American History Tellers - St. Valentines Day Massacre: Closing In On Capone | 3

Episode Date: February 18, 2026

In the aftermath of the St. Valentine’s Day Massacre, authorities faced mounting pressure to clean up Chicago and take down the violent mobsters who overran the city – most notoriously, Al Capone. The federal government took on the challenge, pursuing Capone relentlessly. In the end, Capone did go down – not for murder, but for tax evasion. And since Capone’s conviction in the 1930s, this unorthodox charge has been used repeatedly to bring down otherwise “ungettable” criminals. To discuss how the feds finally closed in on Capone, Lindsay speaks with Jonathan Eig, the Pulitzer Prize–winning author of Get Capone: The Secret Plot That Captured America’s Most Wanted Gangster.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

From Wondery, I'm Lindsay Graham, and this is American History Tellers, Our History, Your Story. On 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 20s, 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. Jonathan Haig is the author of Get Capone, the secret plot that captured America's most wanted gangster. Haig also won a Pulitzer Prize for his 2023 biography of Martin Luther King. Our conversation is next. Jonathan Ige, 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? Well, 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 McGern and Killer Burke, first of all, when you have the nickname Killer, when you have the nickname Machine Gun, Jack McGern, you're going to be a suspect. And, 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? all. You know, there's a letter I found in the FBI archives that showed that a state employee had tried to alert Jay 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. And 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, were horrified by the massacre, grabbed headlines like no other crime in its day, and 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. But 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 of 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. It 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. Hoover would ask every member of his cabinet, what are we going to do to get Capone? And Herbert Hoover 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. He's the most famous criminal in America. So maybe if we can't pin the Valentine's Day massacre on him, we can't 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 interest, what he called the outfit. The outfit is a very loose-knit structure. Remember, 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 industry. in America, the beer and wine and alcohol business. So they're flying by the seat of their pants. And every city has somebody like Capone. Every city has lots of Capone. 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 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. You 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. I 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. And 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 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. 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. And that becomes the big challenge when they seek to make a case against him. 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 in shooting. Yeah, the pony in 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. He 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 in 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 kind of convictions in Chicago. But 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, to say, yeah, I'm a gangster. Yes, I'm a bootleggar. 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. Why 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 20 is a time when millionaires through 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, and 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, you know, wider pinstripes and bolder colors and sometimes really bold, like bright green pinstriped 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 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, but they call me a criminal for doing the same thing. So he's really trying to change the narrative. 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. Well, 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. People 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, and 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. It'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 at the room to show this reporter that, look, her hair's turning gray. Look, 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. Hello, American History Tellers, listeners.

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Come see my days that made America tour live on stage. Go to American History Live.com. Earlier, 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? No, 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 that 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. enforcement officers. The 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 EQ Johnson, in part because he's unbrivable. He's one of the few honest men in the judicial system in Chicago that the think they can count on. So the U.S. Justice Department says to George Johnson, get Capone, go after him. Whatever it takes, we don't care what kind of case you make. Obviously, it would 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. Now, 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.C. 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. And the trial itself was really flawed in many ways. Capone gets railroaded. But George H.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. What 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 is called at the time says, thanks for the information, we'll get back to you. And 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, you know, in advance that this agreement can't be used as evidence against us, right? If we're 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. But one of the problems Capone had is that he didn't hire the right lawyers in many instances. He hired people who had been so successful for him over the years in dealing with criminal cases, criminal charges, but not experts in tax law. So he makes some admission of income. Surely he's not actually telling the truth. No, he obviously vastly underestimated his income, but that's sort of human nature, right? Like, he didn't have any idea how much money he was making. He wasn't keeping books on this. So he's just trying to figure out how to get out of this mess. So the news is being drawn around Al Capone's neck. And if we take the movie The Untouchables as Gospel, we would think that Elliot Ness is the guy who hunted Al Capone down. But from your research, it seems that we should be talking about Frank Wilson, who would. was he? Frank Wilson was one of the internal revenue agents, and it was really the Revenue Bureau that did the heroic work here. They were the ones digging up books, looking for accounting

