‘Greatest Escapes With Arturo Castro’ Episode 8: Dashing Dillinger

Mental Floss is partnering with FilmNation and iHeartPodcasts to bring you the transcripts for Greatest Escapes, a podcast hosted by Arturo Castro about some of the wildest escape stories across history. In this episode, Sunita Mani (Spirited, Glow) joins Arturo through a slew of gangster-riddled escapades as they peel back the pages of history surrounding the most “dashing” criminal of the 1930s: John Dillinger. Read all the transcripts here.

Arturo Castro: This is Greatest Escapes, a show bringing you the wildest true escape stories. Now, today we’re gonna go back to the Great Depression and to the golden age of the bank heist to tell you a story of a man who may be America’s most celebrated outlaw.

I’m Arturo Castro, and I’m joined by a fantastic actress, a super kind soul who always makes me want to get up and dance: Sunita Mani!

[THEME]

Arturo: Whoa, that was a Ben Chugg special. And everybody, we got a real treat for you today. I am such a big fan of her, and I’ve known her for a long, long time, I guess by this point. So welcome to the show, Sunita Mani. Gimme a brah-brah-pow!

Sunita Mani: Thank you. Brah-brah-pow! Hi, Arturo.

Arturo: Ben? Where is my brah-brah-pow?

Sunita: Oh.

Arturo: Ben?

[Airhorn sound]

Arturo: Thank you! But I—I love you for, for being like, “OK, I guess you just said yes to the dress.”

Sunita: I was too ready.

Arturo: We love you for that.

Sunita: I was too ready to provide the sound effect.

Sunita’s Escape

Arturo: So, on that note … What do you consider to be your greatest escape?

Sunita: Yeah. I was just thinking about the time that I feel like I escaped the jaws of death.

[Dramatic music]

Arturo: Whoa. Dramatic music. We’ll put it on in post. It’s gonna be so cool.

Sunita: It’s the first thing that came to mind. I was on my honeymoon with my now-husband in Italy. We were in Sicily. So this is like 2018, well before White Lotus.

Arturo: OK, 2018. You were there first. Mm-hmm.

Sunita: We had this, like, wonderful time, this, like, lovely week. The whole week we had been doing, like, really remote stuff, but this was like, a populated place. Anyway, we’re swimming in the ocean. It’s lovely. All of a sudden—we’re getting a little far away from the shore, and it’s, like, kind of, noticing no one … no one else is like, really in the water. Maybe we should go back. Let’s, let’s just—like, yeah. I don’t know. It feels a little far, so we’re trying to go back to the shore.

We cannot get back to the shore.

Arturo: And you feel like you’re not making progress.

Sunita: We are not making progress at all. It’s—it’s a riptide, I guess I had just never been caught in like a riptide before.

Arturo: Could you feel the current?

Sunita: Yeah. Yeah. I wasn’t, like, feeling like a swirling vortex or anything. We just, like, couldn’t swim out of it. And I—now, I know this, to anyone who is ever caught in a riptide, you don’t swim, like, directly towards the shore. You swim parallel to the shore now to get out, and it was, um, one of those guttural things of, like, screaming for help, where you’re just like, I don’t know—we don’t know what to do. And it was, like, far enough away that—the shore was—to not even know if anyone could hear us.

Arturo: Could you see people on the shore?

Sunita: Eventually we see these, like six men in Speedos run—race into the ocean, like to come after us. They’re like, yelling Italian at us.

Arturo: “Get closer! Riptide! Riptide!” And you’re like, “I know!”

Sunita: They’re calling us idiots. Like, “what were you thinking?” And we’re like, “I don’t know. Did we miss a sign?” I—I don’t—I don’t know. So we’re kind of, like, linked arms with these strangers who are nice enough to, like, try and help us.

Arturo: Mm-hmm.

Sunita: And then all six of us can’t get back to the shore.

Arturo: No.

Sunita: Or, well, eight of us, me and my husband in these, like six men in Speedos.

Arturo: Yeah, it was just six of us, cause the, the two of them died, but we’re now—don’t mention those at all. Wow. So now you’re all f***ed.

Sunita: Now we’re all screaming. We’re all f***ed. And that’s when they really start yelling at us like, “it’s your fault.”

Arturo: “I’m gonna f***ing die! This is not how I want to die!”

Sunita: By this point the, everyone on the beach is just like standing up and watching, and like looking out and being like, “uh oh, what’s gonna happen?” Finally, a lifeguard like comes to throw one of those like life rings, you know, and he’s gonna try to pull us in and we’re just like—again, the shore—the waves are really turbulent, so by the time it, like, the donut gets to us and we’re trying to meet the donut halfway, it’s like–

Arturo: Oh my god.

Sunita: –this struggle.

Arturo: You’re getting exhausted by this point.

Sunita: We’re so exhausted. We finally reach the damn donut and, uh, um, it’s connected to a rope so that they could, like, pull us in from the shore.

Arturo: Mm-hmm.

Sunita: They let go of the rope.

Arturo: Why the f*** would they let go of the f***ing rope, man?

Sunita: I don’t know what happened, but I think we were just too far out and they were like, “well, at least they have the donut.” So–

Arturo: One donut for f***ing eight people? What an Italian way to think of it: “Eh they—they have the donut now. They’ll figure it out. I did my job.”

Sunita: We’re all like–

Arturo: –and they all continued on with their day and they’re like, “OK, they’ll be fine.”

Sunita: And then eventually they like—because it’s a marina, someone—like someone in their, like little motorboat come from behind us—like, they don’t come from the shore. They actually, like, kind of come from behind because I think the waves are just too strong. So.

Arturo: The visuals of this are amazing. You have to write this.

Sunita: Yeah. So eventually we like do get on the boats and that’s when I started like really panicking actually. That’s like when I totally broke down, like when we were OK, I was like hyperventilating, like really sad and scared and–

Arturo: Yeah, of course! Oh my god, of course.

Sunita: They were so nice. We finally got back to the shore. It was such relief. But also I was like, OK. I guess we’re like drinking wine now at a another cafe or something. It was wonderful. It’s like that feeling of like, life is so beautiful and fine and lovely and I’m so grateful to be here and also like, wow–

Arturo: What the f***.

