Original subtitles

In 1894, let him have it, the name Bill Doolin was on the lips of every lawman,

bounty hunter, and vigilante in the West.

I'd set Oklahoma territory ablaze with a crime spree that no criminal gang ever

matched before or since and won the biggest shootout in

outlaw history.

The shooting is just absolutely incredible.

The greatest fight between organized lawmen and outlaws ever in the West.

Do it!

Come on with your hands up! You can go to hell!

I rose to the top of a ruthless gang of desperadoes known far and wide as the

Dalton. Maybe I didn't hear you properly.

It sounds like you just called me a clown.

Until they became the Doolins.

Doolin's involved in more criminal acts than almost any gang in Western history.

My bold and brazen robberies made me the target of the biggest manhunt in

Oklahoma history.

Before I was through, I had blazed my name in criminal glory.

There's a real connection between Doolin and the James boys with those

Depression -era outlaws from the same region, Preboy Floyd, Bonnie and Clyde.

I lived a life of my own choosing, knowing full well what the outcome must

Hello, Bill. But sure as hell, I'd do it all over again.

By 1896, I, Bill Doolin, had spent many long years living on the wrong side of

the law.

I'd seen most of my comrades -in -arms gunned down in cold blood.

Yet I myself had managed to elude what the law called justice.

Oh, Bill!

But now...

Facing the rifles of a determined posse, I wondered whether the outlaw trail I'd

ridden so long had finally come.

When we remember Bill Doolin, we remember he's a killer and a thief, but

something about him that always made him a little more popular.

Bill Doolin actually was a natural leader. He was a likable guy.

Looked pretty good, you know. He was tall, rangy guy, 6 '2", 150 pounds.

He had winning ways.

You know, outlaws, just by the nature of their business, are romanticized.

You ask any outlaw, and he'll say it was injustice, desperation, or just rotten

luck that set him at odds with the law.

I've known plenty of criminally minded men, and to be sure, some of them were

just plain wicked.

But most, myself included, were decent folk to whom life had dealt an unfair

hand.

I started out in life with nothing but my family name and a willingness to

Bill Doolin was a son of sharecroppers.

Most sharecroppers' kids helped their parents.

So he probably worked hard when he was growing up.

He lived in Arkansas, and when he got old enough, he left home.

And he went to Indian Territory and wanted to be a cowboy.

By 1891, I was a ranch hand in Oklahoma, which was then called Indian

Territory. It was the last place in America where a man could still live

entirely free, beyond the reach of the law's ever -lengthening arm.

This was a place where people went to hide.

You could get lost there. But you have to remember how large an area this was.

It was 70 ,000 square miles.

Ranching was hard work that had paid a living wage, and I was glad to be

employed. But then I met the soon -to -be infamous Dalton brothers.

And from that moment on, my life would never be the same.

The Daltons certainly wanted to make a name for themselves.

In the 1890s, there's all these fantastic dime novels and the

newspaper, the Robin Hood, Frank and Jesse, Jamie Younger Brother.

This influenced them, I believe, to some extent.

All I'm saying, I don't see why selling alcohol to the Indians is illegal in the

first place.

I mean, you sure as hell get enough of it anyway.

Bob Dalton seems to have been the catalyst.

He was the one who gathered people together, and he was the cement for the

Dalton gang.

I bet you've heard the Dalton name painted in black as villainy.

But I knew them as decent folk, at least at first.

They served as lawmen for a time, but being too often cheated of their meager

pay, They turned to crime and dead.

As a matter of fact, I happen to know a fellow who's planning on bringing in a

load next month.

When Bob asked me to join them in their illicit trade, I hesitated at first,

figuring he was just blowing hot air.

Let's say we were serious about this now, Bill.

You reckon you want in on the share?

Maybe.

But seeing as you're not serious, this ain't nothing but bold talk, is it?

But the truth was, finding honest work was becoming almost impossible, and I

grown weary of leading a pauper's life.

Well, there were an awful lot of cowboys out of work in that period, and Doolam

was tired of being poor, and I can kind of understand his motivations, actually.

It wasn't long before Bob put his brazen plans into action.

and our humble band of ranchers became robbers. They started out with

introducing whiskey.

Then they went into horse thievery, stealing cattle.

