Legends of the Old West - THREE GUARDSMEN Ep. 6 | Bill Tilghman: “The End of the Outlaws”
Episode Date: August 24, 2022As the battle raged between the U.S. Marshals and the Doolin-Dalton Gang, Tilghman narrowly missed a legendary – but tragic – shootout between the two sides. In the aftermath, an elite group of ma...nhunters, including Tilghman, pursued the gang day and night. Tilghman had the honor of cornering Bill Doolin, but he would need Heck Thomas’s help to finally put an end to the “king of the outlaws.” Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join To advertise on this podcast, please email: sales@advertisecast.com For more details, visit our website www.blackbarrelmedia.com and check out our social media pages. We’re @OldWestPodcast on Facebook, Instagram and Twitter. This show is part of the Airwave Media podcast network. Please visit AirwaveMedia.com to check out other great podcasts like Ben Franklin’s World, Once Upon A Crime, and many more. Learn more about your ad choices. Visit megaphone.fm/adchoices
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In April of 1889, 34-year-old Bill Tillman was allowed to enter Oklahoma just before its first land rush and grab a spot.
Nearly two million acres of land opened up to White's
settlement in Indian Territory. Months earlier, Tillman had been a lawman in Dodge. There he took
a bullet in the thigh during a quasi-legal removal of election records in an event called the Gray
County War. Tillman recovered from his wound, but lost his home. By 1889, he was forced to walk away from
it like so many others. The Kansas boom went bust, and he couldn't make the tax burden.
Because Tillman had such a stellar reputation as a lawman in Dodge, the mayor of the brand-new town
of Guthrie, Oklahoma, hired him and Jim Masterson, younger brother of Bat and Ed, to rid the city
of squatters. After a federal court was established at Guthrie in 1889, Tillman was appointed a deputy
U.S. marshal. Though Tillman never touched a drop of alcohol, one of the first things he did when
he arrived in Guthrie was to open a saloon. That was perfectly legal and a welcome
business in the new territory of Oklahoma. But what wasn't legal was gambling, at least not
within the confines of a saloon. But Tillman's name and that of his brother Frank showed up at
least 19 times in the Guthrie arrest records over the next two years for maintaining a house of gambling. He always bonded
out, and somehow the arrests never made it into the newspapers. His last recorded arrest was in
August of 1892, by which time he had paid over $450 in fines. Tillman also established a horse
track in Guthrie. Again, that was legal, but some of the
entertainment he offered to visiting thoroughbred owners was not. That included access to gambling
and prostitution at his saloon. Still, residents were happy to look the other way because Tillman
kept the peace, and that kept his name out of the papers. In 1893, in another land rush,
his name out of the papers. In 1893, in another land rush, Tillman acquired an even bigger piece of land and built a ranch. His claim was in a part of the Cherokee Strip, whose county seat
was the city of Perry. Within a month, Tillman was elected Marshal of Perry. Close to the time
of Tillman's new land purchase, 14 Deputy U.S. Marshals entered Ingalls, Oklahoma,
a haven for the notorious Doolin Dalton gang.
In a brazen and bloody gunfight, three of the deputies were killed, while most of the gang escaped without a scratch.
And for the next five years, much of Deputy U.S. Marshal Bill Tillman's life would revolve around avenging his fallen friends.
He and the rest of the Marshal Service vowed to bring down the Doolin-Dalton gang no matter what it cost.
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From Black Barrel Media, this is Legends of the Old West. I'm your host, Chris Wimmer, and this season we're telling the stories of the Three Guardsmen,
the trio of U.S. Marshals who neutralized some of the worst criminals in the Old West.
This is Episode 6, Bill Tillman, The End of the Outlaws.
