LEGENDS OF THE OLD WEST | Outlaws Ep1: “Doc Middleton”

Added: 2026-05-05

[00:00:12]The 19-year-old kid who walked into the Texas State Prison at Huntsville in 1870 was probably booked under the name James Middleton Riley. If he were, there's no guarantee that that was his name. His first name might have been James, but it also might have been David. His surname might have been Riley and it might have come from his mother. It also might have been Middleton and it might have been neither of those. The most common story is that he was from Bastrop County, Texas, just east of Austin and about 2 hours from Huntsville. He also might have been from Mississippi. He went to prison for something. Obviously, the two crimes that are most often cited are murder or horse theft. Given the reputation he soon established and the earliest reference to the crime, it was probably horse theft. The story goes that he grew up in Bastrop County, Texas in the 1850s and 1860s. And he stole his first horse when he was 14, sometime around 1865.

[00:01:13]He probably got caught for stealing another one in 1870. And that was why he went to Huntsville, the towering fortress of a prison that was nicknamed the walls. Nine years later, infamous killer John Wesley Harden would be a guest at the facility. 50 years after that, a young thief from Dallas named Clyde Barrow would do 6 months at Huntsville before he was transferred to a prison farm. The stint in prison interrupted his blossoming romance with a girl named Bonnie Parker. In 1870, James Middleton Riley's prison sentence also interrupted a young romance. He had married sometime before he was caught, though virtually no information survives about his first wife. The pattern of uncertainty continues with the year in which James decided he was done doing time at Huntsville Prison.

[00:02:07]In 1874 or 1875, James escaped Huntsville Prison. The rumor was that he somehow secured an old shovel and tunnneled his way out of his cell and under the wall of the prison.

[00:02:21]When he was free, he ran north for 800 m to the state of Iowa. More than likely, he stole horses along the way to carry him to Iowa because he was arrested for stealing horses in Iowa almost immediately after he arrived. He spent a year in an Iowa jail and was apparently released in the spring of 1876.

[00:02:41]From there he drifted west to Nebraska where he changed his name to David C.

[00:02:45]Middleton which was much closer to the name he would be known by in the years to come. He signed on with the Pratt and Ferris Cattle Company. The company supplied beef to Fort Randall in Dakota territory and the two Lakota reservations in northwestern Nebraska.

[00:03:01]Those were the original Redcloud Agency and Spotted Tail Agency before both were eventually relocated to what became the Pineeridge Reservation in southern Dakota territory just above the border with Nebraska. That reservation and the region just south of it called the Sand Hills in northern Nebraska would be the birthplace of the legend of the man who would be known as Doc Middleton.

[00:03:26]James Middleton Riley, then calling himself David C. Middleton worked as a nighttime cattle herder for Pratt and Ferris for the second half of 1876.

[00:03:36]And he might have continued with the outfit, and his life might have turned out differently if it hadn't been for a fateful encounter in a saloon in southern Nebraska in January of 1877.

[00:03:48]After that, he would be on the run again, but he would only run to the northern part of the state. He would go back to the Sand Hills and the area near the Lakota agencies where he would become arguably the most prolific horse thief in American history from Black Barrel Media. This is Legends of the Old West. I'm your host, Chris Whmer, and this season we're telling the stories of six outlaws. They're horse thieves, bank robbers, train robbers, and gunfighters. This is episode one.

[00:04:26]Doc Middleton, king of the horse thieves.

[00:04:42]In mid January 1877, the cowboys with a herd of Pratt and Ferris cattle stopped the herd overnight in the town of Sydney, Nebraska. Sydney was a railroad town on the dusty plains of western Nebraska, just above the Colorado border. The town was founded in 1867 by the Union Pacific during the construction of the transcontinental railroad. Like many stops on the line, the US Army built a fort at Sydney to protect the railroad.

[00:05:10]And like dozens of places across the West, where there was a pairing of a fort and a town, there was a combustible atmosphere.

[00:05:18]In a tiny speck of a place like Sydney, Nebraska, there wasn't much law. But what passed for it was busy on the night of January 13th, 1877.

[00:05:29]That night, which was probably bitterly cold on the raw plains of Nebraska, David C. Middleton walked into Joe Lane Saloon for warmth and entertainment.

[00:05:39]Middleton was 26 years old, and he would have looked like many of the other cowboys, freight haulers, and drifters.

[00:05:46]And of course, soldiers were also in the saloon that night, and that was how the trouble started. There are accounts which say it was soldiers night in the saloon, and only soldiers could dance with the ladies. Apparently, a woman who had danced with a soldier ended up paying a little too much attention to Middleton after the dance. Private James Keith of Company C of the Fifth Cavalry wasn't happy about the interaction, and that was about all it took to start a fight in an Old West saloon.