ledgers, looking for proof of Capone's empire, proof of his income. And it was very hard to do. As I said earlier, he didn't keep books. So they were very fortunate, and they found one ledger that indicated payments to Al. It was handwritten, and it didn't say Al Capone, just said Al. So they had some evidence that he was receiving income from brothels and casinos and from speakeasies. But even then, the case that they ended up bringing relied mostly on proof of his spending. It was a very circumstantial evidence. But the IRS agents were cobbling together everything they could. And Elliott Ness was of no help. The indictments that he brought for bootlegging never really factored into the attempt to put Capone away. So then how did Elliot Ness become the name

we remember. Well, Elliot Ness, like Al Capone, turned out to be really good at marketing himself. Late in life, after Elliot Ness served as a police commissioner in Cleveland, he went to work on a memoir with a terrific ghostwriter. And the ghost writer actually ended up completing the book after Ness had passed away and just spun this fabulous fable. Much of it fictionalized about Elliot Ness's confrontations with Capone and his breaking down doors and busting speakeas and and brothels and breweries, but much of it was fictionalized, much of it was exaggerated. You mentioned Revenue Investigator Frank Wilson as the perhaps true hero in the capture of Capone and the break he got in finding this one ledger. I'd love you to give us a little more detail

about the story behind this led to Capone's arrest and conviction. Well, one of the great things about accountants is that they love the books and they'll dig through books and paperwork and receipts until their eyes go bleary. And Frank Wilson, along with some of the other people on his team, were just relentless. And there was a bust of a brothel or a casino in the suburb of Chicago. And during that bust, a bunch of books were seized. And late one night going through file cabinets, just looking for something he might have missed. Frank Wilson came across this ledger from the casino that had been busted earlier.

And in that ledger, he found mention of payments being made to Al. And that was it. That was really the only hard evidence they had showing money flowing to Al Capone. But Frank Wilson wasn't just an accountant. He actually, in this case, got to do a little bit more traditional police work because they needed to know whether this Al mentioned in the ledger was actually Al Capone. So Wilson arrested the bookkeeper at the ship, this bar that had been busted where they found the ledger. And the guy wouldn't talk. You know, as everybody knows in the underworld, you know, you don't talk or you're going to face problems with the big guy. Wilson put this guy in a cell far away from home and just sweated him out until finally the guy agreed to start talking and to cooperate as a witness.

And they made a deal where they would protect his identity. And finally, that was some of the key evidence that led to the indictment of Capone. Something that we don't really know about this indictment of Capone is that it was a bit of a race against the clock because there was a statute of limitations for filing charges. How close did they cut it? It was a close call. and George Johnson was under a lot of pressure. He was under heat from Washington. He had two days before these statute of limitations would expire on those tax evasion charges.

So he was able to get an indictment on one count for just one year of unpaid taxes. And he was able to squeeze that in two days before the deadline. But even then, you know, people in the Justice Department were debating whether this was the best they could do. Is this going to make us look weak? You know, are we going to be mocked for filing this petty charge, this tic-y-tack technical case against Capone, this gangster who brags about his criminality, the best we can do is one count of income tax evasion, but the decision was made to go ahead and do it

because they had no other choice. So U.S. attorney George Johnson announces the indictment of Al Capone on charges of income tax evasion. And it seems that Capone and his lawyer still think that this is mainly a money issue because they cut a deal in return for a guilty plea. How'd that go for them?

This is another one of the instances in which the case against Capone really seems to be shoddy. Capone's lawyers go to the federal government. They go to George Johnson and they say, let's make a deal. You know, your case is weak. You might lose and how embarrassing is that going to be will agree to a deal. Copone will do a couple of years. He'll pay a fine. You can say that you prosecuted them successfully. And the federal government agreed to that because George Johnson really was worried that he could lose this case at trial to find a group of jurors that are willing to convict a bootleggers hard in Chicago. Most people have some sympathy for the bootleggers. So Johnson agrees to the this plea deal, Capone agrees to the plea deal, and then at the last minute, the judge squashes it, says, no, we're going to trial. Well, tell me about this judge and how he was able to undercut the deal that was made. Well, Judge Wilkerson was a wildcard here, and he was getting pressure from Washington to make sure Capone did some serious time. And when the plea bargain came in,