In May of 1891, while Bill Tillman was getting himself established in Oklahoma Territory,
five masked men stopped a Santa Fe train and stole $1,500. They would have gotten more,
but the express messenger cleverly hid the bulk of his cargo in the train's stove. It was the same
trick Heck Thomas pulled 13 years earlier
when he was an express messenger and confronted by the Sam Bass gang. After the robbery, 200 men
searched for members of the Dalton gang. The accumulated reward stood at $6,000. No one caught
the elusive criminals, so they were free to strike again in September of 1891.
They robbed the Missouri, Kansas, and Texas Railroad of $25,000.
They did it so quietly that the passengers didn't even realize the train was being robbed.
Then, the Santa Fe train was robbed at Red Rock in June of 1892, supposedly by some of the same gang.
at Red Rock in June of 1892, supposedly by some of the same gang. They made off with at least $50,000 and maybe as much as $70,000. That was three high-profile train robberies in Oklahoma
territory in the space of a year. It couldn't be proved that members of the Dalton gang committed
all the robberies, but they were the top targets, and they knew it.
robberies, but they were the top targets, and they knew it. U.S. Marshal William Grimes,
Deputy Chris Madsen, and a deputy named Tillman Lilly captured a few of the bandits who robbed the train at Red Rock. But the arrests didn't cause the gang to so much as pause. In July of 1892,
the Dalton gang held up a train at Adair, where one man was killed
and four were wounded. Although eight guards were on board the train, the gang blew open the safe
and made off with an unknown sum of money. The robbery might have been lucrative, but it added
more heat on their trail. Deputy Marshal Heck Thomas, among others,
was now chasing them.
Ultimately, it spurred them to make one last big score
before they fled the area.
The Corps members of the gang robbed two banks
in Coffeyville, Kansas in October 1892,
three months after the Adair train robbery.
Four of the five robbers died in the infamous raid,
and only Emmett Dalton lived to tell the tale. After that disaster, Bill Doolin organized his
own gang of assorted misfits and criminals. A few weeks after Coffeyville, he, along with
outlaws George Newcomb and Oliver Yantis, robbed a bank west of Dodge City. Some deputies, including Chris
Madsen, chased them through western Oklahoma. They found Yantis at his sister's house and killed him
during a shootout. A few months later, Madsen learned that Doolin, Bill Dalton, George Newcomb,
and Bill Blake robbed a train at Cimarron, Kansas. Madsen's posse found the outlaw's trail,
and Madsen fired a shot that wounded Doolin in the foot, but the robbers managed to escape anyway.
Bill Tillman had only been a deputy marshal in Guthrie, Oklahoma, for 18 months when Madsen
killed Oliver Yantis, and the hunt for Bill Doolin intensified. In July of 1893, the new U.S.
Marshal for Oklahoma, E.D. Nix, received special funds from the government to hunt the Doolin
Dalton gang. Ideally, Nix wanted the gang to appear in the courtroom of Judge Isaac Parker
in Fort Smith, Arkansas. Parker had earned the nickname
the Hanging Judge because of his propensity for sending criminals to the gallows.
But neither Nix nor Parker nor the people of Oklahoma were going to lose sleep if the outlaws
ended up dead. To that end, Nix learned that some of the gang members were resting in a dusty hamlet
called Ingalls, which was a few miles east of the small city were resting in a dusty hamlet called Ingalls,
which was a few miles east of the small city of Stillwater, which is the home of Oklahoma State University.
On August 31, 1893, Marshall Nix mustered a 13-man posse of Oklahoma's best lawmen.
The team included Jim Masterson, younger brother of Bat Masterson, and would have included Bill Tillman, but Tillman was laid up from an accident and couldn't go along.
He missed one of the deadliest shootouts between lawmen and outlaws in the Old West, and it might have saved his life.
On the night of August 31st, the posse camped outside town.
Reconnaissance told them that virtually the entire gang was hanging out at a particular saloon
after a summer's worth of train robberies.
Bill Doolin was there, of course, and so were his compatriots with colorful nicknames.
