Legends of the Old West - THREE GUARDSMEN Ep. 4 | Chris Madsen: “Oklahoma Lawman”

Episode Date: August 10, 2022

One of the most dangerous jobs in Oklahoma Territory is that of a U.S. Marshal. After the Doolin-Dalton Gang robs a series of trains, Deputy Marshal Chris Madsen and his posse fought in deadly shootouts to stop the gang once and for all. There were casualties on both sides, but Madsen and the marshals prevailed. Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join To advertise on this podcast, please email: [e-mail] 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

At 9.45 at night on June 1st, 1892, six men robbed a southbound Santa Fe train as it arrived at Red Rock Station in Oklahoma Territory. They supposedly made off with at least $50,000 from a Wells Fargo safe. In today's money, that's about a million and a half dollars. U.S. Marshal William Grimes and two Wells Fargo detectives picked up the outlaw's trail, but then they lost it. It didn't help that the robbers had a two-day head start. Five days after the robbery, Grimes heard that four of the six bandits had been spotted southwest of Guthrie, Oklahoma. The next day, Grimes summoned his top trackers, which included his chief deputy, Chris Madsen, and another lawman named Tillman Lilly. Madsen grabbed fresh horses and the prison carriage, which was basically a big wagon with iron bars that looked like a moving jail cell.

The three lawmen rode all night to reacquire the trail. Early the next morning, Grimes, Lilly, and Madsen found one lone robber. He was so exhausted that he told them the location of the rest of the gang in return for a night of sleep in the prison wagon. Finally, at sundown, the lawmen spotted a pair of thieves riding leisurely about a half a mile ahead. Quietly, Grimes spurred his horse forward and caught up to the two men. He pulled his Winchester rifle and pointed it at their backs. The outlaws quickly separated, and as Grimes chased one, the other took aim at the marshal. But as he did, Chris Madsen, who had been driving the prison carriage, leapt off the wagon.

He shot the horse of the outlaw who was about to kill Grimes, and then he grabbed the outlaw as the man started to fall. In seconds, both outlaws were in custody and joined their friend in the prison wagon. Within a day of U.S. Marshal William Grimes enlisting the help of his chief deputy, Chris Madsen, half the train robbers were in custody. It took a few more weeks for Madsen to track down the last of the four robbers who were seen near Guthrie. None of those four were known members of the most feared crew in Oklahoma, the Doolin-Dalton gang, and the names of the remaining two train robbers never made it into the papers, so their affiliation isn't known. But everyone assumed they were from the notorious Doolin-Dalton gang. Legend has it that the Red Rock job was simply a trial run for a deadly train robbery six weeks

later. That one was definitely orchestrated by the Doolin-Dalton gang, and there would be plenty of others. The people of Indian and Oklahoma territories wanted the gang extinguished by any means necessary, and that job fell squarely on the shoulders of Chris Madsen and the rest of the U.S. Marshals. As a podcast network, our first priority has always been audio and the stories we're able to share with you. But we also sell merch, and organizing that was made both possible and easy with Shopify. sell merch. And organizing that was made both possible and easy with Shopify. Shopify is the global commerce platform that helps you sell and grow at every stage of your business. From the launch your online shop stage, all the way to the did we just hit a million orders stage. Whether you're selling scented soap or offering outdoor outfits, Shopify helps you sell everywhere. They

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Shopify powers 10% of all e-commerce in the U.S. Shopify is also the global force behind Allbirds, Rothy's, and Brooklinen, and millions of other entrepreneurs of every size across 175 countries. Because businesses that grow, grow with Shopify. Sign up for a $1 per month trial period at shopify.com slash realm, all lowercase. Go to shopify.com slash r-e-a-l-m now to grow your business, no matter what stage you're in. Shopify.com slash realm. 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 4, Chris Madsen, Oklahoma Lawman. Chris Madsen's time in the Army had its share of controversy. Besides some tall tales about his heroic actions and extensive travels, he was thrown in military prison for five months in 1881. The reasons aren't clear, but it seems to have had something to do with stealing Army grain. But if he did, he certainly wasn't the only one to do so when soldiers were starving on the plains. Regardless, he was later acquitted.