it had to be approved by the judge. And Capone had agreed to two and a half years. George Q. was content with that. He wanted a sure thing. He wanted to get Capone off the streets. And when they came before Judge Wilkerson, Wilkerson said, no, I'm not happy with this. You don't get to make this plea bargain without my approval, and I don't approve. So we're going to trial. And Capone's lawyers and Capone himself were flustered. You know, they thought they had made a deal. They thought that this was set. On what basis did the judge make his decision? No one knows why Judge Wilkerson threw out the plea bargain, but we do have a couple of clues. One is that Capone made the really stupid mistake of bragging about his plea deal to reporters before it was announced. And that may have really

infuriated the judge. It may also have infuriated the president because we do know that one of the emissaries of President Hoover visited Judge Wilkerson just a couple of days before the plea bargain was to have been approved. But in all likelihood, Wilkerson was just concerned or upset that it's going to look like Capone was getting off easy. And before the trial began, Judge Wilkerson threw out the jury and insisted on a new jury and used a handpicked jury of people who had served on other juries that had convicted bootleggers, including several jurors who had been on the case that convicted Ralph Capone of income tax evasion. Frank Wilson got word that Capone was trying to bribe the jurors. And that is one reason why Wilkerson may have swapped out the jury at the last minute and brought on this group

that he could depend on. They were all rural Chicagoans from the outskirts of Cook County, which prompted Damon Runyon, who was covering the trial, to say that every time the jurors came into the courtroom, it smelled like turnips and hayseed. So this was a sign that the deck was stacked against Capone. But that wasn't the only stumbling block for Capone. He had his own lawyers to deal with.

Yeah, his lawyers were not experts in tax law, and they were making mistake after mistake. They were failing to object to things that they might have been able to use to file appeals later. So they made one mistake after another. Capone was really done in by his own lawyers as much as by the prosecution. The government alleged that Capone made, you know, hundreds of thousands of dollars based on, in part, the fact that he had tried to make a deal to pay his taxes. And his lawyer had said he'd made something like, you know, a quarter of a million dollars over the course of several years. He probably made a lot more, but they couldn't prove it. All they had was this admission made in the course of an attempted settlement, which is questionable. And it probably should have been. protected. It probably should have been excluded as evidence because it was an attempt at negotiating a settlement. Now, in this trial, Capone wasn't the only one struggling, he and his lawyers. The federal government did not have a great case either. So how did they make this stick? The problem was, as we said

earlier, they have nothing but one ledger that mentions Al, doesn't even say Al Capone. There are no checkbooks with Capone's bank account. There's no accounting to show how much money was bringing in. So they're saying Capone is earning millions of dollars, huge amounts of money. how do they prove it to the jury? Well, they can't. So instead, they build a case by showing Capone's spending. They're showing how much he's spending monthly on stakes, how much the curtains at his house cost, how much he's spending on clothing at his tailor, and how much his house in Miami

cost. All of this is circumstantial evidence. They're saying to the jury, we don't know how he made his money, but we know he's got money. And if he's got money, he should have paid taxes on it, and he didn't. So it's requiring a leap of faith. and that's the leap of faith that the jury is willing to make. It became clear enough this guy had a lot of money.

Who knows how much, but he didn't pay a penny of taxes, so he was going down. So before the trial started, Capone had already reconciled himself to going to prison for two and a half years, but that was not the sentence he got. How long was he to be sent away, and how did he react? Capone agreed in this plea bargain to two and a half years, and that was thrown out. So he might have thought that he'd get three or four years. So when he was sentenced to 11 years, you could imagine he was stunned. I think a lot of people were stunned.

