WEBVTT

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Have you ever caught yourself watching one of

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those slick 1930s gangster movies? Oh, you mean

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the ones with the tailored pinstripe suits? Yeah,

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exactly. The suits and the fedoras tilted just

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right. Right, where the mastermind criminals

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are executing these flawless clockwork... bank

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heists. And they just look effortlessly cool

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and untouchable the whole time. I know exactly

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the vibe you're talking about. Well, today we

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are going to grab that polished Hollywood veneer

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and peel it right back. We really are. Because

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our mission for this deep dive is to look at

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the gritty and chaotic and frequently botched

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reality of a life of crime. Specifically during

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the infamous public enemy era. Right. And our

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source material for this journey is a highly

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detailed Wikipedia article chronicling the life

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and the incredibly bizarre death of John Hamilton.

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Also known as Red Hamilton. Yes, Red Hamilton,

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a Canadian born gangster from the 1920s and 30s.

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And a key heavy hitting associate of none other

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than John Dillinger. It's so great to have you

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here to dig into this. It is great to be diving

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into this with you. Where should we start? Well,

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to really set the mood for our analysis today,

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I want you to imagine the visual backdrop for

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our discussion. Okay, I'm picturing it. Picture

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a classic 1930s -style police evidence board

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right behind me. Oh, like the cork boards with

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the pushpins. Exactly. We're talking grainy black

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-and -white mugshots pinned to the board. Lots

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of newspaper clippings with those blaring sensational

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headlines. And a chaotic, sprawling web of red

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string. Connecting all the various bank heists

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and shootouts. And the hideouts screeching all

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across the American Midwest. That visual really

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puts you right in the shoes of the detectives

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trying to track this guy down. It does. Because

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I want you to imagine what it really takes to

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become a public enemy. It's not what the movies

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show. No, spoiler alert right out of the gate

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here. It is mostly just sheer panic. Terrible

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split -second decisions. And a whole lot of running

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in the dark. So true. So let's start at the very

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beginning. Who is the man behind the mugshot?

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Let's get into his origins. John Hamilton was

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born on August 27, 1898, up in Bing Inlet, Ontario.

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To an Irish -Canadian father and a German -American

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mother. Which is, uh... A rather unassuming origin

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point. It really is. When we analyze the great

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American gangsters of the 1930s, we don't typically

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picture a kid from a small logging community

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in Ontario. Right. You think of Chicago or New

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York. Exactly. But his story moves south of the

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border pretty quickly. And that's where the mythology

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really begins to take shape. The nicknames start

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flying. Oh, yeah. Before he even really... get

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started in his major criminal career, he picks

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up one of those classic, distinctly underworld

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nicknames. The papers called him Three Finger

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Jack. Now you might assume he got a name like

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that from some gritty underworld torture session.

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Or a bank vault door slamming on his hand during

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a getaway. Right, that sounds so cinematic. But

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nope. Nope. He lost two fingers on his right

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hand in a childhood sledding accident. A sledding

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accident. Just a normal winter kid thing gone

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wrong. It is a stark reminder of the era. long

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before modern safety standards or advanced reconstructive

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surgery. Yeah, definitely. But from an operational

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standpoint, that missing pair of fingers on his

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dominant hand would become his most defining

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physical characteristic. And as we'll see later,

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when we look at the pop culture surrounding him,

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it makes some of his Hollywood portrayals quite

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amusing. We will definitely get to the Hollywood

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treatment. But let's jump to the turning point

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in his life, the moment that really solidifies

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his path into the underworld. March. 1927. Right.

