(tense thoughtful music) - I don't think anyone could have predicted that John Dillinger would become the arch-nemesis of the FBI, which he did.

- If you're the chief of police of St.

Paul, all you care about is low crime in St.

Paul.

That's your job, right?

- And I think he knew immortality was behind the lens.

(clock ticking) (tense dramatic music) - So in the 1920s, obviously, Prohibition was alive and well in America, which meant that there was an entire underworld of bootleggers and rum runners who were providing liquor to America.

And this was prevalent all over the country.

But in the Midwest in particular, you know, there were gangs of bootleggers and, you know, places like Chicago and Detroit and St.

Paul, that were very active and were regional.

They were increasingly focused on providing liquor, not just in their own city, but all over the area.

- Minnesota was extraordinarily well-positioned to be a crime haven.

Part of it is during Prohibition, it was a great place to make illegal liquor because we had the Mississippi River nearby, great water, we had a lot of Germans who knew how to make beer.

But then, when Prohibition was repealed, what did all those bootleggers do?

They turned to bank robbery.

They turned to kidnapping.

(clock ticking) (tense dramatic music) - The Great Depression was a devastating thing.

And it led to mass unemployment, led to people losing their farms, losing their businesses, going, and for the first time in their lives, they're standing in bread lines, trying to find food for their families.

There's a lot of desperation.

There's a lot of concern about "What are we gonna do tomorrow?"

- In the wake of the Depression, nobody liked the banks.

The banks, during the Depression, foreclosed on the houses and the farms.

- And so if you are a bank robber, you suddenly are the good guy, right?

And the bank is the bad guy.

It was an upside-down world for a while there.

So that a person, like a John Dillinger, who was going around robbing banks, is like a Robin Hood character.

- So when banks were robbed, people kind of shrugged and said, "Well, they got what they deserved, 'cause they foreclosed on my farm."

(tense thoughtful music) So the Dillinger Gang, along with almost every major bank robber, kidnapper, and mob hitman in America, was attracted to Minnesota, and specifically St.

Paul, but also in Minneapolis, because we had the deal.

It was safe haven.

Dillinger could walk down St.

Peter or Wabasha, or University Avenue in St.

Paul.

And he was famous.

He was as famous as Babe Ruth, as O.J.

Simpson is today, notorious but famous, and no one would turn him in.

There's Public Enemy No.

1 walking down St.

Peter in St.

Paul, and he was safe.

That was a big attraction.

- So, you know, at this period of time, the 1920s and '30s, one of the sort of focal points of crime in the Midwest was St.

Paul, Minnesota.

St.

Paul was a unique situation in that it was a place that was a magnet for criminals.

It was a place where they could go and feel like they had safe harbor from being caught, from being imprisoned.

And the reason they felt that way is 'cause they could.

(laughs) A system was set up called the Layover Agreement that said, if you come to St.

Paul, if you're a criminal, you're a bank robber or a thief, or whatever you are.

If you come to St.

Paul, and you come, and you tell people you're here.

In other words, you tell the right people in the underworld that "I'm here, I'm in St.

Paul, and here is my payment."

In other words, some kind of a bribe.

It's not a lot, but enough to sort of show that you want to take advantage of their hospitality, if you will, and that you agree that you're not going to commit any crimes within the city limits of St.

Paul, then nobody's gonna bother you.

- I thought, "Oh, the good people of St.

Paul, they couldn't have known that this deal was between the cops and the crooks."

How wrong I was.

As early as 1914, the official St.

Paul police yearbook described the O'Connor system publicly.

You could go into the library today and see it.

And it literally said, "As a result of our understanding with the criminal element, never in the history of Minnesota have the people of St.

Paul been so safe and the virtue of our women so secure."

I love that.

They're welcoming the criminals, but as long as the women... Yeah, okay, yeah, that's good.

So it wasn't even a hidden secret.

It was an open secret.

Everybody knew the fix was in.

- There was a lot of crime around St.

Paul within, you know, an hour or two.

The reality was, if you're the chief of police of St.

Paul, all you care about is low crime in St.

Paul.

That's your job, right?

- So the people of St.

Paul figured they'll rob a bank in Madison, Wisconsin, but they won't hurt us here.

And they accepted the dirty deal.

- Now, what that ultimately meant is you could drive, you know, a few miles to the west and go to Minneapolis and rob a bank, and "That's fine.