Sunita: I am paralyzed by, like, fear at the same time.

Arturo: Oh my god. Uh, well listen, thank you so much for sharing that. I’m so glad we—you are OK.

Sunita: Hey, thanks.

Arturo: And to the banana hammock gentleman of Sicily: grazie mille.

Sunita: Grazie mille.

Arturo: Mi amici. All right, well, are you ready to hear of another escape, Sunita?

Sunita: I’m so ready. Yes.

CHAPTER 1: Learning the Trade

Arturo: For today’s story, we’re headed to the American heartland, Indianapolis, and also, incidentally, the romance capital of the world to some.

Sunita: No.

Arturo: No, it is not.

Sunita: OK.

Arturo: Nobody, nobody there has ever thought–

Sunita: I refuse.

Arturo: So, not the romance capital of the world, Indianapolis, but in—the year that we’re talking about is the year 1903, and that’s when a boy named Johnny is born into a family that owned a grocery store. That’s—I know it sounds like random detail, but it’s gonna come up again. OK. So grocery-based crime, it’s gonna be on the way, OK?

So as he grew up, Johnny was constantly getting into trouble, and his dad, like many dads at the time, tried to punish the rebellion outta Johnny. Now, spoiler alert—it did not work. So Johnny got up to some mischief. He formed a neighborhood gang of kids who called themselves the Dirty Dozen.

Did you have a—did you have a tight group of friends when you were growing up?

Sunita: I was in, like, a little neighborhood gang and none of us went to school together. It was—it felt very much of the, like, the three blocks, you know, where we lived, and like, we shared a—I shared a backyard with one of them. And yeah, we had our li’l bikes and we would, like run around in the woods and–

Arturo: Oh, that’s so cool. So you didn’t commit any crimes with your neighborhood friends? Neither did I. But–

Sunita: I’m sure I did.

Arturo: “I’m sure.” [laughs] I’m sure something illegal went down. Oh yeah. The worst thing we did, we … we stole a stop sign one time cause we wanted to hang it on–

Sunita: We were little a**holes like that. Yeah.

Arturo: Yeah. We were like, “we’ve vandalized some sh*t, for sure.” So, sorry, Guatemalans, if you ever … Come get me! There’s no extradition laws.

So the crimes that Johnny committed with this Dirty Dozen gang were little things—like, the day they stole some liquor off a train and Johnny showed up at school drunk.

Sunita: Sounds fun. OK …

Arturo: Yeah. I was like, “Johnny, let’s hang out.” And then there’s a time they nicked some coal from railroad cars to sell to their neighbors.

Sunita: Wow. These are such old timey–

Arturo: Yeah, it’s like—so, yeah. “We have an ice box here. See? Yeah.”

Sunita: Distributing coal!

Arturo: Yeah, it’s kind of industrious, isn’t it? So most neighbors actually describe Johnny as a cheerful, likable youngster, and they said that he dressed well. And they thought he was only as mischievous as every other boy, right?

Sunita: OK. They gave him some slack. Got it.

Arturo: Yeah, they cut him some slack. “He dresses well, he gives us coal. F*** it!” So that’s all it took back then.

Sunita: Simpler times.

Arturo: Yeah, it was the romance capital of the world!

Sunita: Yeah. [laughs]

Arturo: F***in’ people were just, like, chilling. So in 1920, John’s dad moved the family out of the city to a small farm and he was trying to keep John out of trouble, but no dice. Like, John got extremely bored and he was always driving back into Indianapolis looking for something to do.

Sunita: It’s Johnny’s way.

Arturo: Yeah. Johnny, or get out of the way, you know? He wanted to see more of the world.

Was there ever any time growing up whether you had, uh, a real sense of wanderlust?

Sunita: Yeah, I think there was always like a small town girl, wide-eyed for the city, like syndrome that I had.

Arturo: You, you always had New York in your sights?

Sunita: Yeah, I mean I think it was like, watching Annie or something, you know? It was just having that—I don’t know, just like, wanting to be Annie.

Arturo: [laughs] Yeah, and you were, and call–

Sunita: Little orphan Annie in the city.

Arturo: Calling myself Annie was also—added to that effect. So once, when John was driving to the city to visit his girlfriend, who also happened to be his uncle’s stepdaughter—weird.

Sunita: OK. Got it. That’s like Clueless, right?

Arturo: Uh huh. It’s kind of Clueless. I don’t know.

Sunita: Like where like, like Alicia Silverstone’s character–

Arturo: That’s what it is. And Paul Rudd?

Sunita: –and Paul Rudd’s character. Yeah, they’re like–

Arturo: I take it all back it’s not weird, it’s Clueless-y.

Sunita: It’s Victorian.

Arturo: Yeah. And also it’s his uncle’s stepdaughter, so it’s even twice removed.

Sunita: Yeah.

Arturo: Fair game, buddy. So the thing was John was driving a car that he had stolen for the trip. So he ran from the–

Sunita: What?!

Arturo: Yep. He ran from this traffic stop and the cops actually fired a couple shots at him as he scampered away. And the whole situation was just generally a mess, you know? So John decided that his best way out was to skip town completely. So he did the logical thing, which you do at a time, and he joined the Navy.

Sunita: Hop on a train? Oh, OK. I’m—this is like, playing out like a Charlie Chaplin film or something in my head.

Arturo: Exactly, exactly. So he started—he learned how to tap dance and, yeah.

Sunita: Hey. Yeah. The car’s swerving. Yeah. And the shots are firing–

Arturo: “Hey, get up on it. Pew pew,” and just like, a little chyron that says “pew pew.”

So John served on this ship for only a few months. He thought that his dad was harsh, but now that he was a fireman in the Navy—meaning that he shoveled coal into the engine furnaces–

Sunita: Oh, the coal!

Arturo: The coal, not the coal! It f***ing sucked. So John naturally went AWOL and the Navy placed a bounty on his head: $50 for the runaway fireman.

Sunita: OK. $50 must have been a lot back then.

Arturo: $700,000 at the time.

Sunita: Well, yeah. Great.

Arturo: It was actually where you could buy a country with $50. It was the first time the authorities offered money for his capture, but it was far, far from being the last. And apparently the Navy wasn’t looking too hard for him. They’re just kinda like, “if it’s no trouble, if you find him on the way.”