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Hamilton gets busted for robbing a gas station

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in Indiana. Just a single run -of -the -mill

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gas station. And for that crime, he is slapped

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with a staggering 25 -year prison sentence. 25

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years? Just wait a quarter of a century for a

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single gas station. I know. That seems wildly

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disproportionate, doesn't it? What's fascinating

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here is how that incredibly harsh, seemingly

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punitive sentence... completely backfired on

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the justice system. How so? Well, the intention,

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presumably, was to lock a petty thief away for

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good and protect society. Sure, keep him off

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the streets. But instead of rehabilitation or

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even just... basic deterrence. The Indiana State

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Prison effectively functioned as an elite networking

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event for the criminal underworld. Oh, wow. So

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they basically locked him in a concrete box with

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the worst people imaginable and hoped for the

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best. That is the tragic irony of the penal system

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at the time. Yeah. The state's attempt to isolate

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him actually gave him the exact infrastructure

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he needed to build a super gang. By throwing

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Hamilton into that specific environment in Michigan

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City for Two and a half decades. The state guaranteed

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he would rub shoulders with the most ambitious

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criminals of his generation. While incarcerated,

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Hamilton befriends absolute heavy hitters. We're

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talking about John Dillinger. Russell Clark.

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Charles Makely. Harry Pierpont. And Homer Van

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Meter. This wasn't just a group of inmates passing

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the time. Not at all. This was the incubation

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of a massive criminal enterprise. It's like the

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Avengers, but for robbing banks. That is a perfect

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way to put it. And they formed an incredibly

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tight bond in there. They really did. and Dillinger

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actually ends up getting paroled first in May

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of 1933. But he doesn't just walk away, get a

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legitimate job, and start a new life. No, he

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swears to liberate his friends. So Dillinger

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orchestrates this massive, highly coordinated

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smuggling operation from the outside. Getting

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handguns sneaked right into the prison. For Hamilton

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Makeley, Pierpont Clark, and the others. Which

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all culminates on September 26, 1933. With a

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massive 10 -man escape right out of the main

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gate of the Indiana State Prison. Walking out

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of the main gate of a state penitentiary is a

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brazen... operational success. It sounds impossible.

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It requires inside help, immense coordination,

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and sheer nerve. But the victory is incredibly

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short -lived. Because the landscape shifts almost

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immediately upon their exit. The newly freed

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gang quickly learns that their benefactor Dillinger

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had been busy on the outside. Very busy. He was

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arrested for bank robbery. And is now sitting

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in a cell in Lima, Ohio. So Dillinger broke them

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out. And now they have to return the favor. But

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jail breaks are not cheap. No, you need fast

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getaway cars, safe houses, bribes, and heavy

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weaponry. How do they pull together the capital

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for a rescue operation? They do what they do

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best. On October 3, 1933... Hamilton and the

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gang roll into St. Mary's, Ohio, and rob a bank.

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And they walk away with $14 ,000. Which is pushing

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$348 ,000 in 2025 money. A massive war chest.

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And with that immediate influx of cash, they

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execute the Lima jailbreak just nine days later.

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On October 12, 1933. Hamilton accompanies Charles

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Mackley, Harry Pierpont, Russell Clark, and Ed

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Shouse to free Dillinger. But there is a very

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crucial detail we need to point out here about

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the Lima jailbreak. Right. While Mackley and

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Pierpont burst into the building and end up murdering

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Sheriff Jess Sarber during the escape. Hamilton

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actually stayed outside. He didn't enter the

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jail and he did not participate in the shooting

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of the sheriff. That is a distinction that matters

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in a courtroom. But... Out on the street in the

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eyes of the law enforcement community. They were

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all painted with the exact same brush. The gang

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was now officially responsible for the death

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of a lawman. And that fundamental shift escalates

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the manhunt. They aren't just hunting bank robbers

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anymore. They are hunting cop killers. The rules

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of engagement completely change. And the escalation

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just keeps ramping up. By December 1933, the

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gang is feeling absolutely untouchable. They

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execute an armed invasion of a Chicago bank.

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Specifically targeting... The safe deposit boxes.

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They walk away with $50 ,000. Which today would

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be about $1 .24 million. They are flush with

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cash. Everything is going perfectly until...

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Until a massive mistake. Okay, let's unpack this.

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The absolute absurdity of how a multi -million

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dollar gang gets tripped up. It's almost hard

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to believe. Hamilton decides to leave his car

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at a Chicago garage to get some body work done.