We don't care.

As long as you don't commit a crime in St.

Paul, you know, then we're fine.

You can do whatever you want."

- Another reason to come to Minnesota, in addition to easy access to submachine guns, gun molls who would love you, getaway cars.

And Minnesota was a great city to launder money.

You could kidnap someone, as the Barker-Karpis Gang did in another city, and then launder, clean the money through a guy named Harry Sawyer or Jack Peifer of the Hollyhocks Club in St.

Paul.

Basically, Minnesota was a Walmart for crooks.

(lively piano music) - [News Reporter] John Dillinger began his career of crime in Mooresville, a quiet Indiana town southwest of Indianapolis.

- John Dillinger, we know today, was one of the more prolific bank robbers of the 1930s.

When he grew up, he was a bit of a juvenile delinquent.

He would break windows; he would steal cars.

He loved baseball.

So I don't think anyone could have predicted that John Dillinger would become the arch-nemesis of the FBI, which he did.

(tense thoughtful music) - There's been a lot of study about why John Dillinger, you know, went into crime and became such a notorious criminal.

And it really stems from the fact that he was involved in a relatively minor robbery as a young man, and then they threw the book at him.

And when they threw the book at him, he went to prison for a long stretch of his young adulthood.

- There were a series of unfortunate developments in John Dillinger's life.

His mother died early, he got married early as a young man, and his wife divorced him, and then he robbed a grocery store.

He literally, in robbing the grocery store, stole $50 out of the cash register, out of the till.

He was immediately recognized.

You know, he didn't even have a mask over his face.

He didn't have a weapon.

He had a handkerchief with nuts and bolts in it as a weapon.

He was immediately arrested and got terrible advice.

"Don't hire a lawyer."

Oh, God.

So John Dillinger, young John Dillinger, was sent to one of the most brutal prisons in the Upper Midwest.

- It hardened him.

It really embittered him that he was in prison for such a long time.

He felt like it was unjust.

And once he got out, he was like, "I am not going to abide by society's norms.

They were not fair to me.

I'm not gonna be fair to them."

- And when Dillinger, young Johnny Dillinger, went into prison, he was a bad crook.

He couldn't even rob a grocery store.

He met members of the Dillinger Gang in prison, the future Dillinger Gang.

And they taught him.

Dillinger got a Ph.D.

in crime when he was in prison.

And as evidence, when Dillinger gets out of prison, he robs a police armory, starts robbing banks, gets arrested, escapes from an escape-proof jail in Crown Point.

Suddenly, the juvenile delinquent who went into prison came out John Dillinger, not a master criminal by any stretch, but a talented bank robber.

- John Dillinger was probably the best-known individual from this period of time.

And there's a couple of reasons for that.

One is that he was covered in the newspapers extensively.

The second thing is the reason they were covering him is because he kept escaping.

He had this uncanny ability to get out of a jam.

He did this in St.

Paul.

He did this in Little Bohemia up in Northern Wisconsin.

He did this when he escaped from a jail in Indiana.

Dillinger was caught in Arizona.

They wanted to prosecute him for a murder that had occurred in Indiana.

Dillinger was brought from Arizona to Indiana and placed in the Lake County Jail.

The reason they selected the Lake County Jail is, purportedly, it was a jail that he could not escape from.

And ironically, he shows up, and there are, famously, are pictures of him with his arm around the prosecutor, the district attorney, and the sheriff is there; it's a woman.

And everybody thinks this is gonna be great.

They're all gonna hang out and live happily ever after, until he's prosecuted and goes to prison for the murder.

Well, what happens is there's a whole plan hatched for Dillinger to escape.

A person associated with Dillinger's attorney has this wooden gun created, and it is secretly brought into the jail to Dillinger.

This gun looks like a real gun.

And so much so that he is let out of the jail.

And he is allowed then to retrieve real Thompson submachine guns.

And then he hops in the sheriff's personal vehicle, which is the best, fastest vehicle.

And he escapes across the state line into Illinois.

Dillinger boasted later about using a wooden gun to escape from a jail.

He kept the gun, ultimately gave it to his family in Indiana, who kept it for many years.

And we were fortunate enough to be able to acquire the gun to be part of the Mob Museum's collection.

Local law enforcement was having no luck dealing with John Dillinger and others because, you know, he'd rob a bank in Indiana, and then he'd hop in a fast car and go into Illinois, and the jurisdiction would change, and nobody could get him.