There was Dan Clifton, known as Dynamite Dick, George Waitman, known as
Red Buck, George Newcomb, known as Bitter Creek, Roy Doherty, known as Arkansas Tom, and Bill Blake,
known as Tulsa Jack. One of the deputy marshals was leery of going into town to try to arrest the
gang, even when the lawmen outnumbered the gang
members almost two to one. The gang had proven repeatedly that it had no trouble killing civilians
or lawmen to avoid capture. The deputy sent a rider to nearby Stillwater to gather reinforcements.
It's not clear why the posse didn't wait for the reinforcements. Maybe they thought they'd
lose their chance to strike, but they headed toward Ingalls and a saloon full of outlaws.
It was nighttime in Oklahoma Territory. The posse split into two groups, and most of the men laid
down in the backs of two covered wagons. Jim Masterson drove one of the wagons toward town from the west. Deputy Richard
Speed drove the other wagon toward town from the east. When the wagons reached the outskirts of
town, the deputies hopped out and walked the rest of the way. They took cover outside the saloon
and waited to make their move, but there was no real chance to coordinate a plan.
to make their move, but there was no real chance to coordinate a plan. A couple moments after Deputy Speed stepped down from his wagon, he saw a man who looked like George Bitter Creek Newcomb
walk out of the saloon. It was Newcomb, and he was leaving the party early to go see his girlfriend.
Speed grabbed a 14-year-old boy standing near him and hissed at him to identify the man.
grabbed a 14-year-old boy standing near him and hissed at him to identify the man.
The boy, of course, had no idea what was going on,
so he pointed straight at the outlaw and said Newcomb's name out loud.
When Newcomb heard his name, he wheeled around with his Winchester ready to fire.
Deputy Speed was faster. He fired, and the bullet should have gutted Newcomb,
but instead, it crashed straight into the center of Newcomb's gun barrel.
The Winchester basically exploded and showered Newcomb with shards of wood and steel.
But Newcomb was still able to run, and he dashed for cover nearby.
Meanwhile, Roy Doherty heard the commotion from a second-story hotel window.
He waited like a sniper.
When Deputy Speed broke cover to chase Newcomb,
Doherty fired from the hotel window, and Newcomb fired from street level.
If either outlaw hit Speed at that moment,
Speed didn't go down, though he wouldn't be in the fight much longer.
The first round of shots happened so fast,
the deputies felt they had no choice but to take
extreme action. The scene that followed would be reenacted in countless Hollywood movies in the
years to come. The lawmen had lost the element of surprise, so they opened fire on the saloon
from the outside. Wood splintered and glass shattered, and inside the saloon, the outlaws returned fire.
Somewhere around 20 men were blasting away at each other in the middle of town.
Outlaw Roy Doherty shot a deputy from the hotel window as the man dove for cover.
Deputy Speed was shot and killed as he tried to join another deputy who was using the body of a dead horse for cover.
The prevailing
theory is that Bill Doolin fired the shot that killed Deputy Speed. The deputy who was hiding
behind the dead horse with Speed tried to help a wounded outlaw, but Roy Doherty shot him from the
hotel window. Then, depending on who's telling the story, Jim Masterson captured Doherty by either stunning him with dynamite
or convincing him to come out of the hotel, which was now currently on fire.
Either way, Roy Doherty, alias Arkansas Tom, was the only outlaw captured.
The rest of the gang escaped.
Deputy Speed was killed during the gunfight, and two civilians died during the battle,
a druggist and the 14-year-old boy who unwittingly helped start the chain of events.
In the wake of the deadly shootout, the U.S. Marshals waged a relentless war against the
Doolin-Dalton gang. The common refrain, wanted, dead or alive, was about to be abbreviated.
The Marshals didn't need the second part. Si vous faites vos achats tout en travaillant, en mangeant ou même en écoutant ce balado,
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L'armée américaine ED Nix a organisé un groupe d'armes elite group of manhunters to eliminate the Doolin-Dalton gang.
He recruited 100 deputies to pursue the gang day and night until the job was done.
