Chapter 1: What is the main topic discussed in this episode?
From Wondery, I'm Lindsey Graham, and this is American History Tellers, our history, your story.
Chapter 2: What happened during the St. Valentine's Day Massacre?
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 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. Jonathan Ige is the author of Get Capone, the secret plot that captured America's most wanted gangster. Ige also won a Pulitzer Prize for his 2023 biography of Martin Luther King. Our conversation is next.
Chapter 3: Did Al Capone order the St. Valentine's Day Massacre?
Jonathan Eig, 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.
Chapter 4: Who were the main suspects involved in the massacre?
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.
Chapter 5: How did the St. Valentine's Day Massacre impact law enforcement?
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. 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 someone? 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.
Chapter 6: What was Al Capone's business empire like during Prohibition?
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 horrified by the massacre, grabbed headlines like no other crime in its day.
Chapter 7: How did the federal government eventually target Capone?
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.
Chapter 8: What evidence led to Al Capone's conviction for tax evasion?
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. 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 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 1920s 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.
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 industries 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 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 businesses become incredibly sprawling, incredibly loosely organized, and it really just depends on your tolerance for chaos to run one of these organizations.
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