So the solution to that was to have a federal law enforcement agency that could cross state lines, that could pursue him in wherever he happened to be.

And the FBI was this fledgling federal agency that was trying to make a name for itself.

- The Bureau of Investigation in the 1920s did not have much power, did not have much funding.

Hoover realized if he turned John Dillinger, who provably killed only one person, a sheriff, and was really, in some ways, not a big threat to a lot of people, J. Edgar Hoover realized, "He could be my Moby Dick.

I'll be Ahab, and Dillinger could be my Moby Dick."

Because Hoover knew taking down organized crime, the mafia, was very difficult, taking down disorganized crime, like John Dillinger, was quite likely.

So the FBI published books about John Dillinger, the FBI did newsreels, movies, at the time.

J. Edgar Hoover wanted to leverage Dillinger's celebrity to build the FBI that we know today.

(lively piano music) Dillinger, you could say, fell in love (laughs) with Evelyn "Billie" Frechette, a Menominee Native American woman from Wisconsin.

I think he did have feelings for her, that didn't stop him from going to prostitutes in any city that he went to.

Why she chose to love John Dillinger, it's hard to know.

She talked about how when she went dancing with John, Dillinger had just gotten out of prison, and he was a terrible dancer.

And Billie asked him, "Why are you stepping on my feet?

You know, you're not dancing well, John."

And Dillinger apparently said, "I've been in prison for a couple of years; that's why I am a bad dancer."

She knew, Billie Frechette, that the man she loved was a bank robber, and she accepted it.

(tense thoughtful music) Dillinger went to St.

Paul because St.

Paul had the deal, the O'Connor system, the layover agreement.

Dillinger figured he'd be safe, and he would be safe from the police.

But the FBI were a different story.

They were independent; they were not corrupt, the way the St.

Paul Police were.

So Dillinger moved into apartment 303, third floor, you could still see it today, of the Lincoln Court Apartments near the corner of Grand and Lex.

And they had a kind of domesticity.

She liked to take John Dillinger to the movies.

She talked about his favorite movie, this is Public Enemy No.

1, was Walt Disney's "Three Little Pigs."

And specifically, John Dillinger and Billie went to a movie theater that was two blocks away at the corner of Grand and Lex.

Dillinger and Billie, knowing that he was a bank robber, didn't wanna be exposed too much.

Billie made sure that the blinds were always drawn in their apartment so no one could see him.

But still, Billie Frechette, Dillinger's girlfriend, did his laundry.

And she would go outside.

You could see the lawn today in front of their apartment building.

And she would hang up his clothes to dry.

She would have scarlet-red short-shorts.

She was a 19-year-old woman, apparently very pretty.

I talked to men who were boys at the time, and they remember, "Oh, my God, this beautiful woman is standing outside there."

And then the landlady, Daisy Coffey, noticed something was weird.

They would always get their mail only in the dark when no one could see them.

The shades were pulled down.

And then, of course, Billie Frechette was out there attracting unwanted attention.

So Daisy calls the FBI.

And the FBI and police, St.

Paul police, come to the Lincoln Court Apartments; they don't know who he is.

They get a report that there are suspicious individuals on the third floor of the Lincoln Court Apartment.

But in St.

Paul, to get a rumor that there was a "suspicious individual" in a city filled with gangsters was not unusual.

So they knock on the door.

Billie and John are in bed.

Billie, in her nightgown, pads to the door, opens it up a crack, sees the FBI.

They apparently go, "Ma'am, we need to speak to Carl Hellman."

Hellman is Dillinger's alias.

The dear woman, Billie Frechette, forgets her own alias.

"Hellman?

Hellman, that sounds vaguely familiar.

Oh, oh, my husband!

Yes, I'll- I'll go and get him."

And the FBI's going, "What's going on here?"

Billie races to the bed.

Dillinger is already putting on his pants.

He says, "Don't worry."

He reaches under the bed, takes out his weapons, says, "Be behind me.

We're gonna get through this.

And you know where the car is."

They had a getaway car, two buildings away.

Dillinger apparently kicks open the door, smiles at the cop and the FBI, and opens fire.

And the indication that John Dillinger was not a master criminal is not a single bullet from Dillinger's gun hits any of the lawmen.