Madsen spent 15 years in the Army, culminating with a post at Fort Riley, Kansas. In May of 1885, he was promoted to Quartermaster Sergeant. At that time, half the U.S. Army was stationed at Fort Riley to help keep the Cheyenne and Arapaho from leaving their reservation. As Madsen told it, he had barely settled in at Fort Riley when General Nelson Miles sent for him. In October of 1876, Miles was placed in charge of operations against the Lakota, and in an unexpected twist, General Miles didn't want Madsen to hunt or scout or fight. He wanted Madsen to become an army accountant. Miles explained that the financial records of a new outpost were in total disarray, and he told Madsen to get them

straightened out. It turned out that during Madsen's 15 years of service, he proved to have a strong command of math, logistics, and accounting. It took Madsen several months to get the finances back in order, and then, when he went back to Fort Riley, he was promptly arrested for being absent without leave. It isn't clear where the misunderstanding lay, but Madsen wired Miles Miles and the general had him released. At a Christmas party in 1885, Madsen met Miss Margaret Bell Morris. She was nearly 20 years younger, but eventually Madsen won over Margaret's father. They married in 1887. Two children quickly arrived, and he soon realized that his salary of $29 per month from the military was not enough to raise a family. He took advantage of the 1889 land rush in Oklahoma Territory and bought some property near El Reno. By 1891, he had completed a house in the beginnings

of a farm, and he retired from the Army. Madsen was now 40 years old, and he decided to take up an offer from the U.S. Marshal of Oklahoma Territory. That marshal was William Grimes, who was apparently pleased with some freelance accounting work that Madsen had done for him at his office at Fort Smith. Instead of a measly $29 a month, Madsen now earned a very respectable $250 a month, or so he said. Marshals didn't earn a fixed salary, but rather earned commissions based on arrests, delivery of subpoenas, and other tasks. Whatever the case was with Madsen, he happily reported to his post and saddled up. reported to his post and saddled up. On June 2nd, 1892, just hours after the Red Rock train robbery, a newspaper printed a tiny little remark in its gossip section. It said it had received the horrible news that Deputy Chris Madsen was liable to become the successor to Marshal William Grimes.

The article continued by saying that those readers who were familiar with Madsen's past would understand what this meant for Oklahoma. It was a not-so-subtle reference to the fact that plenty of people believed Chris Madsen should not be in law enforcement after his checkered Army career. But Madsen remained a deputy for the time being, and after he helped capture four of the six train robbers from the Red Rock job, the criticism subsided. Truthfully, most law-abiding citizens knew that it was all hands on deck if the Marshal Service was going to take down the biggest threat in the territories.

The Red Rock bandits might not have been part of the crew that was the biggest threat, but everyone knew who that crew was. The Doolin Dalton Gang. If there was ever going to be peace in Oklahoma, the gang had to be stopped. About a year earlier, in September of 1891, Bill Doolin's desperados teamed up with the Dalton brothers to rob several banks throughout the region. The Dalton gang organized a string of heists that netted them tens of thousands of dollars, even if they couldn't seem to hold on to much of it.

Like many outlaws, the members of the Dalton gang drank and gambled away their money nearly as fast as they stole it. But at least they were good at avoiding capture. nearly as fast as they stole it. But at least they were good at avoiding capture. As the 1890s progressed, it seemed like three deputies became the most adept at tracking and capturing or killing members of the Dalton gang. Those deputies were, of course,

Heck Thomas, Bill Tillman, and Chris Madsen. They all took decidedly different paths to law enforcement in Oklahoma, and the one that was least likely to become a lawman was Madsen. But he more than made up for his inexperience decidedly different paths to law enforcement in Oklahoma, and the one that was least likely to become a lawman was Madsen. But he more than made up for his inexperience when the trio started hunting the remainder of the Dalton gang in earnest. Madsen may have caught a couple of loose associates of the gang when he rounded up the Red Rock robbers, but it certainly wasn't enough to deter the gang

from trying again. On July 15, 1892, three Daltons, Bill Doolin, and four other men planned to rob a train at Pryor, a small town 45 miles east of Tulsa. But Bob and Grant Dalton used to work in the area, and friends told them that the train might have deputies hiding on board. The gang quickly revised its plans and picked Adair Station not far away. The outlaws were bold. At about 9 p.m., they rode up and waited for the train, which was a little late. To pass the time, they ransacked the station and took anything of value. When the train finally rolled in at about 9.45, the gang confidently boarded. They captured members of the train crew with no resistance and ordered them to obey or they would be shot. Then the gang marched the crew down to the express

car. As one robber threatened the express agent to open the safe, one of the others fired shots toward the town to discourage people from trying to stop the robbery. There wasn't much in the safe, so the gang turned to the passengers. When they were done robbing the passengers of cash and jewelry, they started loading it into a stolen spring wagon. Most historians estimate that the take was a very respectable $17,000. It all happened so fast that the railroad detectives and Indian guards on board the train didn't realize what was going on until it was too late. They scrambled out onto the platform and fired at two bandits who were in view. Of course, the outlaws immediately shot back. A detective took a bullet in the shoulder.