Sunita: This is like how I dog sat one time in LA and the owner was like, kind of joking about like, “if the dog like, you know, runs away, it’s like—it’s all right.”

Arturo: “There’s like an insurance thing, don’t worry about it.”

Sunita: “No, we don’t like the dog very much actually. I mean, my kids really like the dog, but if something happens to the dog, you know, honestly it’s OK.”

Arturo: “I won’t ask questions.”

Sunita: Like it’s—truly–

Arturo: Oh my God.

Sunita: I wasn’t sure if he was like, trying to tell me to, like–-

Arturo: Like, “am I involved with a psychopath?” So listen—so since the Navy wasn’t really looking too hard, John actually showed up back home and he was able to pass it off to his family, that he had been honorably discharged, he spent a couple of months playing pool and baseball and sweet talking a teenage girl.

Sunita: Wow.

Arturo: John was 20 and he married a 16-year-old who moved in with his family. Which, gross? I don’t know. I’m firmly on the side of no minors marrying.

Sunita: I can’t tell if this is just like—is this regular confidence that people had back then? Like there’s—are there a lot of Johnnys like this? I don’t know. I feel like you could get away with all this sh*t for a long time.

Arturo: That’s what—that’s the Industrial Revolution, uh, children, you know. So things took a darker turn in the fall when John and a friend robbed a grocery store.

Sunita: Mm.

Arturo: Yeah. The grocer locked up the store at the end of the week and was walking home with the money from his cash register. When John jumped him. He attacked the man with an iron bar—that’s f***ed up—and John was arrested for the attack. His dad was so pissed. He—he actually advised John to plead guilty and take his punishment for the crime cause he thought that since this was John’s first arrest, that he might get off easy.

Sunita: Lol.

Arturo: No, no, no. John Johnny … Young Johnny was given the maximum penalty of 10 years in prison even though he had no previous criminal record.

Sunita: Well, it’s making up for all the bad sh*t he did.

Arturo: So, for 10 years John stewed in prison, rubbing shoulders with other social outcasts, and as it turned out, he kind of fit in.

Sunita: Oh my goodness.

Arturo: So like him, they weren’t suited for the discipline of Navy ships or backbreaking farm work, or semi-professional Pilates. Uh—I don’t know what the f*** they were doing at the time. They were burglars, bootleggers, and train robbers, and John Dillinger was taking lessons.

Sunita: Buh—what?

Arturo: You know the story of John Dillinger?

Sunita: I have heard of him, but I’m like, forgetting history.

Arturo: I got you. I got you.

Sunita: A-thank you.

CHAPTER 2: Grocery Burglar

Arturo: One defining trait of John Dillinger was his love for looking good. Think Paul Rudd—he’s just like, ageless, forever. When he made it out on parole in May 1933, he was ready to go out there and get himself a straw boater hat, a fresh haircut, and a silk cravat or two.

What’s a cravat—like a cravat? Like, a little—little tie?

Sunita: A cravat is like a neck handkerchief?

Arturo: Is that what it is?

Carl: That is correct. A nice little neck tie.

Arturo: Ooh. I want one.

Sunita: Mm, it sounds delicious.

Arturo: As one historian was very careful to note, John came outta prison, smarter, trimmer and more muscular, which made him, and I quote–

Sunita: Hold on.

Arturo: Yeah. And I quote, “attractive to women and respected by men,” which sounds–

Sunita: It’s in history! That is written in history as true.

Arturo: It sounds like a hilarious commercial, right? But like, for prison.

Sunita: For prison. Exactly.

Arturo: Gimme a light ad music.

Ben: Alright. We haven’t rehearsed this—here we go.

[Light ad music]

Arturo: “Hi. Are you a loner who hates the Navy? Did you get compared to the shrimp you sell at your dad’s grocery store? Then you need the one and only all-inclusive stay guaranteed make you smarter, trimmer, more muscular. Prison. Become attractive to women and respected by men. This message is brought to you by Dapper & Swole Private Incarcerators LLC.”

Sunita: Wow!

Arturo: Ah, not bad for our first try at that! That’s great. But John stepped outta prison into hard times, right? The banks had crashed in 1929 and it was the Great Depression. So yeah, there weren’t a lot of jobs for an ex-con stepping outta prison, no matter how f***ing sexy he looked, apparently.

Sunita: Aw sh*t. Aw.

Arturo: F***ing sexy, bro. “Bro—you’re looking good, bro.” I love a historian being like, “bro, I gotta tell you, you’re looking f***ing good.”

So this was no problem for John though, you know, because he didn’t even try. First he went home and he told his family that he had learned his lesson. He was a new man.

Sunita: He is a liar.

Arturo: He’s a f***ing liar.

Sunita: He’s a f***ing liar.

Arturo: The second thing he did? Sunita, he met up with a bunch of guys who knew his prison buddies and they struck up a plan.

Sunita: Of course.

Arturo: This was the beginning of what one historian calls “John Dillinger’s Wild Ride,” one of the most buck wild crime sprees in American history.

Sunita: Dear Lord.

Arturo: Yeah. No, it was wild. So they kicked things off with a couple of starter robberies—uh, just, like, to get their feet wet.

Sunita: Just some teasers. Mm-hmm.

Arturo: That’s right, appetizers, if you will. Uh, cravats—a cravat.

Sunita: Cravats.

Arturo: A little cravat for the hunger. Um, so they hit up two grocery stores. That was just to prime the pump a little bit. Right?

Sunita: OK.

Arturo: Then it was onto the real targets.

In June 1933, John rolled into New Carlisle, Ohio, the second romance capital of the world, and together with his new gang, he was headed for the National Bank. Word on the street was that they always left the rear window open in the bathroom even at night, which to me sounds like an inside job. How would you know?

Sunita: Uh, yeah.

Arturo: Unless they were putting it like—that was like, their sh*tty slogan, like, “come to our bank, the windows are open anytime. Um, our door’s always open—even if it’s not, our window is in the back.”

Sunita: Because people will be taking huge sh*ts in the bank, I guess?

Arturo: That’s what—they just get nervous, depositing all this money.

Sunita: Yeah.