Bill Tillman was one of the elite, along with fellow deputies Chris Madsen and Heck Thomas.
In May of 1894, a little less than a year after the Ingalls shootout,
Roy Doherty stood trial for his role in killing three deputies in the battle.
Jurors found him guilty of manslaughter, not the more serious crime of murder.
Territorial Judge Frank Dale, who presided over the case, was disgusted. He told Marshal Nix to instruct his deputies to
bring the rest of the Doolin-Dalton gang in, dead. There was no more dead or alive.
The gang was the number one priority, but Bill Tillman already had a full plate.
The newspaper in the small town of Perry bragged that Tillman had made over 150 arrests
and expected him to keep up the good work.
He was responsible for dealing with domestic violence, petty theft, horse theft,
and helping drunks to dry out.
He was referred to interchangeably as the chief of police in both Guthrie and Perry,
or city marshal,
and then of course a deputy U.S. marshal. Tillman did anything dangerous that needed to be done,
including trapping a mountain lion outside Guthrie. He removed a bomb that was lying in
the street in Perry. He risked his life by taking the bomb to a secluded area and setting it off by firing at it from behind a knoll.
But Bill Dalton and Bill Doolin remained his primary focus. Dalton was most recently wanted
for the robbery of a Texas bank on May 23, 1894. It was bold and horrific. Dalton and his crew sent
all the customers and tellers outside to stand in the street and act as human shields.
When the outlaws and the local lawmen exchanged gunfire, the civilians were caught in the middle.
Several were killed or wounded, and only one member of the gang was killed. The rest escaped.
It was almost anticlimactic when Bill Dalton met his end two weeks later.
climactic when Bill Dalton met his end two weeks later. In the early morning hours of June 8,
1894, Deputy Marshals Loss Hart and Selden Lindsey shot and killed Bill Dalton. They cornered him on a ranch in the Arbuckle Mountains in south-central Oklahoma. The death of Bill
Dalton meant that the last of the original Dalton gang was gone, but Bill Doolin and some
trusted lieutenants were still on the loose. Tillman and Deputy Heck Thomas found they worked
well together and began going out on longer and longer trips into Indian territory. They nabbed
whiskey sellers and horse thieves and brought them to Fort Smith for trial. But the reward money for anyone in the Doolin-Dalton crew would be much better,
and crisscrossing the territories let them check in with their friends and sources
about the location of Doolin and his thugs.
Soon enough, Tillman got his chance with an outlaw named Bill Radler.
And yeah, apparently everyone in Oklahoma was named Bill at the time.
William must have been the most popular name in the area.
But Bill Radler was only 22 years old and already notorious.
He was wanted for killing a preacher and wounding a Chickasaw man.
There were also warrants for his arrest from Wichita, Fort Smith, Kingfisher County, and the Chickasaw Nation.
Utah, Fort Smith, Kingfisher County, and the Chickasaw Nation. He was different from most of the other outlaws in the Doolin sphere in that he was educated on the East Coast
and was supposed to have continued in some sort of professional career.
Instead, he got the itch to wander and was drawn to excitement and quick money.
He joined up with Doolin's gang in 1892. In the spring of 1895, Radler and the rest
of the gang robbed the Rock Island train near Dover, Oklahoma. They did the robbery without
Bill Doolin, who was sick and also tending to his wife and new baby. The gang tried to force
open the safe containing $50,000 in Army payroll.
When they couldn't get it open, they robbed the passengers of cash and jewelry.
Deputy U.S. Marshal Chris Madsen and his posse picked up the trail of the outlaws and surprised them around noon.
The marshals killed Bill Blake, nicknamed Tulsa Jack, and scattered the rest of the gang, including Radler. The fear was that
Radler was smart enough and bold enough to continue the gang's tradition of robberies and maybe even
start his own gang. When Marshal Nix learned that Radler was an integral part of the Dover robbery,
he offered up some of his own money as a reward and corralled the best men at his disposal to go after him.
