Have you ever caught yourself watching one of
those slick 1930s gangster movies? Oh, you mean
the ones with the tailored pinstripe suits? Yeah,
exactly. The suits and the fedoras tilted just
right. Right, where the mastermind criminals
are executing these flawless clockwork... bank
heists. And they just look effortlessly cool
and untouchable the whole time. I know exactly
the vibe you're talking about. Well, today we
are going to grab that polished Hollywood veneer
and peel it right back. We really are. Because
our mission for this deep dive is to look at
the gritty and chaotic and frequently botched
reality of a life of crime. Specifically during
the infamous public enemy era. Right. And our
source material for this journey is a highly
detailed Wikipedia article chronicling the life
and the incredibly bizarre death of John Hamilton.
Also known as Red Hamilton. Yes, Red Hamilton,
a Canadian born gangster from the 1920s and 30s.
And a key heavy hitting associate of none other
than John Dillinger. It's so great to have you
here to dig into this. It is great to be diving
into this with you. Where should we start? Well,
to really set the mood for our analysis today,
I want you to imagine the visual backdrop for
our discussion. Okay, I'm picturing it. Picture
a classic 1930s -style police evidence board
right behind me. Oh, like the cork boards with
the pushpins. Exactly. We're talking grainy black
-and -white mugshots pinned to the board. Lots
of newspaper clippings with those blaring sensational
headlines. And a chaotic, sprawling web of red
string. Connecting all the various bank heists
and shootouts. And the hideouts screeching all
across the American Midwest. That visual really
puts you right in the shoes of the detectives
trying to track this guy down. It does. Because
I want you to imagine what it really takes to
become a public enemy. It's not what the movies
show. No, spoiler alert right out of the gate
here. It is mostly just sheer panic. Terrible
split -second decisions. And a whole lot of running
in the dark. So true. So let's start at the very
beginning. Who is the man behind the mugshot?
Let's get into his origins. John Hamilton was
born on August 27, 1898, up in Bing Inlet, Ontario.
To an Irish -Canadian father and a German -American
mother. Which is, uh... A rather unassuming origin
point. It really is. When we analyze the great
American gangsters of the 1930s, we don't typically
picture a kid from a small logging community
in Ontario. Right. You think of Chicago or New
York. Exactly. But his story moves south of the
border pretty quickly. And that's where the mythology
really begins to take shape. The nicknames start
flying. Oh, yeah. Before he even really... get
started in his major criminal career, he picks
up one of those classic, distinctly underworld
nicknames. The papers called him Three Finger
Jack. Now you might assume he got a name like
that from some gritty underworld torture session.
Or a bank vault door slamming on his hand during
a getaway. Right, that sounds so cinematic. But
nope. Nope. He lost two fingers on his right
hand in a childhood sledding accident. A sledding
accident. Just a normal winter kid thing gone
wrong. It is a stark reminder of the era. long
before modern safety standards or advanced reconstructive
surgery. Yeah, definitely. But from an operational
standpoint, that missing pair of fingers on his
dominant hand would become his most defining
physical characteristic. And as we'll see later,
when we look at the pop culture surrounding him,
it makes some of his Hollywood portrayals quite
amusing. We will definitely get to the Hollywood
treatment. But let's jump to the turning point
in his life, the moment that really solidifies
his path into the underworld. March. 1927. Right.
Hamilton gets busted for robbing a gas station
in Indiana. Just a single run -of -the -mill
gas station. And for that crime, he is slapped
with a staggering 25 -year prison sentence. 25
years? Just wait a quarter of a century for a
single gas station. I know. That seems wildly
disproportionate, doesn't it? What's fascinating
here is how that incredibly harsh, seemingly
punitive sentence... completely backfired on
the justice system. How so? Well, the intention,
presumably, was to lock a petty thief away for
good and protect society. Sure, keep him off
the streets. But instead of rehabilitation or
even just... basic deterrence. The Indiana State
Prison effectively functioned as an elite networking
event for the criminal underworld. Oh, wow. So
they basically locked him in a concrete box with
the worst people imaginable and hoped for the
best. That is the tragic irony of the penal system
at the time. Yeah. The state's attempt to isolate
him actually gave him the exact infrastructure
he needed to build a super gang. By throwing
Hamilton into that specific environment in Michigan
City for Two and a half decades. The state guaranteed
he would rub shoulders with the most ambitious
criminals of his generation. While incarcerated,
Hamilton befriends absolute heavy hitters. We're
talking about John Dillinger. Russell Clark.