Arturo: Word on the street was correct. John and his gang crawled in through the bathroom window under the cover of darkness. And they walked right out cause it smelled like sh*t.

Sunita: Yeah.

Arturo: They were like, “I don’t—I can’t hang.”

Sunita: “Not worth it.”

Arturo: They—they laid down behind the counter and waited until the morning when the staff came in to open the bank.

Sunita: Oh my God.

Arturo: Yeah—for a second I thought that where this was going was like—and then they just kind of had—have had at it, you know. They were just like—had the run of the bank.

Sunita: Right in the dark. Yeah. In the shield of like night.

Arturo: No, no, no. They—it was way more elaborate than—or way more violent, I guess. As they came in one by one, John and his team grabbed them and tied ’em up at gunpoint. The youngest member of Johnny’s gang was only 19, and his strongest memory of the heist was how big John Dillinger’s gun was.

Sunita: OK.

Arturo: And how just trim and beastly and masculine he seemed. And also this, this 19-year-old was the one that went on to be a journalist and write into history how hot he was—no.

Um, so eventually John forced the staff to open the vault and walked out with $13,000, which is like $300,000 in cash today.

Sunita: That’s—that’s a lot. I mean, f***.

Arturo: It was, yeah, for—especially for these young, young whipper snappers. I guess he must have been like 30 by this point, but it wasn’t just a kid who was impressed. One of the local papers called it “one of the most cleverly executed crimes in the country’s history.” Journalists really f***ing love this guy.

Sunita: It’s like waiting for like, the review of your performance and as like, an actor or something. But–

Arturo: Yeah. You’re like … you’re—yeah. You’re waiting for The Hollywood Reporter.

Sunita: Expected entry, quite an expected premise of going through the window that we all know is open, but the real twist–

Arturo: Isn’t that the f***ing thing? Once—that once your show is out or whatever, you’re just like—I’m not one of those people that doesn’t read the reviews. I am like a hundred percent in there.

Do you skip ’em or do you read ’em?

Sunita: I have like a window where I’m like, “oh, I just have to, you know, I have to know.” The morbid curiosity. And then I—I feel like I don’t keep going.

Arturo: Well, funny enough, you mentioned it, cause we have the review of each one of your shows. Come on out guys.

Sunita: OK.

Arturo: As sung by the Vienna Boys Choir. Come on now. Um, so it’s gonna–

Sunita [singing]: “Not as good as her co-star!” [laughs]

Arturo: So after the newspapers were really kissing his ass, the bank employees actually remember that the other robbers all seemed crazed or high, and they were all extremely nervous and jumpy with their eyes bugging out. But not John Dillinger. No no.

Sunita: This guy’s a psychopath, right.

Arturo: No, he was apparently very calm. Yes, psychopath.

Sunita: And beautiful.

Arturo: Oh, and gorgeous. Apparently he was very calm and just—God, just like it was just—he was just bulging out of his pants. Um, he was polite through the entire thing, is what they said.

Sunita: OK.

Arturo: But it turns out that money wasn’t enough for John Dillinger. The very same day, the very same f***ing day when they got back to Indianapolis, John and his accomplices robbed—you f***ing guessed it—a grocery store. Bree bree bree!

Sunita: Ooh!

CHAPTER 3: Jackrabbit

Arturo: So the spree has sprung. John Dillinger and his crew set about robbing five Indiana and Ohio banks in four months. And John started to gain real fame as the bold, polite, absolutely f***ing sexy, dressed to kill—no, but literally they said, “dressed-to-kill burglar with a big gun.” Literally, they said that.

Sunita: The cops—I mean, people just want him to keep going, really. Like they—they can’t catch this guy.

Arturo: They’re—they’re like putting out ads in the newspaper, like, “don’t rob my bank.” You know?

Sunita: Yeah—“please, Daddy, no.”

Arturo: And then–

Sunita: “Our money is shiny. Don’t take it.”

Arturo: “Oh my God. Does the door not close proper? Whoa, what are we gonna do?”

So the next few scores were all in the same area, and Dillinger was cruising. In July, he hit that commercial bank in Daleville, Indiana, and made off with $3500. He hit two banks in August, one in Indiana and one in Ohio, and together they scored over $12,000.

Sunita: OK. What do you think he’s doing with this money?

Arturo: Buying amazing clothes. I don’t know what you’re doing with—buying cravats. I don’t know what you’re doing.

Sunita: Cravat collection. Right.

Arturo: Um, then they were back in Indianapolis for their biggest heist yet: $21,000, but by now they had a routine, yeah.

Sunita: Yeah. We know he’s coming. Yeah.

Arturo: By now everybody’s like—nobody’s like ramping up security or anything. They’re just like, “he’s not—I think he’s done, you guys, this man is satisfied.” No, no. His routine was set, you know.

Sunita: Yeah.

Arturo: It was: two men went into the bank while a getaway driver waited outside in the car. Dillinger ran forward, jumped the counter, and held the bank teller at gunpoint, forced them to open the cash drawers in the bank vault, and forcing them to fill the bags with money. He and his accomplice would walk right back out the front, hop in the car, and drive off. They were super fast, and the whole thing was over in minutes.

Sunita: It was happening, broad daylight, of course.

Arturo: They were gone before help could arrive. Did you know robbing a bank was gonna be this easy?

Sunita: No. It’s almost like … I wanna try it.

Arturo: Yeah, it’s almost like, “what are you doing this weekend?” All right, so John knew how to thank his friends for robbery lessons. He started sending pistols into their prison. Seriously sometimes he even just walked up to the jail and threw the guns over the wall.

Sunita: OK.

Arturo: But he would also pack them in these–

Sunita: That’s in the history books?

Arturo: That’s in the history books. He did not give a—like, yeah, he is—if “I don’t give a f***” was a person, it’s this motherf***er.

Sunita: Seriously.

Arturo: But he would also pack them in boxes of spoons and send them into the prison workshops. And how did they use their guns, you might ask?

Dillinger’s criminal cronies were now packing. They all teamed up. They rushed the guards, they moved through the halls and captured the superintendent. With their hostage in hand, they made their way outside to steal a couple of cars, but now bullets were flying. Blood is spilled, the cars peeled away, and the boys were out of there. The boys who had taught John Dillinger everything he knew were now on the loose.