And I think they found the excitement of it pleasurable.

The adrenaline rush of being chased and shot at became intoxicating for them.

Bill Doolin fell in with them, and he was kind of a natural leader, and he

take care of himself.

He was an excellent shot.

And so all of a sudden...

He's a key member of the Dalton gang.

That is a bet I will take, my friend.

Our first robberies were successful, and I enjoyed having money in my pocket for

a change.

The Dalton brothers were really more partners than friends.

They were rash and careless.

But Tulsa Jack Blake was like a brother.

I never knew a steadier man than he.

Nor a cooler hand in a gunfight.

Tulsa Jack Blake was a fast straw.

Very dangerous with a gun.

Unlike Tulsa Jack, Bitter Creek Newcomb was a carefree spirit.

And he was the very devil with the lady.

And Charlie Pierce was the finest horseman I ever met.

As well as a trusted friend.

Is that the job money? That is.

Now I took an extra share for myself since I pulled this all together.

If anyone minds, tell them to join some other outfit.

What you've got on each side here are two very strong men.

I have to wonder if Bill Doolin no longer wants to play this game the way

Dole plays it.

Maybe we ought to think about heading into Texas.

We're getting nowhere around here.

Well, don't you fret none, Bill.

I don't pay you to do my thinking for me.

Bill!

Don't go running off now.

Stay close by.

I've got something big shaping up.

Right out, boys.

Although I thought Bob had grown reckless, I kept my concerns to myself.

Until he told us of his plan for Coffeyville.

The robbery that would be the Dalton's last.

Simple as that.

We're in and out in 15 minutes. 20 tops.

The Coffeyville raid was Bob Dalton's idea.

And why did he want to do this? Well, of course he wanted the money.

But he also wanted to get a name for himself that was bigger than Jesse

Two banks.

In broad daylight.

At the same time.

Seems like a tall order, don't it?

Maybe. Maybe not.

Come on, boys.

We clean out these two banks, head on down to Mexico.

Well, hell, Jesse James never even pulled a caper like that.

So who's in?

You know, that's fine.

It's great, Bill.

We can do this without you.

It's, uh, you ain't got the fan for it.

Maybe I didn't hear you properly.

This sounds like you just called me a cunt.

Easy, fellas.

We're all friends here.

Enough talk.

Are you in or are you out?

No man alive can accuse me of lacking grit, but Bob's half -baked plan to rob

both of the banks in his own hometown, in broad daylight no less, was lunacy.

Good luck, fellas. You'll need it.

Come on, boys.

Tulsa Jack.

Bitter Creek, Charlie, and myself bid the Daltons adios.

And I reckon you know what happened next.

The Coffeyville debacle is the bloodiest street battle in the Old West.

A huge gunfight erupted between the would -be robbers and the townspeople

themselves.

After the smoke cleared, There were four dead outlaws.

The two brothers, Bob and Grant Dalton, had been killed.

And three citizens of Coffeyville had been killed.

I mean, they paid for this decision with their lives. I mean, they paid the

ultimate price for it.

I'd warned Bob against his foolish plan, but he hadn't listened to reason.

Now he and his brothers were dead.

For the rest of us boys, life went on.

Doolin put a gang together with the remnants of the Dalton gang. There's

books written about the Oklahoma Braves. It was usually referred to as the

Doolin gang because he was the face of the gang.

There you are. Thank you very much for your business.

The first robbery I led was nothing like the Dalton's death ride into

Coffinville. I made sure to strike where no one was looking.

and where no one knew my face.

Say, mister, is there someone here I could ask about alone?

Yes, sir, I'm your man.

300 long miles to the west of our old stomping grounds in Spearville, Kansas.

Let me just get straight to the withdrawal.

Hands up!

Get him up!

Come on.

Like I said, let's get straight to the withdrawal.

Look at me. Have you lost your mind?

Is that your money?

Give that to me.

Now bag it up.

Be quick.

I'd left Charlie Pierce watching the street, along with a new recruit we

Old Yanis.

Their job was to keep the locals under control.

Banks are closed.

And out of harm's way.

Time to go on home.

You. Y 'all get off the street. Get going. Time to go home.

Come on now. We knew the locals would take up arms against us once they

we were robbing their bank.