But one bullet from the police officer, I believe, hits Dillinger in the thigh.

So he lays down fire, he grabs his girlfriend, Billie.

They race out the back.

Again, there's no one covering the back door because they didn't know it was John Dillinger.

They just figured it was some guy.

So Dillinger, bleeding like a stuck pig, is standing in the back, again, totally exposed.

And Dillinger gets away for some rest and relaxation in Rhinelander, Wisconsin, at Little Bohemia Lodge, escaping again.

It was very embarrassing for the FBI.

It was so humiliating for J. Edgar Hoover, the Society of American Magicians, gave John Dillinger its Harry Houdini Award for the escape from St.

Paul.

J. Edgar Hoover sent the word out, "Kill him.

Find Dillinger, kill him.

Then I'll interview him."

So, a shoot-to-kill order.

Well, it gets dark.

The FBI's been tipped off.

The woods around Little Bohemia are filled with FBI agents, just waiting.

A car putt-putts out of Little Bohemia.

They open fire and mortally wound a conservation worker.

It's not John Dillinger.

And worse, the accidental shooting of a non-Dillinger person alerts the Dillinger Gang: "Oh, my God, the shooting out there.

Let's get out of here."

The Dillinger Gang tells their women, "Stay here, we'll be back for you."

Yeah, right.

And the Dillinger Gang bursts out of Little Bohemia, and they race towards St.

Paul, which is where they will be safe.

Unfortunately, they kill an FBI agent in the process.

(gentle thoughtful music) When he went to Chicago, he decided to go to the movie theater.

It was "Manhattan Melodrama," perhaps the wrong movie to see because the criminal in the movie dies in the electric chair.

And Dillinger was accompanied by a brothel owner, who was the Woman in Red, and Polly Hamilton, a prostitute.

Apparently, a deal was struck between the FBI and a Chicago police officer and the Lady in Red.

And they said, "We will not deport you," She was about to be deported from America, "if you give us John Dillinger, Public Enemy No.

1."

Ultimately, they did deport her, but... Poor woman.

So Dillinger, with these two women, goes into the theater.

He watches the movie where the criminal dies.

He comes out of the movie theater.

And outside, the FBI are hiding behind trees.

They're hiding behind post office boxes, waiting for the signal to kill Dillinger.

The two women say, "Excuse me, we have to go back into the ladies' room."

And so the most wanted man in America is standing in front of the movie theater.

Apparently, Melvin Purvis, who is the head of the Chicago Bureau of the FBI, the signal to kill Dillinger was Melvin would put a cigarette in his mouth, take a cigarette lighter, light it, and then they would kill Dillinger.

Melvin was known after this, Melvin Purvis, as "Nervous Purvis" because Melvin couldn't get the lighter to light.

But eventually it did.

They closed in; they killed John Dillinger.

- I think the way that John Dillinger was killed in Chicago contributed to this idea that he was, you know, sort of this underworld hero.

He was shot in the back, and that there wasn't a confrontation that led to his death.

I definitely think that is part of the story that people cling to and say, "Look, you know, this was a guy who was, you know, certainly, you know, violence was part of what he was about, but he was someone who was one of us," right?

"And this imposing federal agency, the FBI, is a much less representative of the people than John Dillinger was."

- In death, Dillinger is elevated by pop culture, but if you look at the newsreels, you can tell he's working the camera.

- Yeah, another reason that John Dillinger became so well known and infamous was that he had this really engaging personality and was a jokester.

You know, people liked him, a very winning personality.

He had a lot of girlfriends, and he was very casual in his relations with law enforcement and with others.

He got along with people no matter who they were.

- There's a disturbing photograph of Dillinger, who's been arrested, and he's got his arms around the law enforcement guys.

And you could see... I mean, he was a relatively good-looking man.

You could see literally Dillinger looking at the lens.

So weirdly, I think Dillinger knew he was not long for this world.

He had friends who had already been shot to death by the police, and I think he knew immortality was behind the lens.

The legend is that 15,000 people walked by his corpse in the medical examiner's office.

Women dipped their petticoats in John Dillinger's blood in the street, which gives you a sense of the kind of infamous, notorious celebrity that John Dillinger had.

(lively upbeat jazz music) - We hope you enjoyed this episode, and if you wanna support us and our station, you can see more behind-the-scenes content and full-length, uncut sessions on our Patreon at Patreon.com/Missouri.