[00:06:20]Keith was bigger and stronger than Middleton, but when the fight broke out, it seemed like Middleton had the upper hand in the early stages. Then it may have turned into a brawl as other soldiers joined the fry. Keith turned the tables on Middleton and started beating the cowboy badly. As Middleton absorbed the punishment and began to falter, he reached for his pistol. He drew the gun and fired a single shot.

[00:06:45]The bullet dropped Private Keith. David C. Middleton was quickly arrested and thrown in the town's primitive wooden jail.

[00:06:53]As word spread through Sydney that a cowboy had killed a soldier, the news provoked the typical response. A lynch mob assembled with the goal of making sure the cowboy didn't see the sunrise.

[00:07:04]In the jail, whether or not Middleton knew about the lynch mob, he wasn't planning to stick around to see how justice would turn out. The historical record is frustratingly vague on the details of his escape, but he quietly slipped out of the jail and vanished into the darkness. Maybe he pried up the floorboards or found a way to unlock the cell or received help from a sympathetic person. However he did it, he was two for two on jailbreaks in the past 3 years. From Sydney in the southwest corner of Nebraska, he ran west to Cheyenne, Wyoming. It was only 90 mi down the rail line, but it was enough for the moment. He may have found a job at the ranch of a man named William Irving, but if he did, the job didn't last more than a couple months. It was later reported that Middleton stole 35 horses from Irving's ranch and fled east back to Nebraska and the Sand Hills region that would be his base of operations for the next few years. The Sand Hills region of Nebraska is huge.

[00:08:06]It's the size of the states of Maryland and Vermont combined. Much of it looks like classic grass land of the prairie, and it is, but it's also unique because the grass rises up through sand dunes instead of directly from the soil.

[00:08:20]There's plenty of water from streams and an underground aquafer, which feeds the area. And from the sand hills, Middleton was perfectly situated to steal horses from the red cloud and spotted tail agencies.

[00:08:38]The US government had changed the locations of the Lakota agencies twice before 1877.

[00:08:44]And in October of that year, the agencies moved to their final destinations. They moved from northwest Nebraska to south central Dakota territory right above the Dakota Nebraska border and straight north of the Sand Hills. There the agencies would eventually form the heart of the Pineriidge Reservation.

[00:09:04]As far as is known, Middleton had been hiding in the Sand Hills since the spring of 1877 when he reportedly stole 35 horses from the rancher William Irving.

[00:09:15]Throughout the second half of the year, Middleton gathered a gang of horse thieves and started to build an empire.

[00:09:21]And it was likely during that time that everyone started calling him Doc. He may have acquired the nickname as a cowboy with the Prattton Ferris Freight Company. There were stories of him nursing injured cowboys and a few horses, which was an easy way to earn the nickname Doc. Another way, and probably more likely, was that Middleton became an excellent horse doctor. In the outlaw slang of the Old West, a horse doctor was not a veterinarian. A horse doctor was someone who was great at changing the brands on horses or doctoring them to hide the fact that the animals were stolen. So in 1877, Doc Middleton formed a gang called the Pony Boys, and they stole horses at an absolutely epic rate.

[00:10:10]The estimates were astounding. Over a 2-year period from roughly the summer of 1877 to the summer of 1879, the stories say Doc Middleton and his gang stole 2,000 to 3,000 horses. Their primary targets were the herds at the Lakota agencies. They stole the animals in bunches, sometimes upwards of 150 at a time. The gang drove the horses deep into the Sand Hills region. The Pony Boys maintained a chain of ranches in the Niaber Valley where the horses could graze on the prairie grass. Then the thieves sold the animals to farmers and ranchers who were always interested in horses at good prices and who didn't ask too many questions.

[00:10:53]The gang roamed through Nebraska, Iowa, Colorado, Wyoming, and Dakota territory, and they were equal opportunity thieves.

[00:11:01]Their most frequent targets were Native American horse herds. But they stole from the army, the Union Pacific Railroad, and ranchers when the circumstances allowed. As the gang became more prolific, the loss of horses on the planes became something close to a crisis. Stealing horses was a serious crime in and of itself, but the loss of the animals wre havoc on the transportation of men and supplies. Doc Middleton's gang had to be stopped. The US government, the Union Pacific Railroad, and the Wyoming Stock Growers Association teamed up to bring him down.

[00:11:38]The association would become infamous during the Johnson County Range War of the 1890s, but in the late 1870s, it was just getting started.

[00:11:47]It had been formed in 1872 and it had grown significantly by 1877 when Doc Middleton stole 35 horses from William Irving. Irving was a well-connected rancher north of Cheyenne. And when Doc returned to the area the following year, 1878, and stole 40 more horses, the chase was on.

[00:12:08]The association assigned range detective William Lyens to catch Doc Middleton.