And guess what?

You're coming with us.

But I had a plan for that contingency as well.

The problem was that when they came out, by then the citizens were mobilizing.

They had armed themselves.

I ran the gauntlet beneath their rifles, trusting the vigilantes wouldn't risk

killing an innocent man.

I had no desire to shed the blood of townspeople who'd done me no wrong.

But I made it clear that if they wanted a bloody gunfight in Spearville, I'd

sure as hell give them one.

How the hell you doing?

Thanks for money.

I said put him down. You don't put him down, I'm going to blow this man's head

off.

Only a few weeks had passed since the Dalton gang had turned the rivers red in

Coffeyville.

Since then, I, Bill Doolin, had formed a gang

of my own.

And after a bold and bloodless robbery of the Spearville Bank, the Oklahoma

Braves were on the run.

Doolin was kind of like Butch Cassidy in that he would set up relays for horses

for getaways after he robbed banks and things like that. He was a smart outlaw.

I was confident we would escape our pursuers and that this was just the

beginning for the outlaw gang already known as the Oklahoma Braves.

Bill Doolin was a rebel. He liked action, liked what money could bring

needed that rush, the rush of fear, the rush of somebody shooting at you, and of

being on the lam.

With a swift horse beneath me and trusted friends at my side, I feared

death nor capture.

The Doolin gang's first robbery was a complete success, and there would be

to come.

Bill Doolin had a lot of leadership quality, and he made very good

which made him a very organized criminal and a very successful one.

As planned, we bled up after Spearville, confounding the lawmen on our trail.

But a few weeks later, I reconnected with the boys at our safe haven in the

outlaw -friendly town of Ingalls, Oklahoma.

He had all these guys with nicknames, Red Buck, Waitman, Dynamite, Dick

Arkansas Tom Jones, Little Bill Raylor, Little Dick West, and on and on with

these guys. The Oklahoma hombres.

Even as we bathed in our success, grim news arrived.

One of our own, Oleana, had been hunted down by so -called lawmen.

I didn't know it then, but it was important of things to come.

Typically, how law enforcement went after these guys is they would find out

where their friends and family were.

And so they tracked them down, and in the ensuing gunfight, Ole Yantis refuses

to give up, and even when he's shot down, he's reloading his gun several

The killing of old Yanis by a man purporting to enforce the law was a

pill to swallow.

Ladies, would you mind giving us a moment here? Thank you.

He'd had no trial, nor been convicted, but had been executed nonetheless.

Half the round.

Such was the state of justice in Oklahoma.

Now you listen, boys.

Those villains will serve us the same if they get a chance.

Well, I don't need to tell you that we're all riding a dangerous trail,

outside the law, and we're not keepers -robbers.

Now, each one of you here has got your own reason for turning out law, and it's

no business of mine.

So I'll understand if anyone wants to go the wrong way.

And do what, Bill?

Get a job?

Be it resolved, then, the Oklahoma Rays would ride again.

And the devil take the high most.

If

the

authorities in Oklahoma Territory thought we'd give up after they'd killed

of us, they thought wrong.

On June 10th, 1893, one of Doolin's gang members, Tulsa Jack Blake, flagged down

the California Express, part of the Santa Fe Railroad.

Railroad companies were my first choice to attack.

They were always carrying large amounts of cash.

Hey, get the hell down here, mister. This is a robbery.

And their unscrupulous practice made them the natural enemy of the working

I think trains were a good target because there was a resentment toward

railroads. They thought that they had taken all the best land, that they'd run

through people's property.

All right, boys.

Let's get to work.

Open up. They tried to get the messenger to open the door. I ain't going to

ask you twice.

Go to hell.

Have it your way, sir.

Let's go.

All right.

Let him have it.

They're firing shots, pistol shots, in through the door to get them to open,

there's no response.

It never fails to amaze me

when some sucker like you risk their life.

For railroad money. Well, it's my job, isn't it? At least it was.

I'd probably get fired for this.

Well, I do regret that, sir.

But at least you'll have a hell of a story to tell.

You'll be all right.

Anyone thinking of firing on us or giving chase, just remember that we

take a penny off anyone.

We got no quarrel with common folk.

But you give us cause, and we'll shoot you right down.

It was another flawless robbery.