Charles Makely. Harry Pierpont. And Homer Van
Meter. This wasn't just a group of inmates passing
the time. Not at all. This was the incubation
of a massive criminal enterprise. It's like the
Avengers, but for robbing banks. That is a perfect
way to put it. And they formed an incredibly
tight bond in there. They really did. and Dillinger
actually ends up getting paroled first in May
of 1933. But he doesn't just walk away, get a
legitimate job, and start a new life. No, he
swears to liberate his friends. So Dillinger
orchestrates this massive, highly coordinated
smuggling operation from the outside. Getting
handguns sneaked right into the prison. For Hamilton
Makeley, Pierpont Clark, and the others. Which
all culminates on September 26, 1933. With a
massive 10 -man escape right out of the main
gate of the Indiana State Prison. Walking out
of the main gate of a state penitentiary is a
brazen... operational success. It sounds impossible.
It requires inside help, immense coordination,
and sheer nerve. But the victory is incredibly
short -lived. Because the landscape shifts almost
immediately upon their exit. The newly freed
gang quickly learns that their benefactor Dillinger
had been busy on the outside. Very busy. He was
arrested for bank robbery. And is now sitting
in a cell in Lima, Ohio. So Dillinger broke them
out. And now they have to return the favor. But
jail breaks are not cheap. No, you need fast
getaway cars, safe houses, bribes, and heavy
weaponry. How do they pull together the capital
for a rescue operation? They do what they do
best. On October 3, 1933... Hamilton and the
gang roll into St. Mary's, Ohio, and rob a bank.
And they walk away with $14 ,000. Which is pushing
$348 ,000 in 2025 money. A massive war chest.
And with that immediate influx of cash, they
execute the Lima jailbreak just nine days later.
On October 12, 1933. Hamilton accompanies Charles
Mackley, Harry Pierpont, Russell Clark, and Ed
Shouse to free Dillinger. But there is a very
crucial detail we need to point out here about
the Lima jailbreak. Right. While Mackley and
Pierpont burst into the building and end up murdering
Sheriff Jess Sarber during the escape. Hamilton
actually stayed outside. He didn't enter the
jail and he did not participate in the shooting
of the sheriff. That is a distinction that matters
in a courtroom. But... Out on the street in the
eyes of the law enforcement community. They were
all painted with the exact same brush. The gang
was now officially responsible for the death
of a lawman. And that fundamental shift escalates
the manhunt. They aren't just hunting bank robbers
anymore. They are hunting cop killers. The rules
of engagement completely change. And the escalation
just keeps ramping up. By December 1933, the
gang is feeling absolutely untouchable. They
execute an armed invasion of a Chicago bank.
Specifically targeting... The safe deposit boxes.
They walk away with $50 ,000. Which today would
be about $1 .24 million. They are flush with
cash. Everything is going perfectly until...
Until a massive mistake. Okay, let's unpack this.
The absolute absurdity of how a multi -million
dollar gang gets tripped up. It's almost hard
to believe. Hamilton decides to leave his car
at a Chicago garage to get some body work done.
Considering the heat on them bringing a vehicle
linked to an underworld syndicate into a public
garage for cosmetic repairs. It is a staggering
lapse in judgment. It really is. The mechanic
at this garage takes one look at the vehicle,
gets suspicious of what he literally calls this
gangster car. And decides to call the cops. So
Hamilton strolls back to the garage to pick up
his ride, probably expecting to just pay his
bill and drive off. And instead finds Detective
William Shanley and two other officers waiting
for him. Hamilton doesn't hesitate. He opens
fire. He kills Detective Shanley right there
at the garage and somehow manages to completely
elude the other two officers and escape into
the city. If we connect this to the bigger picture,
this specific incident at the Chicago garage
is a watershed moment in criminal history. Oh,
so? We are seeing the death of the local reactive
police force and the birth of the modern proactive
dedicated task force. So Hamilton didn't just
kill a cop. He inadvertently forced law enforcement
to modernize. Exactly. This systemic reaction
to the murder of Detective Shanley forces the
Chicago Police Department to form a dedicated
40 -man Dillinger squad. Solely focused on taking
them down. 40 cops with one singular job. The
walls are really starting to close in. And it
leads to even more chaos. On January 15, 1934,
Hamilton and Dillinger hit a bank in East Chicago,
Indiana. Grabbing over $20 ,000. But it's an
absolute bloodbath. Police officer William O'Malley
is killed. Now, Dillinger is officially charged
with O'Malley's murder. But multiple witnesses
on the scene point the finger directly at Hamilton.