And though Doolin had been quiet lately, Nix knew that if he could get Radler and Doolin,
he would have effectively ended the gang. With that in mind,
Heck Thomas and then Bill Tillman saddled up.
In late August 1895, Deputy Heck Thomas learned that Radler and a couple henchmen were holed up in the Osage Nation in northeastern Indian Territory.
In the fall of 1895, a few months after Chris Madsen's posse nearly captured Radler, Heck Thomas and another deputy were doing surveillance in a small town.
At first, they didn't recognize Radler as he walked around the tiny town because he had shaved off his beard and mustache. The details are lost to history, but somehow Thomas and his posse lost
Radler, though not before Thomas shot the outlaw's hand. Rather than dress the three fingers that were torn up by the bullet,
Radler cut them off with his own pocket knife.
Thomas and his posse picked up Radler's trail again for a few days,
but then lost him.
Thomas and his team were exhausted.
He wired Bill Tillman to relieve him,
and Tillman and his posse took off for the rugged hills of the Osage country.
Tillman had heard that Radler was hiding with an old woman on a ranch. While that was the general
description, Tillman suspected that Radler hid in the woods during the day and came in at night to
eat and sleep. Tillman's posse rode to the ranch, and Tillman confronted
the woman. He demanded to know where Radler was hiding. She confirmed the outlaw had been there,
but she said he'd already left. At that moment, Tillman heard shots fired from the direction of
the barn. Supposedly, one of the bullets knocked his hat off. Tillman spun and plugged three bullets into Radler.
To everyone's surprise, Radler didn't die, at least not right away.
Years later, he died from his wounds.
But for now, Tillman and his posse dragged Bill Radler back to court and sent him to federal prison.
That left just one more big target, Bill Doolin. Doolin was known to
suffer from rheumatism since being shot in the leg by Deputy Chris Madsen back in 1893.
To help with his condition, Doolin traveled to a resort near Eureka Springs, Arkansas,
that was popular because of the soothing powers of its mineral waters.
that was popular because of the soothing powers of its mineral waters.
Reportedly, Tillman tricked Doolin's housekeeper into telling him that Doolin was at the resort.
Tillman and his posse reached Eureka Springs on January 12, 1896,
about six months after they captured Bill Radler.
One of the first people Tillman saw in town was Bill Doolin.
Thankfully, Doolin didn't see Tillman.
Tillman knew it would be frowned upon and instantly suspicious to walk into a resort carrying a loaded shotgun. So he went to a nearby carpenter and asked the man to make a box for the
weapon. Tillman explained to the carpenter how he wanted the box to quickly drop open if he needed the gun.
The carpenter said it would take him about an hour to craft the box.
To kill time, Tillman thought he might as well go for a mineral bath himself.
When Tillman walked into the bathhouse, there was Bill Doolin, lounging with a newspaper.
Tillman quickly walked past the outlaw and pretended not to notice him.
Later, Doolin said he thought Tillman looked familiar but couldn't place him.
He never thought Tillman or any other deputy would have traveled so far to find him.
Tillman had a pistol of some sort hidden on his person, and he decided now was the time.
He wasn't going to wait for the carpenter to finish his project
and risk losing Doolin. Tillman circled back to the room and ordered Doolin to put his hands up.
Then he told the concierge to disarm the outlaw while every other man in the room hurried to get
out. Doolin swore that if his handcuffs and irons were removed, he wouldn't try to escape.
swore that if his handcuffs and irons were removed, he wouldn't try to escape. Tillman took him at his word and warned Doolin that if he did try anything, he would drop the outlaw dead in his tracks.
They left on the next train out of Eureka Springs. As they pulled into Guthrie, Oklahoma,
a crowd of about 2,000 people stood on either side of the tracks and cheered for the man who had captured the King of the Outlaws,
as Doolin was called. It was a glorious moment, but unfortunately the celebration didn't last long.