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Considering the heat on them bringing a vehicle

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linked to an underworld syndicate into a public

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garage for cosmetic repairs. It is a staggering

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lapse in judgment. It really is. The mechanic

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at this garage takes one look at the vehicle,

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gets suspicious of what he literally calls this

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gangster car. And decides to call the cops. So

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Hamilton strolls back to the garage to pick up

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his ride, probably expecting to just pay his

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bill and drive off. And instead finds Detective

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William Shanley and two other officers waiting

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for him. Hamilton doesn't hesitate. He opens

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fire. He kills Detective Shanley right there

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at the garage and somehow manages to completely

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elude the other two officers and escape into

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the city. If we connect this to the bigger picture,

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this specific incident at the Chicago garage

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is a watershed moment in criminal history. Oh,

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so? We are seeing the death of the local reactive

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police force and the birth of the modern proactive

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dedicated task force. So Hamilton didn't just

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kill a cop. He inadvertently forced law enforcement

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to modernize. Exactly. This systemic reaction

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to the murder of Detective Shanley forces the

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Chicago Police Department to form a dedicated

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40 -man Dillinger squad. Solely focused on taking

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them down. 40 cops with one singular job. The

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walls are really starting to close in. And it

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leads to even more chaos. On January 15, 1934,

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Hamilton and Dillinger hit a bank in East Chicago,

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Indiana. Grabbing over $20 ,000. But it's an

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absolute bloodbath. Police officer William O'Malley

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is killed. Now, Dillinger is officially charged

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with O'Malley's murder. But multiple witnesses

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on the scene point the finger directly at Hamilton.

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Saying he was the actual shooter. And Hamilton

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doesn't walk away clean either. He takes two

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bullets during this heist. So the pressure on

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the syndicate is now immense. The sheer volume

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of law enforcement resources dedicated to finding

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them makes large group movements impossible.

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The gang realizes they are too hot to stay together,

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so they make the strategic decision to scatter.

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Dillinger and several others head down to Tucson,

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Arizona. Where they are subsequently apprehended.

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Right, they get caught. Meanwhile, a badly wounded

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Hamilton goes deep underground. He's left in

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the care of his girlfriend, Pat Charrington.

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and an underworld physician by the name of Joseph

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Moran. And with Dillinger behind bars in Arizona,

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Hamilton briefly rockets to the very top of the

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public enemies list. He is the number one most

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wanted man in America. But that ranking only

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lasts until Dillinger pulls off his legendary

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escape from Crown Point. Dillinger gets out,

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tracks down Hamilton, and they put together a

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brand new gang. And... Listen to this roster.

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You've got Hamilton Homer Van Meter, Tommy Carroll

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Eddie Green, and the notoriously unhinged Babyface

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Nelson. It is certainly a formidable lineup on

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paper. But the operational discipline of the

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original gang is completely gone. They embark

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on a string of robberies that are lucrative.

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but incredibly messy. The meticulous clockwork

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planning we associate with these heists is replaced

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by sheer violence, paranoia, and desperation.

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Here's where it gets really interesting because

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the universe just starts throwing absolutely

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wild curveballs at them. Just absolute chaos.

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Let's look at their hit in Sioux Falls. Babyface

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Nelson spots a motorcycle cop named Hale Keith

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and shoots him right through a plate glass window.

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Just senseless violence. And then they try to

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hit a bank in Mason City. And you will not believe

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this. What happened? Hamilton gets shot in the

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shoulder again, but not by the 40 -man Dillinger

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squad. Not by the FBI. He gets clipped by an

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elderly judge who happened to be looking out

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his window across the street and just decided

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to open fire on the gang. An elderly judge? From

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across the street. Dillinger is wounded in that

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same shootout, too. The visual of a highly armed

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supergang being pinned down by a senior citizen

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from across the street perfectly illustrates

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the total breakdown of their operational security.

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They aren't just fighting law enforcement anymore.