Saying he was the actual shooter. And Hamilton
doesn't walk away clean either. He takes two
bullets during this heist. So the pressure on
the syndicate is now immense. The sheer volume
of law enforcement resources dedicated to finding
them makes large group movements impossible.
The gang realizes they are too hot to stay together,
so they make the strategic decision to scatter.
Dillinger and several others head down to Tucson,
Arizona. Where they are subsequently apprehended.
Right, they get caught. Meanwhile, a badly wounded
Hamilton goes deep underground. He's left in
the care of his girlfriend, Pat Charrington.
and an underworld physician by the name of Joseph
Moran. And with Dillinger behind bars in Arizona,
Hamilton briefly rockets to the very top of the
public enemies list. He is the number one most
wanted man in America. But that ranking only
lasts until Dillinger pulls off his legendary
escape from Crown Point. Dillinger gets out,
tracks down Hamilton, and they put together a
brand new gang. And... Listen to this roster.
You've got Hamilton Homer Van Meter, Tommy Carroll
Eddie Green, and the notoriously unhinged Babyface
Nelson. It is certainly a formidable lineup on
paper. But the operational discipline of the
original gang is completely gone. They embark
on a string of robberies that are lucrative.
but incredibly messy. The meticulous clockwork
planning we associate with these heists is replaced
by sheer violence, paranoia, and desperation.
Here's where it gets really interesting because
the universe just starts throwing absolutely
wild curveballs at them. Just absolute chaos.
Let's look at their hit in Sioux Falls. Babyface
Nelson spots a motorcycle cop named Hale Keith
and shoots him right through a plate glass window.
Just senseless violence. And then they try to
hit a bank in Mason City. And you will not believe
this. What happened? Hamilton gets shot in the
shoulder again, but not by the 40 -man Dillinger
squad. Not by the FBI. He gets clipped by an
elderly judge who happened to be looking out
his window across the street and just decided
to open fire on the gang. An elderly judge? From
across the street. Dillinger is wounded in that
same shootout, too. The visual of a highly armed
supergang being pinned down by a senior citizen
from across the street perfectly illustrates
the total breakdown of their operational security.
They aren't just fighting law enforcement anymore.
The entire public is turning against them. They're
bleeding, they are exhausted, and they have absolutely
no safe harbor. So on April 17, 1934, Hamilton
and Dillinger make a desperate, discreet visit
to Hamilton's sister. Up in Salt St. Marie, Michigan.
They're just trying to find a friendly face and
catch their breath. After that, the gang retreats
to a place called the Little Bohemia Resort deep
in the woods of Wisconsin. They were looking
for sanctuary and isolation, but they walked
directly into a trap. On April 22nd, the resort
is raided by the FBI. The operation is directed
by the famous Melvin Purvis. The bureau had received
a tip from a friend of the resort's owner. But
the execution of this raid was a complete tragedy
of errors. It was an absolute disaster. The FBI
approached the resort in the freezing dark. Tensions
were incredibly high. And in that tense, paranoid
atmosphere, the agents mistakenly opened fire
on a car pulling away from the lodge. But it
wasn't the gangsters in the car. It was three
local work camp employees. The FBI kills a man
named Eugene Borno and severely wounds John Hoffman
and John Morris. Just innocent guys leaving a
lodge who got caught in the crossfire of this
massive federal manhunt. And while the FBI is
busy shooting at the wrong people, the actual
gang inside realizes what's happening. And the
escape they make is something out of a nightmare.
Dillinger, Hamilton Van Meter, and Tommy Carroll
have to leap from a second floor back window.
Imagine the physical agony of that. They land
on a mound of frozen snow in the dead of winter.