On July 5th, 1896, after Bill Doolin sat in jail for six months, he and four other prisoners overpowered and disarmed the night guard, locked him in a cell, and then disappeared.
Doolin made his way down to Mexico, but returned when he couldn't stand to be away from his wife and child.
Six weeks later, on August 25, 1896, Deputy Marshal Heck Thomas caught up with him at his father-in-law's ranch. Thomas and
his posse shouted at Doolin to surrender. Instead, Doolin wheeled around and fired once from his
Winchester and three times with his revolver. The posse responded by emptying their guns at Doolin.
He died on the scene, with 20 buckshot wounds to his chest. The king of the outlaws was
now truly done. Unfortunately for Tillman, Oklahoma refused to pay him the reward money
for the capture of Bill Doolin. Even though it was no fault of Tillman's, the outlaw escaped
from jail before trial, which made Tillman
ineligible for the money. Eventually, Heck Thomas received the $1,400 prize and split it between
himself and the members of his posse. In the spring of 1898, the two remaining members of
the Doolin-Dalton gang were killed in shootouts with lawmen. Heck, Thomas and Bill Tillman teamed
up again to bring down the last one, Richard West, in April. With the gang extinguished,
the frontier was called closed. Now, that wasn't really true, but it felt like the end of the Old
West era. In spite of losing out on the Doolin reward money, Bill Tillman prospered.
In 1899, he helped establish a farm that raised thoroughbred horses.
In 1900, Tillman easily won election as the sheriff of Lincoln County, Oklahoma, and was re-elected two years later.
In 1904, toward the end of his second term, he was in New York on political business.
His old friend Bat Masterson, who was a newspaper writer in the city,
introduced him to President Theodore Roosevelt.
They hoped the president might offer Tillman the job of U.S. Marshal of Oklahoma,
which he supposedly offered to Chris Madsen, too.
Ultimately, it went to someone else, but Tillman continued as a deputy, and in 1910,
he won election to the Oklahoma State Senate. In 1915, Tillman went into the new business
of filmmaking with his old boss, E.D. Nix, and his friend, Chris Madsen. They had been playing
around with the idea since 1908, when silent pictures became popular in their rural area.
The trio soon became fed up with the way Hollywood glamorized and romanticized the outlaws
that they had worked so hard to stop. They decided to make movies of how it really was back then,
and formed the Eagle Film Company. The men produced a feature-length film called
The Passing of the Oklahoma Outlaws, which they starred in themselves.
Also in the film was an unlikely guest, Roy Doherty, otherwise known as Arkansas Tom.
He had been in prison since the infamous Ingalls shootout, but he was paroled in 1910, and now he was the only living member of the Doolin-Dalton gang.
Only a few minutes of the film survives, but you can find it online.
And sadly, the story of Bill Tillman doesn't have a happy ending.
On November 1st, 1924, Tillman ran into a young Prohibition agent named Wiley Lynn in Cromwell, Oklahoma.
Lynn's colleagues claimed Tillman accepted bribes
for allowing vice to flourish in town. Tillman's friends said Lynn was the crook. That night,
Tillman and Lynn ended up in a confrontation in Murphy's Dance Hall. There are conflicting
stories about exactly what happened, but the end result was that Lynn shot and killed Bill Tillman.
what happened, but the end result was that Lynn shot and killed Bill Tillman. He was one of the last surviving lawmen of the Old Guard and the Old West, and his second wife Zoe made sure he was
remembered. She published a biography of her husband many years after his death. It certainly
had its share of inaccuracies, but it was one of several books that were published in the 1930s and 40s that
helped reignite the interest in lawmen like Wyatt Earp, Bat Masterson, and the Three Guardsmen.
Next time on Legends of the Old West, it's a series that I've teased a couple times,
and now it's really happening. It's the controversial story of Tom Horn and his role in the Johnson County War.
That's coming up in a couple weeks here on Legends of the Old West.
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$5 per month. This series was researched and written by Julia Bricklin. Original music by Rob Valliere.
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