No one had been killed, and we left the passengers in peace.

It was the railroad's money I wanted, not theirs.

That's the way successful train robbers did it, and that's the way Bill Doolin

usually did it.

You didn't want to kill anybody.

You didn't want to rough anybody out because that's going to turn the

against you.

We'd gotten away almost scot -free, save a lucky shot from a posse that

shattered my foot.

We scattered into the last true no -man's land of the frontier, the cowboy

of Oklahoma Territory.

It was a very friendly area towards them, especially in the town of Ingalls,

know, where they would spend a lot of their time.

Ingalls essentially made a deal with the devil. As long as the outlaws that came

to the town did not rob anyone or any of the businesses in town, they were

welcome to stay.

And the Ingalls people liked them. They came in and spent money. They were off

the beaten trail.

And it was also Bill Doolin's home territory.

Look sharp, Bill.

That's Heck Thomas.

I reckon he's here looking for you.

Heck Thomas was a terrific lawman.

He was in at least ten gunfights that I know of, and he was a fair man

and just as fine a western lawman as there ever was.

Better step out of the way, Doc.

Yeah, I don't see anything around here.

We should check out the center on the river bottom.

Up to now, no lawman had been able to bring the Oklahombrays to heel.

But E .D. Nix, the new U .S. Marshal, had orders to dismantle the outlaw class

in Oklahoma.

And he put his best men on the case.

Abbott, Dumas, Nix.

He had authority over 70 ,000 square miles criminal activity.

E .D. Nix had permission to stop the outlawry in Oklahoma at any cost, and he

didn't care if he had to kill these guys or not.

And sometimes killing them was an easier thing to do, too.

Mr. Nix was bound to determine he was going to take these outlaws out. He was

going to get them.

Harsha? I had mastered the outlaw's trade that killed the Dalton gang, but

faced a fearsome trio known as the Three Guardsmen.

Bill Tillman, Heck Thomas, and Chris Madsen were the

bravest lawmen west of the Mississippi.

Let's get right to the matter at hand, shall we? I have reason to suspect the

Doolin gang could be found right here in Ingalls.

And before the year's end, they would draw me into the bloodiest gunfight the

West would ever know.

Dolan! You're completely surrounded!

By 1893, I had become one of the most successful outlaws in Oklahoma

I had pulled off eight heights in just two years and raked in more than 30

in cash.

Bill Doolin put together a very efficient group of bandits and killers

a lot of robberies in Oklahoma.

September 1st, 1893.

dawned like any other day in Engle.

In the morning, the entire gang, with the exception of Arkansas Tom Jones, are

in the saloon.

They're drinking. They're playing cards. They're having a great time.

Arkansas Tom Jones is sick, and so he's upstairs in a hotel room.

We had no idea that by sunset, we'd blaze a new chapter in the bloody

the Old West.

Marcel E .D. Nix had sent a dozen of his best lawmen to Corrales, and among them

was at least one genuine Old West hero.

Jim Masterson was a famous lawman from Dog City, and the younger brother of Bat

Masterson.

He knew his business, and he at least knew what he was getting into.

You folks might want to go inside.

Jim Masterson, Bat's brother, rarely gets credit because of his brother,

He was an efficient lawman.

And Jim Masterson got involved in more gunfights than both of his older

put together.

Oh, I knew him. How are you supposed to be going down to Guthrie?

Oh, that's right.

Nixon's deputies came not to serve us warrants, but to shoot us down like

beasts.

And once again, it was a lawman who drew first blood.

All of a sudden, gunfire.

It's just the beginning.

Cover me, Jordan.

Bittercrete just galloped out of town as quick as he could. He was hit, and his

rifle was broken, and he couldn't help them.

Even the sick Arkansas Tom Jones is in the action.

He's shooting out at the posse from his upstairs window.

Most of the outlaws were covering Ransom Stallone.

There were later 172 bullet holes counted in the walls of Ransom Stallone.

Although none of the outlaws were hit.

Meanwhile in the town, five people have been gunned down.

One of them, a kid, was shot fatally.

Stallone! You're completely surrounded!

You better go.

The Doolans know that they're surrounded, where horses are in a livery

around the block.

And all of them, armed, come bursting out of the saloon.