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The entire public is turning against them. They're

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bleeding, they are exhausted, and they have absolutely

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no safe harbor. So on April 17, 1934, Hamilton

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and Dillinger make a desperate, discreet visit

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to Hamilton's sister. Up in Salt St. Marie, Michigan.

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They're just trying to find a friendly face and

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catch their breath. After that, the gang retreats

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to a place called the Little Bohemia Resort deep

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in the woods of Wisconsin. They were looking

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for sanctuary and isolation, but they walked

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directly into a trap. On April 22nd, the resort

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is raided by the FBI. The operation is directed

00:12:23.289 --> 00:12:26.730
by the famous Melvin Purvis. The bureau had received

00:12:26.730 --> 00:12:29.370
a tip from a friend of the resort's owner. But

00:12:29.370 --> 00:12:32.470
the execution of this raid was a complete tragedy

00:12:32.470 --> 00:12:35.669
of errors. It was an absolute disaster. The FBI

00:12:35.669 --> 00:12:39.350
approached the resort in the freezing dark. Tensions

00:12:39.350 --> 00:12:42.710
were incredibly high. And in that tense, paranoid

00:12:42.710 --> 00:12:45.870
atmosphere, the agents mistakenly opened fire

00:12:45.870 --> 00:12:48.490
on a car pulling away from the lodge. But it

00:12:48.490 --> 00:12:50.769
wasn't the gangsters in the car. It was three

00:12:50.769 --> 00:12:54.529
local work camp employees. The FBI kills a man

00:12:54.529 --> 00:12:58.090
named Eugene Borno and severely wounds John Hoffman

00:12:58.090 --> 00:13:00.809
and John Morris. Just innocent guys leaving a

00:13:00.809 --> 00:13:03.710
lodge who got caught in the crossfire of this

00:13:03.710 --> 00:13:06.710
massive federal manhunt. And while the FBI is

00:13:06.710 --> 00:13:09.169
busy shooting at the wrong people, the actual

00:13:09.169 --> 00:13:12.009
gang inside realizes what's happening. And the

00:13:12.009 --> 00:13:13.929
escape they make is something out of a nightmare.

00:13:14.330 --> 00:13:16.309
Dillinger, Hamilton Van Meter, and Tommy Carroll

00:13:16.309 --> 00:13:18.210
have to leap from a second floor back window.

00:13:18.429 --> 00:13:20.870
Imagine the physical agony of that. They land

00:13:20.870 --> 00:13:23.230
on a mound of frozen snow in the dead of winter.

00:13:23.409 --> 00:13:25.409
Scrambling into the freezing darkness while nursing

00:13:25.409 --> 00:13:27.610
fresh bullet wounds. They run along the shore

00:13:27.610 --> 00:13:30.149
of Star Lake, desperate to get away. And finally

00:13:30.149 --> 00:13:32.450
manage to steal a car from a local carpenter

00:13:32.450 --> 00:13:34.509
about a half mile down the road. They survive

00:13:34.509 --> 00:13:37.029
the night, but the sheer physical toll of jumping

00:13:37.029 --> 00:13:39.309
from windows and running through the freezing

00:13:39.309 --> 00:13:42.090
Wisconsin woods was immense. And their luck had

00:13:42.090 --> 00:13:44.889
finally run out. Just one day later, on April

00:13:44.889 --> 00:13:48.250
23rd, another shootout occurs. In Hastings, Minnesota.