And I think, though, he kind of jokes about it with his lawyers after the sentence. He says, OK, well, I'll see you. Looks like I'm going to be gone for a while. He knows that he was playing dirty his whole career. He knows that he got away with all kinds of things, possibly including murder. And now, in a way, this isn't the way the justice system is supposed to work, but there's some karma involved. Like, he knows that he's been had. He knows that they got the better of him.

and he's going to have to do his time. Al Capone, of course, went to prison on November 24, 1931. He got out of prison in 1939 after serving time in the notorious federal penitentiary of Alcatraz. And he left that place, a much diminished man. What was the rest of his life like? It's fascinating. We forget, first of all, how young Capone was when he was at the height of his powers. He was in his early 30s.

And then he goes away to prison and is diagnosed almost immediately with tertiary syphilis. So he's discovered that he's got a neurological condition, and he's slowly and steadily declining mentally and physically. So by the time he leaves prison, he's really in poor shape. He's basically 40 years old, but he's racked with dementia from syphilis. In most cases, you know, if he'd been healthy at age 40, he could have had a whole new life. He could have, today he'd be hosting a podcast for sure. He'd be a celebrity, but he just disappears. He stays at his home in Palm Island, Florida.

It was in his wife's name in Miami. He fishes. He smoked cigars by the pool. At some point, some people said his mind was so far gone that he would just toss a tennis ball into the net over and over again, like a puppy chasing the tennis ball. He's incoherence at times. He's almost childlike in his behavior.

And sometimes people said that he had paranoid delusions that someone was coming for him. You'd see a headlight coming down the road and he would think that, you know, they were coming to assassinate him. But his mind was clearly failing him. And those last years were really just spent alone. And January 1947, he dies.

He's only 48 years old. But interestingly, the government never seized the house that his wife owned. And the question has often remained, like, what happened to Capone's money? If he really made these millions that the federal government claims, what happened to all the money that he made? Did he not make as much as we thought that he spent it all as fast as he was making it? Or some people have speculated over the years is there a big suitcase or many suitcases of cash, somewhere to this day. I suspect he never really accumulated any great wealth because he was just spending it and giving it away as fast as he was making it. He had one son and that son ended up

living a very quiet life, never got involved in anything criminal. He was arrested once for shoplifting and that became a big national story. Al Capone's son arrested for shoplifting. But other than that, he appears to have lived a spotless life and had some daughters of his own. So Capone had some grandchildren. But his legacy really was his story. If there is a a lesson for the federal government and how it got Capone? What is it? Well, actually, one of the great consequences of the Capone investigation is that the government did learn a lesson. And the lesson is that it worked, that they did the right thing, in essence. And it's a lesson that we now see applied in many instances when the federal government is looking to take out someone who they think is a

terrorist or might be a terrorist. The first thing they do is they check their visa. They look through their bank statements. They look for income tax violations. Because if you can't prove that somebody is guilty of the more serious crime, the important thing is to take them out, to get them off the streets, to eliminate the danger that they represent. And that is still to this day called a Capone-style case, because the real important lesson that we take from the investigation of Al Capone is not that a terrible criminal was punished in the manner in which he deserved to be punished. The real lesson is they found a technicality, they got them off the streets, and it's served in many people's view of the public good.

Jonathan Igg, thank you so much for talking with me today on American History Tellers. Thank you so much. That was my conversation with Jonathan Igg, author of Get Capone, the secret plot that captured America's most wanted gangster. Jonathan Igg also won a Pulitzer Prize for his biography of Martin Luther King Jr. in King Alife. In our next series, we're bringing back a fan favorite, great American authors, from the macabre imagination of Edgar Allan Poe to the quintessentially American adventures of Mark Twain, to James. James Baldwin, searing insights on race, we explore the remarkable lives behind the works that have shaped our nation's literary consciousness. From Wondery, this is the third and final episode of our series on the St. Valentine's Day

Massacre. American History Tellers is hosted, edited and executive produced by me, Lindsay Graham for Airship, audio editing and sound design by Molly Bach, music by Thrum. This episode is produced by Polly Stryker. Managing producer, Desi Blaylock. Senior producers are Elita Rizanski and Andy Beckerman. Executive producers Jenny Lauer Beckman and Marshall Louie for Wondering.