Some of them go to the livery. They jump onto their horses.

By the time they leave town, they left in their wake at least six dead people,

including three deputy marshals and Arkansas Tom still in his hotel room.

That son of a bitch don't come down.

I'm going to blow that hotel to pieces with him in it.

Jim Matheson wanted to blow the entire hotel of smithereens with dynamite to

him out, which pretty much convinced Arkansas Tom that it was time to

He saw the game was up, and he knew that these guys, you know, were not going to

take many prisoners.

And when they told him that his pals had all galloped out of town and left

him there, he was, according to all reports, very deflated about it.

My God, Officer, I didn't want to hurt nobody, I swear.

If you want to make it to jail alive, I suggest you shut your mouth.

Get him!

So, Doolin has escaped.

This time, the bad guys won.

Mr. Nix was bound and determined he was going to take these outlaws out. He was

going to get them.

The Oklahoma Territory was so rife with banditry that he basically said, shoot

them all, ask the questions afterwards.

We'd escaped the murderous ambush sprung on us by E .D. Nix's guardsmen, but we

didn't emerge unscathed.

Bitter Creek Newcomb was badly wounded, and poor Tom was sentenced to 50 years

in prison.

Following the Ingalls raid, Doolin was basically running for his life at this

point, as were the other members of his gang.

When will you be back?

I don't know.

I'll send Mark.

Now the name Bill Doolin was on the lips of every lawman, vigilante, and bounty

hunter in Oklahoma.

And all of them are eager to cash in on my corpse.

All right, listen up.

I'm hiring up a posse this afternoon.

I need five men, horses, and rifles.

Each man will share the reward.

From that day forward, I was America's most wanted man.

Hello, Bill.

The law!

That duct up in Ingalls made me, Bill Doolin, the target of every lawman and

bounty hunter in the territory.

But the smoldering heat didn't deter the Oklahombrays.

We continued to ply our trade to perfection, pulling off one successful

after another.

For a time, I thought we'd lose the law forever.

But in truth, our days were numbered.

On April 3rd, 1895, Doolin and his Oklahombrays robbed the Rock Island

And things did not go well.

They didn't expect any real pursuit, but Chris Madsen was a pretty alert lawman,

and he put together a posse real quickly.

And when they rode up, it appears that Tulsa Jack Blake was on guard.

We got you now, you bastards.

Hocus off, you boys.

We're getting a little bit close behind them.

Paper might signal.

We'd already had close calls with E .D. Nick and the three guardsmen who'd

dogged our trail the length and breadth of Oklahoma.

This time, Chris Madsen got a step ahead of us.

And no doubt he thought he'd bring us back as either prisoners or corpses.

But Tulsi Jack Blake, God rest his soul, saved us from disaster.

One of the posse men brought him down with a bullet near the heart that killed

him instantly.

Jack's demise after so many faithful years at my side was a terrible blow.

But he died with his boots on, a free man until the very end.

And again, the Doolin gang escaped, as they had been doing for a long time and

would for not too much longer.

More and more of them were picked off. They didn't have a chance, which really

upset Doolin and made it worse for him.

After Tulsa Jack, Bitter Creek Newcomb and Charlie Pierce were the next to bite

the duct.

Murdered in their beds by bounty hunters.

Well, you know, it was 1896.

And at that point, he should have looked around. All the bad guys, all the guys

that had ridden with him, are getting killed by this time.

The West had become a hard place to be an outlaw in.

And he was kind of hoping to go somewhere else, maybe New Mexico.

But, you know, the bottom line is, what was he going to do there? It's hard to

imagine him living the life of an ordinary farmer.

With Oklahoma papered over by wanted posters bearing my name and suffering as

was from wounds received over years of outlaw life.

I decided to regain my health in Arkansas, far away, I presume, from the

presence of bounty hunters and lawmen. Bill Doolin had taken a severe wound in

the foot.

This had been a couple of years earlier, but what happened is it turned

rheumatic, and he had terrible pain.

He decided, while he's on the loose, to go to Eureka Springs to take the waters,

and maybe that would relieve his pain.

An informant told Bill Tillman about it. He goes to Eureka Springs. Almost

immediately, he encounters Doolin.

Bill Tillman, already well known as a very talented, successful buffalo

tracker, good man with a gun.

