did they tell you about this man and his game plan to get Capone? George E. Q. Johnson's boxes, which had not yet been archived, his papers were still just sitting in cardboard boxes in a professor's office in Nebraska. They're fascinating because they reveal how difficult it was to make a case and how the government had to really bend over backwards and sometimes even cut corners. I think, you know, today, if Capone had the right lawyer, the entire case would have been thrown out because the feds made so many questionable calls in trying to put him away.

21:59And the trial itself was really flawed in many ways. Capone gets railroaded, but George E. Q. Johnson is determined that he's going to get Capone, and he determines that the only way to do that, finally, is income tax evasion. That's the only charge that he thinks they can make stick. But it is true that after the St. Valentine's Day massacre, Al Capone spent nearly a year in prison on weapons possession charges, getting out in March of 1930. And in June 1930, Al Capone's brother, Ralph, was sentenced to three years in federal penitentiary for income tax fraud. Capone, perhaps realizing that he'd better deal with his tax bill, in September of 1930, he has his lawyer submit a letter to an internal revenue agent.

22:40What did this letter say? The letter from Capone's lawyer admits some income. So Capone lists his income for the past several years, something like a quarter of a million dollars. And I think the letter's intent is that they're going to try to come to an agreement, that they're going to have a fine, that they'll pay some back taxes and Capone will be off the hook. I think that's what Capone and his lawyers are shooting for here. And he does this because he doesn't want to end up in prison like his brother. But the IRS, or the Internal Revenue Bureau, it was called at the time, says, thanks for the information, we'll get back to you.

23:12And they don't want to make a deal. In fact, they're going to use this admission to build a case against him. How did Capone miscalculate so badly? Well, first of all, some of it's the fault of his lawyers. His lawyers should have said that, in advance that this agreement can't be used as evidence against us, right? If we were going to submit some estimates of our income, this should not be used against us later if you're going to try to charge us with income tax evasion. So that's a big mistake. And maybe Capone's lawyers could have gotten that thrown out as evidence, saying that this was part of an attempt to reach a settlement and not an admission of actual income.