But now, ironically, it was just like—that’s an impossible voice to do. I couldn’t do it for longer than that. But isn’t that wild?

Sunita: Yes.

Arturo: Ironically, it was just after his friends escaped that Dillinger finally got caught. After five bank robberies and God knows how many poor grocery stores–

Sunita: Yeah.

Arturo: –the cops had finally paid enough bribes to snitches and sex workers to find out where John’s girlfriend lived. And now we know what he was using the money for. And they staked out her boarding house in Chicago, which I’m like, “why don’t you just buy her an apartment with all this money, you f***ing asshole?” So one night, when Dillinger dropped by, the cops swooped in and just like that: The dashing bank robber was arrested.

Sunita: Wow. At his, like, girlfriend’s house.

Arturo: Yeah. And he was—like, he was already fully clothed and expecting them. No, I don’t know. Uh, and there was cravats everywhere. It feels almost too easy, right?

Sunita: It does. And—but at the same time, he just like, kept coming back to where he came from, too. Like–

Arturo: He did not—he was like, he got cocky.

Sunita: Uh, yeah.

Arturo: While John awaited trial, the papers started printing that the jackrabbit that jumped over bank counters was finally caught. But John was only in jail for a month. As soon as John was in, his whole gang’s mission became getting him out.

Sunita: Oh my God.

CHAPTER 4: Can’t Hold Him

Arturo: So Dillinger was being held at the Allen County Jail in Lima, Ohio. The cops had sent him there because they were worried that he knew how to get out of state prisons in Indiana.

Sunita: Sure.

Arturo: He had the maps of prisons and he also helped his boys get away already, but they moved him only one state over—like literally, it was just like a couple miles out.

Sunita: Right.

Arturo: So the–

Sunita: A completely unknown territory!

Arturo: Yes, of Ohio, where he’s also already hit banks. So the breakout actually happened on October 12, 1933. Six men gathered at the courthouse. Three men stayed outside, and three went in. Inside, they found the sheriff sitting at his desk reading the newspaper while his wife sat nearby working on a crossword. OK. What a detail to keep in the history books.

Sunita: Seriously. It really is like scenes from a Chaplin movie or something—like, every little detail that that feels like, uh–

Arturo: It gets better. The deputy was sleeping on the office couch too, I swear to you.

Sunita: Oh my God. That’s all we were missing.

Arturo: And the men told the sheriff that they were officers who needed to question Dillinger.

Sunita: Lol.

Arturo: When he asked to see their credentials, they pulled out their pistols. The lead man said, “here are our credentials, buddy. Hey, here’s our credentials, see?” And they gunned down the sheriff where he sat.

Sunita: God.

Arturo: After he was shot, they beat the sheriff until his wife broke down and gave them the keys. Also, don’t you think that like—getting shot is enough to like, give over the keys?

Sunita: Get the keys from—yeah. And it—it is shocking that there’s just like no protection of—like, at all, from this thing happening.

Arturo: And how does the wife have the keys, man?

They grabbed her and they dragged her to the cell along with the drowsy deputy. They put her in when they pulled Dillinger out. So the gang ran outside, and they piled into two waiting cars and they hit the road.

Sunita: Wow.

Arturo: Two days later—this is so wild—they hit a police station at a little town north of Fort Wayne, Indiana. They swarmed inside with guns drawn, locked up the cops, and scooped up their arsenal. Two automatic rifles, a Thompson submachine gun, three bulletproof vests, and all the ammo they could hire. Can you believe?

Sunita: This is insane.

Arturo: Can you believe? And that was only their first stop. You would think that maybe the police stations might be on alert at this point.

Sunita: Right? Right.

Arturo: But no, no, no. And apparently not in Peru, Indiana, no.

Sunita: Everyone is so indefensible. It’s like—it’s so wild. There are no consequences.

Arturo: Yeah.

Sunita: Yeah. Is he done? Get outta here!

Arturo: A week later, they hit the police station in Peru, Indiana, and they locked up all the cops in the basement. They collected their weapons with two more Tommy guns, a couple of shotguns, more body armor, and so many rifles and pistols that it’s really not even worth listing them.

Sunita: Wow.

Arturo: Leaving bodies in his wake now, Dillinger was free and armed to the teeth, so his gang got immediately back on their horse, hitting banks across the Midwest.

Sunita: Wow.

Arturo: At one bank—this is also f***ing crazy—where the cops actually caught up with him, Dillinger marched right out the front door with a human shield. The man jumped out of the way and the police opened fire. But Dillinger was armored up, right?

Sunita: Oh god, yeah.

Arturo: Witnesses said that bullets just splashed off his chest.

Sunita: Ew, my God.

Arturo: Like if they, if—if as if the newspaper people needed more reason to be thirsty for this guy, right?

Sunita: Exactly. He is invincible!

Arturo: It was like a Superman before a Superman sort of thing.

Sunita: Exactly.

Arturo: It’s like, “Oh my God, he’s made of steel!”

So the cop was shot eight times and Dillinger’s accomplice was also hit, but the robbers still managed to make a getaway despite the rain of bullets slamming into their car.

Sunita: So much gun—like battle. It’s wild.

Arturo: So much gunplay you guys.

Sunita: Yah.

CHAPTER 5: Lock Him Up

Arturo: As the news came in of bank after bank getting turned over by Dillinger’s high-powered gang, the National Guard started talking about sending in tanks, planes, and even loads of poison gas to Indiana to try to stop him.

Sunita: One guy.

Arturo: What do you think their f***ing plan was, like–

Sunita: What?

Arturo: –were they gonna go like, gas the whole state?

Sunita: Right.

Arturo: “We’re, like, we’re gonna—we’re gonna kill a bunch of people, but we’re definitely maybe gonna get him too.”

Sunita: “One of ‘em is probably gonna be John Dillinger.”

Arturo: They couldn’t stop Dillinger. At one point, he even mailed a little present to the chief of Indiana State Police: a book called How to Be a Detective. Oh, f***ing trolled buddy. [Airhorn sound] You got punked!

Sunita: Wow, dude. This guy is so psychotic.

Arturo: Um, the gang robbed Banks in Indiana, Wisconsin, and Illinois. When it was all told, they were hauling close to $3 million in today’s money.