Bill is famous in Kansas, almost mythic in the state of Oklahoma.

Old Bill had spent years on my trail, hoping to bring the infamous Bill Doolin

to heel.

Now, it seemed, his moment had come at last.

Hello, Bill.

Deputy Tillman.

Looking well?

Don't make me blow the top of your head off.

Thinking of my family, I hesitated.

When in earlier years, I'd have sent Tillman to meet his maker.

You let me walk out of here without wearing handcuffs, I'll give you my word

I'll come quiet.

Get your hat, let's go.

Hillman caught me fair and square.

And unlike his murdering colleagues, he had the decency to let me surrender

peacefully.

I was faith and life in prison if convicted.

But I had no intention of ever standing trial at all.

Unlock this door, Danny, or I'll blow this man's head off.

After years of living on the run, the law had caught up with me at last.

Hello, Bill. I knew Bill Tillman, and he wasn't a man given to making empty

threats.

You let me walk out of here without wearing handcuffs, I'll give you my word

I'll come quiet.

But I also knew he was an honorable lawman who'd let me live if I

without violence.

Ladies.

The story is when Bill Tillman captures him, he's talked Doolin into pleading

guilty, and they won't hang him. They'll give him 50 years in prison.

As you've probably guessed by now, there was no way in hell I was going to wait

around for a trial.

Well, after Bill Doolin was arrested, he knew what it felt like to be locked up.

Considering all the crimes that he committed in his whole career, this is

only night he ever spent in jail.

which is kind of remarkable for someone with that resume.

I determined right away the guards were comically inept.

Breaking out would require only leadership and daring.

Naturally, I rose to the occasion.

They kind of figured out the guards.

One inmate would try a ruse that would, you know, make them open up the gate.

Hey, guard.

I'm going to drink a water.

Could you fill me up?

And so he tried to force this larger cup that he had that wouldn't fit through

the bar.

They got the keys,

opened up themselves.

And they got a gun from one of them.

Calm yourself.

It'll be over soon.

Unlock this door, damn you. I'll blow this man's head clean off.

Within minutes, I was out of jail and on the loose.

And I resolved never to step foot in a cell again.

I would live as a free man or die crying.

After Bill Doolin and several Confederates broke out of jail,

him. Tremendous manhunt.

He is hiding out at an old hideout of his, and he would come in every night

see his wife and kid.

They had people looking for him, and sure enough, they found him.

Again, I felt a strong premonition of danger.

But then at the time, I was accompanied by an acute sense of dread.

Somehow, I knew there could be no escape.

It was ultimately Heck Thomas who hunted Doolin down.

Bill!

And so Heck Thomas had the reputation of always giving a warning before he shot

somebody, and he gives Doolin a chance to give up.

I stood alone, helplessly surrounded by men who were eager to profit from my

death.

I had reached the end of the outlaw's path.

Well, Bill was not...

About to go gently into that good night. And Doolin goes for his Winchester.

Bullets and a shotgun blast are going to end Bill Doolin's criminal activities

forever.

Never again would I feel my wife's heartbeat against my own, nor the rush

galloping horse beneath me.

Death claims from all of us the joys we cherish most.

But I had died game, surrendering to no man, and went to my grave without

regret.

And of course, one of the most famous death portraits of the West is the

of Doolin Riddle by 21. Bullet holes in his...

Bill Doolin is shown shirtless, lying on his back, head turned to the side, eyes

still open.

Many bullet holes on him, and each one looked like about the size of a quarter.

And so his career of outlawry ended violently, as did that of most of

the guys that ran with him.

I think that Bill Doolin deserves more recognition than he's gotten over the

years. He was a wily outlaw, and he wasn't bloodthirsty either.

We got no quarrel with common folk.

Maybe I didn't hear you properly.

This sounds like you just called me a cunt.

It's kind of ironic that Doolin, of all the outlaws, probably did more to bring

peace to the Oklahoma Territory than anybody else.

because of all the heat that he drew from law enforcement.

Doolin, he makes it impossible for lawmen who actually sort of like to, to

let him go.

How's Edith?

Oh, she will not be pleased with me. They have to bring him in, and they have

bring him in with his boots on.

Bill! Paul!