Scrambling into the freezing darkness while nursing
fresh bullet wounds. They run along the shore
of Star Lake, desperate to get away. And finally
manage to steal a car from a local carpenter
about a half mile down the road. They survive
the night, but the sheer physical toll of jumping
from windows and running through the freezing
Wisconsin woods was immense. And their luck had
finally run out. Just one day later, on April
23rd, another shootout occurs. In Hastings, Minnesota.
Another town, another shootout. But this is the
final one for Three Finger Jack. As they are
fleeing in the escape car, Hamilton takes a mortal
wound. He's dying in the backseat. So they drive
him all the way back to Chicago, back to that
underworld doctor, Joseph Moran. The same guy
who patched him up just a few months prior. But
this time... Moran takes one look at Hamilton
and completely refuses to treat him. For reasons
unknown, he just turns them away. He leaves him
to die. So Dillinger is stuck with his dying
friend in the backseat of a car. Dillinger, along
with Volney Davis and Edna Murray, hide Hamilton
in Aurora, Illinois. And there, over the course
of a few agonizing days, John Hamilton dies on
April 26. Dillinger and Davis take the body out
near Oswego, Illinois, and bury their friend.
And to make sure the cops can't identify him
if he's found, they cover Hamilton's face and
hands with lye. A brutal, undignified end to
a brutal life. It really is. But the narrative
doesn't actually end with his burial. So what
does this all mean? It means the authorities
were completely in the dark about his demise.
The federal government is spending vast amounts
of money and resources hunting a ghost. Almost
three weeks after he was buried in that lie covered
grave on May 19th, the government officially
indicted him. And it gets even more bizarre.
His sister, the one they visited up in Michigan,
was actually convicted of harboring a fugitive.
And spent time in prison all while her brother
was already rotting in the ground. And because
his death was kept secret by the gang. Rumors
began to swirl that Hamilton had actually survived
the Hastings shootout. It became an urban legend
almost immediately. The FBI got countless tips
from people claiming they saw him. Even Hamilton's
own nephew stubbornly maintained that he had
personally visited his uncle back in Ontario.
Long after the supposed date of his death. But
eventually the truth always comes out. Dental
records proved the body in Oswego was indeed
Three Finger Jack. They match the amalgam restorations,
which are essentially his silver cavity fillings
on the teeth of the corpse. With the dental records
from his time at the Indiana State Penitentiary.
Yet despite the grim, verified, and heavily documented
reality of his life and death, popular culture
couldn't resist reshaping his story. Oh, Hollywood
absolutely loves playing Fast and Furious. loose
with history. We talked about this at the beginning.
Yes. Hamilton pops up in a bunch of media over
the decades. He's featured in the 1957 movie
Babyface Nelson. Stephen King even wrote a short
story about his final days called The Death of
Jack Hamilton. But my absolute favorite piece
of pop culture inaccuracy is the 2009 film Public
Enemies. What did they get wrong? Actor Jason
Clarke plays Hamilton. He's up there on the big
screen holding Tommy guns, driving the getaway
cars. And let me guess, he has all his fingers.
He very clearly has all five fingers on his right
hand. They completely ignored the whole three
-finger Jack moniker. They entirely ignored it.
It is a perfect metaphor for how we sanitize
history. We want the aesthetic of the roaring
30s gangster without the gritty missing fingers.
Exactly. And that is exactly why we do these
deep dives for you. Because pop culture loves
to romanticize these outlaws as smooth, calculated
operators. But the reality was a brutal, chaotic
series of botched raids. It was friendly fire.
Getting shot by elderly judges. And dying a slow,
secret death. Before we wrap up today, I know
you had one more piece to add. I want to leave
you with a final concept to mull over that wasn't
previously discussed. You bet. Consider the collapse
of the underworld ecosystem. What do you mean
by that? When a criminal becomes so infamous,
so highly targeted, that even the mob's own secret
doctors - And the very people who profit off
this violence - Refuse to treat them and leave
them to die. What does that say about the absolute
isolation of being a public enemy? Wow. At the
very top of the criminal food chain, there is
zero loyalty -only self -preservation. That is
such a chilling point to end on, the absolute
isolation of it all. It really reframes the whole
gangster lifestyle. Thank you so much for joining
us on this deep dive into the chaotic life of
John Hamilton. It was a pleasure to unpack it
all. We hope we've given you a new perspective
on the reality behind the myth. Until next time,
keep questioning the story and stay insanely
curious.