Sunita: Man, I mean, maybe supporting the sex work economy of 1933.

Arturo: Single-handedly propping it up–

Sunita: Yes.

Arturo: –with their bank hauls.

Sunita: Sure.

Arturo: With that huge score in tow, they packed up and ducked outta sight. They went to a place where everyone brings their ill-gotten gains. They went to Florida.

Sunita: Oh, right baby.

Arturo: Yeah. So they slipped outta sight while the National Guard was mobilizing. Eventually, there were shotgun gangs and machine gun squads of National Guard troops setting up checkpoints on the highways across the Midwest. But Dillinger was already out of reach–

Sunita: Way down south.

Arturo: –and he had adopted a Cuban accent. He was talking a little bit like this, like, “I don’t know, [speaking Spanish]”—you know, that’s why they couldn’t find him. And everybody in Florida found him incredibly sexually attractive.

Sunita: Oh my God. Get–

Arturo: No, I’m joking. I don’t know, but they probably did. Um, he found a hiding place in Florida. He and his gang spent their time playing cards, swimming, fishing, drinking, and hanging out.

Sunita: Unreal.

Arturo: But Dillinger was too restless to relax. Yes. He was—just enjoy your vacation, John. Like, why do people never—I don’t know.

Sunita: You did it. You made it out.

Arturo: Yeah. Are you a person, when you’re not—trying not to drown in your vacation, are you a person that … are you—do you get angsty, or are you good with chilling for a while?

Sunita: I need—I need those moments. Yes. I like have those vacations or—or whatever … retreats, whatever, so that I can just be there, cause I love it. I love to just throw my feet up.

Arturo: When we were all starting out and there were like, periods of like, enfor—like of involuntary resting, like—I was never good at that.

Sunita: Right. No, that’s true.

Arturo: I was hitting up every Craiglist audition, every f***ing Backstage, Actors Access, Mandy.com. I–

Sunita: Right. No, it’s true. Downtime can feel like you—you’re just, like, drowning. But when it—I guess I … I feel lucky.

Arturo: When you earn the pause. When you earn the pause, that’s f***ing fantastic.

Sunita: Yeah.

Arturo: So in the end, it wasn’t the National Guard who put the clamps on him. No, no. It was the local police in Tucson, Arizona.

Sunita: Leave it to Florida. Oh, wait. In Arizona now? Not–

Arturo: Yeah. Yeah. Yeah. Arizona caught him. As the Dillinger gang was planning an escape route to Mexico–

Sunita: Of course.

Arturo: –some of the John’s pals got drunk at a local bar and started bragging, as everybody f***ing does.

Sunita: Yeah.

Arturo: Cops got wind of it and they raided the house where the gang was staying and scooped up a lot of the weapons and gear, arrested the people inside, and then they just waited.

Sunita: Oooh.

Arturo: Dillinger pulled up a few hours later, he walked up the steps and right into a police ambush.

Sunita: Oh. Just as he was loosening his cravat.

Arturo: Yes. He was pouring himself his first tumbler of brandy. “Have you people no shame?” Um, yeah, that’s, that’s how they caught him. And along with John and most of the gang, the cops grabbed up tons of new clothes in a house … It sounds odd for the cops to be thrift shopping from the thieves like that, but whatever.

Sunita: It’s like it’s just gonna go into evidence anyway. They may as well just, yeah.

Arturo: All these cravats are not going to waste. Uh, we better be sponsored by a f***ing cravat company after all this plugging. But what they had actually found was that, the clothes had been lined with money. That was it. It was the secret stash–

Sunita: Oh, my!

­Arturo: –for the gang’s getaway to Mexico.

Sunita: OK.

Arturo: Yeah. That one really shocked you, huh?

Sunita: I just—I like love the visual of that, like putting, um–

Arturo: I know.

Sunita:–like dollar bills under, like, a sewing machine and like, sewing them into a suit jacket or something.

Arturo: It’s so cinematic, isn’t it?

Sunita: Good idea.

CHAPTER 6: Flipping the Script

Arturo: That brings us to January 25, 1934. John Dillinger was shipped back to Indiana and locked in Crown Point jail to await his trial. Tons of armed guards marched around the jail for the newspapers to snap pictures of [him]. There was no way he was gonna escape this time.

Sunita: No.

Arturo: The trial was set for March 12, but Dillinger never planned to face the music.

Sunita: Wow.

Arturo: In his cell—and this is crazy, right—John used a razor to slowly carve out a piece of wood into a fake pistol.

Sunita: Oh my God.

Arturo: Then he blackened it with shoe polish and waited for his chance.

Sunita: Oh God. Getting shoe polish on the—the black market.

Arturo: Also—also like it’s all over your fingers now. It’s just gonna look gross, but like, you can never get that stuff off.

Sunita: Seems a little obvious. Yeah.

Arturo: So on the morning of Saturday, March 3, he was taken to the jail’s exercise room and left to himself. Nobody wanted to see him work out, apparently. He made all the craziest sounds.

Sunita: They don’t wanna see how the sausage is made. They just wanna admire.

Arturo: They’re like, “come out looking hot, dude.” Um, he called out to one of the jailers who came into the room alone. John stepped up behind him and stuck the gun in his back. He marched the man to the cells, locked in the jailer. Then one by one he was able to track down the other guards and lock them up, releasing another inmate along the way.

Sunita: It just—everything you’ve said about how he has just sort of gone in through the front door or just like–

Arturo: He’s just–

Sunita: –killed someone to get the keys or whatever. It’s just like, how is this …

Arturo: He finished the crossword puzzle to get the keys from the wife. Apparently, and this is the bananas part of the story, the prisoners were able to lure in two dozen prison officers and lock them up in the cells.

Sunita: It—yeah. It seems like he has like power—mind control powers or something.

Arturo: Yeah—“do you want to come here and listen to some jazz and then smoke some devil’s lettuce?” You’re like, “yeah, I’ll f***ing do that.” Um, John took one hostage—the county’s deputy sheriff—marched him to the prison locker, then popped it open and pulled out all the guns and gear. Then John and the other escapee walked across the street to the city’s garage. They waved the gun at the mechanic and asked for the fastest car. He pointed them to the sheriff’s 1933 Ford V8.