00:13:48.549 --> 00:13:51.629
Another town, another shootout. But this is the

00:13:51.629 --> 00:13:53.549
final one for Three Finger Jack. As they are

00:13:53.549 --> 00:13:56.789
fleeing in the escape car, Hamilton takes a mortal

00:13:56.789 --> 00:13:59.570
wound. He's dying in the backseat. So they drive

00:13:59.570 --> 00:14:01.990
him all the way back to Chicago, back to that

00:14:01.990 --> 00:14:04.549
underworld doctor, Joseph Moran. The same guy

00:14:04.549 --> 00:14:06.610
who patched him up just a few months prior. But

00:14:06.610 --> 00:14:09.419
this time... Moran takes one look at Hamilton

00:14:09.419 --> 00:14:13.080
and completely refuses to treat him. For reasons

00:14:13.080 --> 00:14:15.600
unknown, he just turns them away. He leaves him

00:14:15.600 --> 00:14:18.740
to die. So Dillinger is stuck with his dying

00:14:18.740 --> 00:14:21.600
friend in the backseat of a car. Dillinger, along

00:14:21.600 --> 00:14:24.220
with Volney Davis and Edna Murray, hide Hamilton

00:14:24.220 --> 00:14:26.840
in Aurora, Illinois. And there, over the course

00:14:26.840 --> 00:14:29.899
of a few agonizing days, John Hamilton dies on

00:14:29.899 --> 00:14:32.899
April 26. Dillinger and Davis take the body out

00:14:32.899 --> 00:14:35.659
near Oswego, Illinois, and bury their friend.

00:14:35.820 --> 00:14:37.559
And to make sure the cops can't identify him

00:14:37.559 --> 00:14:39.440
if he's found, they cover Hamilton's face and

00:14:39.440 --> 00:14:42.720
hands with lye. A brutal, undignified end to

00:14:42.720 --> 00:14:45.480
a brutal life. It really is. But the narrative

00:14:45.480 --> 00:14:47.580
doesn't actually end with his burial. So what

00:14:47.580 --> 00:14:49.519
does this all mean? It means the authorities

00:14:49.519 --> 00:14:51.500
were completely in the dark about his demise.

00:14:52.080 --> 00:14:54.299
The federal government is spending vast amounts

00:14:54.299 --> 00:14:57.740
of money and resources hunting a ghost. Almost

00:14:57.740 --> 00:15:00.139
three weeks after he was buried in that lie covered

00:15:00.139 --> 00:15:03.259
grave on May 19th, the government officially

00:15:03.259 --> 00:15:05.279
indicted him. And it gets even more bizarre.

00:15:05.440 --> 00:15:07.659
His sister, the one they visited up in Michigan,

00:15:07.840 --> 00:15:09.960
was actually convicted of harboring a fugitive.

00:15:10.100 --> 00:15:12.879
And spent time in prison all while her brother

00:15:12.879 --> 00:15:15.080
was already rotting in the ground. And because

00:15:15.080 --> 00:15:18.179
his death was kept secret by the gang. Rumors

00:15:18.179 --> 00:15:21.000
began to swirl that Hamilton had actually survived

00:15:21.000 --> 00:15:23.740
the Hastings shootout. It became an urban legend

00:15:23.740 --> 00:15:26.559
almost immediately. The FBI got countless tips

00:15:26.559 --> 00:15:29.279
from people claiming they saw him. Even Hamilton's

00:15:29.279 --> 00:15:31.740
own nephew stubbornly maintained that he had

00:15:31.740 --> 00:15:34.460
personally visited his uncle back in Ontario.

00:15:35.039 --> 00:15:37.700
Long after the supposed date of his death. But

00:15:37.700 --> 00:15:39.500
eventually the truth always comes out. Dental

00:15:39.500 --> 00:15:41.960
records proved the body in Oswego was indeed

00:15:41.960 --> 00:15:45.039
Three Finger Jack. They match the amalgam restorations,

00:15:45.080 --> 00:15:47.639
which are essentially his silver cavity fillings

00:15:47.639 --> 00:15:50.759
on the teeth of the corpse. With the dental records

00:15:50.759 --> 00:15:53.139
from his time at the Indiana State Penitentiary.

00:15:53.259 --> 00:15:56.320
Yet despite the grim, verified, and heavily documented

00:15:56.320 --> 00:15:59.220
reality of his life and death, popular culture

00:15:59.220 --> 00:16:02.440
couldn't resist reshaping his story. Oh, Hollywood

00:16:02.440 --> 00:16:04.519
absolutely loves playing Fast and Furious. loose

00:16:04.519 --> 00:16:06.440
with history. We talked about this at the beginning.