One of the guards was wounded in the leg, but they all survived, though unfortunately the same couldn't be said for a couple unlucky citizens. Two stray bullets found their way into a drugstore in town. The bullets hit two doctors who were just sitting there minding their own business. One died within hours, and the other was permanently disabled. It wasn't the first killing on the resume of the Dalton gang, but it added more heat from law enforcement. Heck Thomas, for one, was hot on the gang's trail. Ultimately, the gang tried to rob two banks at the same time in Coffeyville, Kansas. The disastrous raid ended the original lineup of the Dalton gang.

The disastrous raid ended the original lineup of the Dalton gang, and for reasons that were never fully explained, Bill Doolin was not at the Coffeyville raid on October 5, 1892. Some witnesses swore they saw six men during the robbery, not just five, and in 1896, Doolin himself told several lawmen that he actually did ride along on the raid. But whatever happened with Doolin that day in early October, in the aftermath, he gathered the remaining associates and took over as the leader. In doing so, he placed himself squarely in the crosshairs of Chris Madsen, Heck Thomas, and Bill Tillman. Thomas had played a major role in forcing the gang to try a crazy

robbery, and he would be there at the end to take down the most prominent member. But in the meantime, Chris Madsen started slowly but surely chipping away at the gang's power. Madsen was in Guthrie, Oklahoma during the Coffeyville raid. His office received a telegram with the details, and he immediately passed the information on to the press. As word spread throughout Guthrie, the last Dalton brother, Bill Dalton, appeared in Madsen's office to ask if the report was true. Madsen believed that Bill Dalton and Bill Doolin had been waiting near Guthrie for the rest of the gang to finish the raid.

But it doesn't seem like Madsen took any action against Bill Dalton at the time. Less than a month later, Madsen might have regretted it. The new version of the Dalton gang robbed a bank in the tiny town of Spearville, Kansas, a few miles up the road from Dodge City. This lineup would soon be known as the Doolin-Dalton gang, and it featured Bill Doolin, Bill Dalton, George Bitter Creek Newcomb, and a newcomer named Oliver Yantis. Yantis had the unfortunate honor of being the target of Chris Madsen's investigation. Madsen was at a place called Fort Supply when he received a telegram that said the gang was headed his way. He was determined to capture or kill as many of the criminals as he could. He gathered some friends who were also former 5th Cavalry men and gave chase.

Unfortunately, the gang had a head start that was insurmountable, so Madsen disbanded his posse and returned to Guthrie. A few days later, the sheriff of Ford County, Kansas, where Dodge City and Spearville are located, came to Guthrie and asked Madsen to help him try again. The sheriff wanted to catch the new guy, Oliver Yantis, at the very least. Yantis had separated from the rest of the gang and he was vulnerable. By now, it was early November 1892, and Madsen had learned that Yantis was also wanted for the holdup of a Santa Fe train near Wharton, Oklahoma, which was not to be confused with a train robbery at Wharton a year earlier. Unfortunately for lawmen in the territories, certain railroad stations continued to be irresistible targets. Madsen started investigating, and he discovered that Yantis had a sister who lived in the area.

Madsen thought there was a chance that Yantis would be hiding with his sister. Madsen, the county sheriff, and a few others quietly moved into position near the house. They hid behind a stone fence and spent hours waiting to see if Madsen's hunch would pay off. A little after daybreak, it did. Yantis came out with a sack of feed for his horse in one hand and a pistol in the other. When he was within 20 steps of the lawman, Madsen yelled out,