Sunita: Hilarious. The sheriff’s car.

Arturo: Yeah, and the mechanic remembered that Dillinger laughed when he realized it was the sheriff’s car.

Sunita: Yeah.

John pointed the Tommy gun at the sheriff’s deputy and forced him to speed off down the road towards Chicago. “Chicago or bust baby. Grab it on.”

CHAPTER 7: Silver Screen

Arturo: So more bank robberies followed with new confederates, like his new link with maybe the most memorably named gangster of the era: Baby Face Nelson.

Sunita: Wow. Adorable.

Arturo: He was just like, so cute and like, vicious. Between a South Dakota bank and an Iowa Bank they hit that March, Dillinger came away with another $2 million. So it was an early birthday present for John. On June 22, he turned 31, and on that day he was declared–

Sunita: Accomplished so much so young.

Arturo: Yeah. An overachiever. He was declared America’s first ever Public Enemy No. 1.

Sunita: That’s right. That’s how I know him.

Arturo: That’s how I know him.

Sunita: That’s where I’ve heard his name before. Yeah, yeah, yeah, yeah.

Arturo: And the government started throwing cash around—$5000 for information leading to his arrest. Or you could get $10,000 if you managed to capture him yourself. So that’s like, $200,000 in today’s money.

Is there—is there a time in your life where you might have been tempted to go after him?

Sunita: What’s the point? You’re gonna die. Yeah.

Arturo: F*** no! I don’t know what would make me chase down a dude that’s obviously like killed so many people and stuck up so many f***ing police stations.

Sunita: I know, right? That’s just … uh, they—it’s like they kind of … they need all the help they can get. It’s just a desperate, like, “uh, we’re gonna get ‘em. Or you could get ‘em if—if you can, could you please?”

Arturo: They’re like, “we’re gonna get him. But if you get to it first, I don’t know, like whatever.” Are you ready for a little more thirst?

Sunita: Oh, gimme.

Arturo: This was the point of when theaters were playing the news before the movies, and as the story goes, when the reels would play in the theater and Dillinger appeared on the screen, the audience would cheer. And you know who f***ing hated this? The head of the government’s Department of Investigation, J. Edgar Hoover.

Sunita: That’s right.

Arturo: OK. A little bit of trivia.

Sunita: That’s right.

Arturo: They had to rebrand because they got kicked in the balls so hard by Dillinger. Can you believe? Like that the Department of Investigation, like—he completely destroyed him in the PR battle, you know? So after just one year, they changed their name from the Department of Investigation to the FBI.

Sunita: Yeah. Rebrand.

Arturo: It kind of makes sense that people at the time were—were on Dillinger’s side, cause this is—I’m not condoning violence or robbery, of course (yes I am). But this is smack in the middle of the Great Depression.

Sunita: Right.

Arturo: So basically, what people know is that banks f***ing suck, the government sucks, and their lives were ruined by sh*tbags monkeying around with money beyond their control. Banks weren’t loaning anyone money for the things that they needed. You wanted to buy a house. If you wanted to start a business, then f***ing tough, like you weren’t gonna get any of the money. So Dillinger became kind of their fantasy. The bank refused you the money? What if we just walked in and took it?

Sunita: He’s the revenge fantasy. Totally.

Arturo: Exactly. So during the early robberies, one letter to the Indianapolis Star said,

Tory: “I’m for John Dillinger. See, he wasn’t any worse than the bankers or the politicians who took the poor people’s money. See, he didn’t rob poor people. See, he robbed those who became rich by robbing the poor. See?”

Arturo: Thank you very much. That’s a producer. Tory, everybody!

Tory: Thank you, see?

Arturo: But what really made him Robin Hood to the American people was the mortgages, because when his gang would rob a bank, they wouldn’t just take the money. They would also take the mortgage records and the title deeds that the banks held, and Dillinger would torch them.

Suddenly, the banks didn’t have the paperwork they needed to claim ownership over people’s houses. It wasn’t exactly stealing from the rich to give to the poor, but it was pretty f***ing close.

Sunita: Oh wow. Interesting.

Arturo: Yeah. And the stealing from the rich part he really had down pat. That was enough for a lot of people in the Great Depression, just to f*** up the rich people’s day.

Sunita: Mm.

Arturo: At this point, Dillinger was so popular and his mugshots were everywhere. He realized that he needed to change his look. It was too sexy, some people said. So, if you’re Dillinger and you gotta change up the look, what are you gonna do? Are you gonna get some killer sideburns or some mutton chops? What?

Sunita: You gonna go blonde?

Arturo: What would you do?

Sunita: Oh me. Ooh. Mutton chops sounds good.

Arturo: Yeah, right?!

Sunita: I really like style reinventions, like, to change up the—the exterior, I don’t know, like, hair, whatever.

Arturo: What if he just changed, changed the color palettes–

Sunita: But like–

Arturo: –that he uses. He’s like, “I’m gonna try more blues cause I’m feeling adventurous.” John decided plastic surgery was the way to go.

Sunita: What?

Arturo:  Ooh. F***ing risky

Sunita: Possible in 1930-whatever?

Arturo: Yeah it was.

Sunita: Damn.

Arturo: You know, a lot of advancements, uh, from plastic surgery happened because of, uh, people mangled in World War I. And so, to replace faces and to–

Sunita: Right.

Arturo: So a lot of the–uh, you know, they did really sort of crazy sh*t with, with very limited technology at the time. So—but … but John didn’t go the full route. He had two moles cut off. He sliced off a scar on his lip, and he pushed his cheeks higher. He had a dent in his nose filled in, but most importantly, he filled the dimple on his chin.

Sunita: What?

Arturo: Yeah, it’s a little limerick. On top of that, he had his fingerprints burned off with acid.

Sunita: OK.

Arturo: Ooh. Also, that’s a f***ing, like—I didn’t know that you could go that elaborate with, uh, plastic surgery at the time I thought it was really rudimentary.

Sunita: If you pay the right surgeon …

Arturo: But–

Sunita: Oh, you mean like—just everything, like filling in dimples and getting like a reverse buccal fat transfer? Yeah.