00:16:06.600 --> 00:16:09.659
Yes. Hamilton pops up in a bunch of media over

00:16:09.659 --> 00:16:12.580
the decades. He's featured in the 1957 movie

00:16:12.580 --> 00:16:15.600
Babyface Nelson. Stephen King even wrote a short

00:16:15.600 --> 00:16:18.000
story about his final days called The Death of

00:16:18.000 --> 00:16:20.450
Jack Hamilton. But my absolute favorite piece

00:16:20.450 --> 00:16:24.269
of pop culture inaccuracy is the 2009 film Public

00:16:24.269 --> 00:16:26.429
Enemies. What did they get wrong? Actor Jason

00:16:26.429 --> 00:16:28.789
Clarke plays Hamilton. He's up there on the big

00:16:28.789 --> 00:16:30.889
screen holding Tommy guns, driving the getaway

00:16:30.889 --> 00:16:32.850
cars. And let me guess, he has all his fingers.

00:16:33.049 --> 00:16:35.690
He very clearly has all five fingers on his right

00:16:35.690 --> 00:16:38.009
hand. They completely ignored the whole three

00:16:38.009 --> 00:16:40.669
-finger Jack moniker. They entirely ignored it.

00:16:40.730 --> 00:16:43.230
It is a perfect metaphor for how we sanitize

00:16:43.230 --> 00:16:45.509
history. We want the aesthetic of the roaring

00:16:45.509 --> 00:16:48.309
30s gangster without the gritty missing fingers.

00:16:48.299 --> 00:16:51.340
Exactly. And that is exactly why we do these

00:16:51.340 --> 00:16:53.899
deep dives for you. Because pop culture loves

00:16:53.899 --> 00:16:57.279
to romanticize these outlaws as smooth, calculated

00:16:57.279 --> 00:17:00.679
operators. But the reality was a brutal, chaotic

00:17:00.679 --> 00:17:04.599
series of botched raids. It was friendly fire.

00:17:04.839 --> 00:17:08.700
Getting shot by elderly judges. And dying a slow,

00:17:08.740 --> 00:17:11.500
secret death. Before we wrap up today, I know

00:17:11.500 --> 00:17:13.480
you had one more piece to add. I want to leave

00:17:13.480 --> 00:17:15.900
you with a final concept to mull over that wasn't

00:17:15.900 --> 00:17:18.730
previously discussed. You bet. Consider the collapse

00:17:18.730 --> 00:17:21.410
of the underworld ecosystem. What do you mean

00:17:21.410 --> 00:17:23.710
by that? When a criminal becomes so infamous,

00:17:23.950 --> 00:17:27.650
so highly targeted, that even the mob's own secret

00:17:27.650 --> 00:17:29.369
doctors - And the very people who profit off

00:17:29.369 --> 00:17:31.490
this violence - Refuse to treat them and leave

00:17:31.490 --> 00:17:34.369
them to die. What does that say about the absolute

00:17:34.369 --> 00:17:37.349
isolation of being a public enemy? Wow. At the

00:17:37.349 --> 00:17:40.390
very top of the criminal food chain, there is

00:17:40.390 --> 00:17:43.420
zero loyalty -only self -preservation. That is

00:17:43.420 --> 00:17:45.660
such a chilling point to end on, the absolute

00:17:45.660 --> 00:17:48.240
isolation of it all. It really reframes the whole

00:17:48.240 --> 00:17:50.599
gangster lifestyle. Thank you so much for joining

00:17:50.599 --> 00:17:53.119
us on this deep dive into the chaotic life of

00:17:53.119 --> 00:17:55.319
John Hamilton. It was a pleasure to unpack it

00:17:55.319 --> 00:17:56.980
all. We hope we've given you a new perspective

00:17:56.980 --> 00:17:59.579
on the reality behind the myth. Until next time,

00:17:59.599 --> 00:18:01.880
keep questioning the story and stay insanely

00:18:01.880 --> 00:18:02.339
curious.