Up with your hands! Yantis raised his hands and the six-shooter with it. He leveled the gun at Madsen and fired. At the same time, Madsen squeezed the trigger of his Winchester rifle. Yantis missed, but Madsen's bullet hit its mark. Though as Madsen told the story, his first shot didn't do much to Yantis. Madsen said Yantis had a wad of paper money from the Spearville bank robbery folded into his breast pocket. The money slowed the bullet down to the point where it broke the skin but did very little damage. However, it did enough to give Madsen's fellow lawmen the half second they needed to fire their weapons. The buckshot from their double-barrel shotguns

tore into Yantis and knocked him to the ground, but he kept firing on his way down. Just then, the outlaw's sister ran out of the house and begged the officers to let her brother live. Madsen told her that he had no intention of killing Yantis if the young man laid down his gun and surrendered. She went to her brother and took his gun. He was still alive, but fading fast. The posse rushed him to a local physician, but the doctor couldn't save him. Oliver Yantis died at about midnight, cursing and threatening revenge until his last breath. That was one down and several more to go. The Doolin-Dalton gang continued to plague Oklahoma territory for the next four years, and the worst, for the lawmen at least, was yet to come. the most savings on your shopping. So join Rakuten and start getting cash back at Sephora, Old Navy, Expedia,

and other stores you love. You can even stack sales on top of cash back. Just start your shopping with Rakuten to save money at over 750 stores. Join for free at Rakuten.ca or get the Rakuten app. That's R-A-K-U-T-E-N. That's R-A-K-U-T-E-N. In late May of 1893, Madsen returned to his office in Guthrie, Oklahoma from a trip to Washington, D.C. He met with government officials to show them their system for paying marshals in the territories was a total mess. Thanks to his thorough record-keeping, Madsen managed to get nearly $80,000 in back pay

to distribute to 150 lawmen back home. In their eyes, he was probably a hero. But Madsen's satisfaction at the accomplishment was short-lived. About a week after he got home, the Doolin-Dalton gang held up a Santa Fe train in Kansas and stole $1,000 in silver. According to a few sources, including his own words, Madsen fired a shot at Bill Doolin during the pursuit, which severely wounded him in the foot. But the gang of four or five robbers managed to get away. After that robbery, it was decided that a change of leadership was needed in the U.S. Marshal's office in Oklahoma Territory. On July 1, 1893, Evett Dumas Nix took the oath of office as the U.S. Marshal of Oklahoma

Territory. His name is usually abbreviated E.D. Nix, so that it just looks like Ed Nix. And at 32, he was the youngest man ever assigned to the position. Though his predecessor William Grimes had only been on the job for a few years, he might have welcomed the break. All in all, Grimes had done a good job. He'd organized Oklahoma's first comprehensive law enforcement system. He'd organized Oklahoma's first comprehensive law enforcement system. He'd employed more than a hundred deputies, including Madsen, Heck Thomas, Bill Tillman, and other notables.

He brought some semblance of law and order to the territory. For decades, it had been a haven and a hideout for thousands of criminals. The problem was, Oklahoma still needed a lot more law and order. Besides the run-of-the-mill horse thieves, bigamists, and whiskey runners, the territory was still held hostage by the Doolin-Dalton gang and several imposters. Marshal Nix was smart enough to keep Madsen, Tillman, Thomas, and many other men on as deputies, even though they'd been hired by Grimes. There was no substitute for experience, and those men had it in spades. Marshall Nix probably had high hopes for a full sweep of the Doolin-Dalton gang on September 1st, 1893, exactly two months after he was hired. He organized a posse to go

to the town of Ingalls, a known haven for criminals, to capture them once and for all. A devastating gunfight broke out, and all of the outlaws escaped with the exception of one who was nicknamed Arkansas Tom. The full story of the gun battle in Ingalls is coming up in episode 6, but suffice it to say, it was a tragic day for law enforcement. Three men and a 14-year-old boy were killed that day, and none of them were members of the outlaw gang. The boy was just a bystander who was caught in the crossfire. Madsen vowed to do his part to bring Doolin and Dalton and all of their followers to justice. Because of the nightmare in Ingalls, Marshal Nix organized an elite group of about 100 deputies. Its sole aim was to wipe out the Doolin-Dalton gang.

Madsen, Heck Thomas, and Bill Tillman were in the elite group, and it's believed that this is when people started calling them the Three Guardsmen. They were under great pressure from Marshal Nix, who was under a mountain of pressure himself as the new young hotshot marshal. The gang didn't let up. It continued to strike in the territories and parts of Kansas and Missouri. In the spring of 1894, Nix sent out a new directive to his elite group of deputies. In it, he said to bring them in alive, but dead if necessary. Two months later, he amended his instruction to remove the first part. At that time, Arkansas Tom, whose real name was Roy Doherty,

received a prison sentence that the marshals felt was a slap in the face. Doherty was the only outlaw who was captured during the Ingalls shootout, and a jury convicted him for manslaughter instead of murder for his role in killing three deputies. In the wake of the verdict, the territorial judge who presided over the case told Marshal Nix to revise his orders. He instructed Nix to tell his deputies to bring the Doolin-Dalton gang in dead. Period. On April 3rd, 1895, the gang, without Bill Doolin, held up a Rock Island train near the village of Dover, which was less than 30 miles from Chris Madsen's office in Guthrie, Oklahoma. When the gang was unable to open the safe that held $50,000 in Army payroll money, the bandits robbed the passengers instead.