Arturo: Yeah, well, no, particularly the—the push his cheeks higher. It just seems like that—that feels like really complicated to do. I don’t f***ing know, but–

Sunita: Yeah that’s like breaking your face.

Arturo: He must look f***ing wild, dude.

Sunita: Yeah. Was he in like, a face brace? I mean, how do you like, heal–

Arturo: He had to–

Sunita: –from all that sh*t?

Arturo: Um, well, emotionally, we don’t know, but physically, three months. All—and this is all for the low, low price of like $100,000 in today’s money. That was not too bad. Oh my god. What the f***.

Sunita: Just like sewn into his–

Arturo: Cutting corners, man. That is some cutting corner sh*t. I bet you they gave him like, f***, pig slab on his cheeks.

Sunita: Ooh.

Arturo: Afterwards, he was hanging out at a friend’s house, lying low for a month, or actually not exactly lying low. After the surgery, John apparently thought he was untouchable, so he spent the month hanging out with his girlfriend all around Chicago. They went to restaurants–

Sunita: Oh! They’re still together. Even though she turned his ass in.

Arturo: It might have been a new one. I don’t know.

Sunita: Maybe new one. Maybe new one. Wait, so he did this facial reconstruction to disguise himself or just as a vain project?

Arturo: To disguise himself, yes.

Sunita: OK. OK. That’s what I thought.

Arturo: And he was just, he didn’t give a f***. He was, like, going to restaurants, amusement parks. John went gambling and he went to shows. Can you imagine, you’re like, at a f***ing like Death Cab For Cutie concert. You’re like, “is that the—no, it can’t be, um–“

Sunita: “He looks like, uh … Public Enemy No. 1?”

Arturo: I love that people would be like, “no, no, he’s got a chin dimple.”

Sunita: Yeah, right.

Arturo: So in true cinematic fashion, it was a trip to the movies that finally got John caught.

Sunita: Of course.

Arturo: So, one night a brothel madam who knew John’s girlfriend, told the cops that she was gonna join John for a movie at the Biograph Theater. They were watching a gangster flick, naturally, called Manhattan Melodrama.

Sunita: Meta.

Arturo: The movie ended just after 10 o’clock that night. When Dillinger stepped out of the theater with the crowd, some freshly branded FBI agents moved in.

Sunita: Freshly branded!

Arturo: Freshly branded.

Sunita: Wow.

Arturo: As the crowd on the sidewalk thinned out, Dillinger looked around and realized the agents were surrounding him. He bolted for an alleyway, but they didn’t chase. They just drew their guns and opened fire. This time John couldn’t outrun the bullets. A killer shot hit him in the back of the head and he went down.

Sunita: Wow.

Arturo: After he died, something like 15,000 people came to see his body and the legends about him continued. Of course, that included the story that he wasn’t actually killed at the theater. Some people said that his body was misidentified. And that the murdered man … was someone else.

Sunita: Oh, because of the cheeks!

Arturo: Yeah, probably. There’s even the idea that Dillinger allies actually hoaxed the investigators, that his girlfriend set up the cops with someone else, and that the FBI were tricked into gunning down some other man, which left Dillinger free to disappear. But the new FBI had no doubt. The acid burn hadn’t worked. And Dillinger’s trigger finger was unmistakable. The prints matched.

Sunita: Alright.

Arturo: America’s Robinhood had made his final escape.

Sunita: Into the afterlife!

Outro

Arturo: Yeahhhhh! That’s our story, Sunita.

Sunita: What an epic death. I mean, that is—that’s a better served ending. You know?

Arturo: Yeah, yeah. Like…

Sunita: It was feeling anti-climactic when he was just, like, caught. Even though like, yeah, he should be.

Arturo: Also, it feels like he’s getting caught because he like, keeps going to brothels and–

Sunita: I know. I know.

Arturo: I was like, I don’t know. He’s like, “this time around it’s gonna be fine.”

Sunita: Exactly.

Arturo: What are you taking away from the story? What was—what was something that really jumped out at you?

Sunita: Dude, truly, all the guns, like—just that there’s such a … everyone had like a stash of guns. Maybe not everyone, but like–

Arturo: No, every single person.

Sunita: Yeah, yeah.

Arturo: Everyone had a stash of Tommy guns.

Sunita: The amou—Tommy guns. That like … what the f***? That’s terrifying. I—I took away that like, the ’30s, this era, was terrifying.

Arturo: F***ing insane.

Sunita: I don’t wanna be there. I’m glad I’m not there.

Arturo: Let’s not go back there, but we’re gonna be there in like 10 years, just in a different type of ’30s. Hey, Sunita, thank you so much for being with us. Where can, uh, our listeners find you?

Sunita: Great question. Um, I guess I’m on the internet and, uh–

Arturo: Yeah, she’s on the, are you on the sosh meeds?

Sunita: I’m on the sosh meeds. I posted about things like upcoming movies and whatever on my Instagram.

Arturo: Wow. See? What are we, here? See, we’re gonna do a movie, see?

Sunita: I’m in the pictures.

Arturo: So find her @SunitaMani.

Sunita: That’s right.

Arturo: Uh. That’s your at?

Sunita: @SunitaMani. Yeah. My first last name. I—I got that one.

Arturo: Thank you so much, Sunita!

Sunita: Thanks for having me. Bye Arturo.

Arturo: Byeeeeee.

Credits

Arturo Castro: Greatest Escapes is a production of iHeartRadio and FilmNation Entertainment, in association with Gilded Audio. Our executive producers are me, Arturo Castro, Alyssa Martino and Milan Popelka from FilmNation Entertainment, Andrew Chugg and Whitney Donaldson from Gilded Audio, and Dylan Fagan from iHeartRadio.

The show is produced and edited by Carl Nellis and Ben Chugg, who are also, respectively, our research overlord and music overlord. Our associate producer is Tory Smith, who is our other overlord.

Nick Dooley is our technical director. Additional editing by Whitney Donaldson. Special thanks to Alison Cohen, Dan Welsh, Ben Ryzack, Sara Joyner, Nicki Stein, Olivia Canny, and Kelsey Albright.

Hey, thank you so much for listening, and if you’re enjoying the show, please leave a rating or review. My mom will call you each personally and thank you, and we’ll see you all next week.