Madsen and his posse took a special train to Dover. After trailing the gang for most of the morning, he suggested the posse split into two groups. Madsen led one west along the Cimarron River. Deputy William Banks and six other men followed a trail that the bandits didn't even bother to hide. Banks and his men spotted the outlaws at about noon. They were barely 60 yards away in a grove of blackjack trees, resting themselves and their horses. The deputies grabbed their rifles, dismounted, and shouted for the gang to surrender. Bill Doolin's right-hand man, Tulsa Jack Blake, was standing guard. Blake had participated in many of the gang's robberies. There was a big reward on his head, especially since he was a

key figure in the Ingalls shootout. He fired the first shot at the lawman, which alerted his sleeping comrades. In a fierce gun battle lasting almost 45 minutes, more than 200 shots were fired. Midway through the melee, Blake tried to flee on another outlaw's horse. Deputy Banks took careful aim with his rifle and fired, and killed Tulsa Jack Blake instantly. Ultimately, two more bandits were wounded, but the rest managed to escape, though their days were truly numbered. Over the next year, deputy marshals wiped them out. Marshal Nix asked his deputies to keep quiet about who killed whom during the pursuit of the Doolin-Dalton gang, because the threat of retribution was so high.

A few months before Madsen's posse killed Tulsa Jack Blake, the gang assassinated Fred Hoffman, the treasurer of Dewey County and a U.S. Commissioner for Indian Territory. Hoffman had provided some damning information that led to the arrest of several gang members. In retaliation, the gang shot him in the head, killed his horse, and threw them both in a ditch. By the end of 1896, Madsen was happy to tell reporters that his friend Fred Hoffman had been avenged. One by one, the outlaws fell. Madsen captured Alfred's son, who had participated in the murder. Son was headed for prison. George Red Buck Waitman was shot to death by a posse of citizens.

Jim Harpold was captured by deputies and rangers and received a life sentence in Leavenworth Prison. He had company when fellow outlaw Bill Radler joined him the same year. Dan Dynamite Dick Clifton was shot and killed, either by Madsen's posse or a brave citizen. The details are murky, so it's hard to tell. And then finally, there was Bill Doolin. His role as the leader of one of the last big outlaw gangs also ended in 1896. But we'll save that story for the next two episodes when we focus on the third of the three guardsmen, Bill Tillman. Just two years after the destruction of the Doolin-Dalton gang, Chris Madsen mourned the death of his wife, Margaret,

who passed away after a long struggle with tuberculosis. Maybe trying to distract himself from the grief, he returned to his military roots. He joined Theodore Roosevelt's Rough Riders as quartermaster sergeant. After that, at the age of 60, when most men of his era had long since retired, Madsen was appointed U.S. Marshal for the state of Oklahoma, though his job was mostly bureaucratic by that point. He retired from active duty law enforcement in 1913, but he still worked as a guard, a court bailiff, and a superintendent at the Union Soldiers Home. In 1915, Madsen formed the Eagle Film Company with his good friends Bill Tillman and former Marshal E.D. Nix. But the lure of the entertainment industry was brief. From 1918 to 1922,

he served as a special investigator for the governor of Oklahoma. He tried to re-enlist in the army to fight in World War I, but for some reason the army thought that a man who was in his late 60s might not be ideal for combat overseas, and it rejected his request. He lived the rest of his days in Guthrie, Oklahoma. On January 9th, 1944, at the age of 92, Chris Madsen passed away at a Masonic home in Guthrie

while recovering from a broken hip. He saw more of the world and lived the lives of 10 men, and he was laid to rest in Yukon, Oklahoma. Next time on Legends of the Old West, we'll start the complex story of the third guardsman, Bill Tillman. He spent most of his adult life as a lawman, but he was constantly in trouble with the law. We'll begin with his time in Dodge City, working with legends like Wyatt Earp and Bat Masterson, and that's next week on Legends of the Old West. Members of our Black Barrel Plus program don't have to wait week to week for new episodes.

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