[00:12:14]Lyens tracked Middleton and two associates from Cheyenne, Wyoming, 130 mi east to Julesburg, Colorado.

[00:12:22]There, Lychens captured Doc Middleton and gang member Ed Scurry.

[00:12:28]The detective transported the men farther east to Sydney, Nebraska, and deposited them in the same jail from which Doc had escaped 2 years earlier.

[00:12:37]And again, if there was ever a case of history repeating itself, this was it.

[00:12:41]Doc escaped from the Sydney jail again.

[00:12:44]Like before, few details are known, but Doc Middleton and Ed Scurry made it out and hurried back to their sanctuary in the Nyber Valley in northern Nebraska.

[00:12:54]The US government, the Union Pacific, and the Wyoming stock growers were furious. The railroad put a $1,000 bounty on Doc Middleton's head, and the government and the stock growers brought in more help to rid the country of its most prominent horse thief and escape artist.

[00:13:18]Newspapers across the country picked up the growing story of the ghostly thief of the Plains. The man had been caught a couple times, yes, but no jail could hold him for long. The newspapers declared that a full account of his prolific villain would fill a large volume. Despite the $1,000 bounty on his head, Doc Middleton remained hidden in the sand hills. As the calendar turned from 1878 to 1879 and winter turned to spring, there was no sign of the bandit.

[00:13:50]At that point, the Department of Justice took more aggressive action. The reward wasn't enough for people to turn in Doc Middleton. So the law needed a manhunter. William Henry Harrison Llewellyn was a deputy US marshal in Omaha, Nebraska. He was the same age as Middleton, 28, and he was educated and wellraveled.

[00:14:10]By the spring of 1879, the government was so fed up with Doc Middleton that the US Attorney General Charles Dvers personally offered Deputy Marshall Llewellyn a special commission as an agent of the Justice Department.

[00:14:25]Llewellyn would have one mission, stop Doc Middleton once and for all.

[00:14:30]Llewellyn accepted the assignment and he quickly recruited a man named LP Hazen to join the effort. Hazen was an ex-convict who had ties to the Pony Boys gang. He could get close to the gang when the time was right. Deputy Marshall Llewellyn and LP Hazen traveled the Nyab River Valley for more than a month as they investigated the gang. By the end of June 1879, Llewellyn was confident that he had enough evidence to convict Middleton and his top associates. The bigger problem was the physical act of catching them. To that end, Llewellyn offered Doc Middleton a pardon in order to lure him into a trap.

[00:15:15]LP Hazen and possibly Deputy Llewellyn visited Middleton repeatedly. The basic deal was that Doc Middleton would turn himself in and work with law enforcement to catch other outlaws. Then he would receive a pardon and he would not go back to prison. Middleton was obviously skeptical and he required a lot of convincing, but he eventually agreed to the deal. The men set a date, July 20th, 1879, to finalize the agreement. At the appointed time, Llewellyn and Hazen rode up to the meeting spot in a remote area of northern Nebraska, likely near the Nyerber River. Doc Middleton arrived with his top lieutenant, William Kidd Wade. The four men stayed on their horses and talked about the deal points for a brief period of time before Doc realized something was wrong. Something in the grass nearby drew his attention.

[00:16:10]Range detective William Lyens, who had arrested Doc the previous year, was hiding in the brush with his rifle at the ready. Lychens and Llewellyn had coordinated an ambush and everyone opened fire. Lyens let loose from his hiding spot. Llewellyn and LP Hazen opened up at short range. Doc drew his pistol and returned fire. The gunfight was brief but fierce as the men tried to dodge bullets and control their horses.

[00:16:38]Hazen was hit three times. Llewellyn suffered grazing wounds to his arm and hand and Doc took a bullet to the abdomen that exited his back. He was essentially gutshot and by that point all the men were scattering.

[00:16:53]Doc's partner, Kid Wade, seemed to have escaped without injury, but they all galloped away from the sight of the fight. Doc made it to the campsite that he and Kid Wade had used before the meeting. Details are sparse, but it seemed to be in one of the many small canyons along a branch of the Niaba River. At the campsite, Doc would have been bleeding badly and would have been in tremendous pain. One of the stories said his wife, Mary Richardson, his second wife, found him and started to nurse him. Her father helped and together they kept Doc alive while a posi of lawmen and soldiers scoured the area to find him. The posi led by Deputy Marshall Llewellyn eventually found Mary's father and threatened him with hanging if he didn't reveal Doc's location.

[00:17:41]Grudgingly, the father revealed the location of the camp and the posi captured Doc Middleton on July 29th, 9 days after the gunfight.

[00:17:50]4 days later, on August 2nd, the New York Times splashed a headline across the front page which read, "The captured outlaw chief, details of the arrest of Doc Middleton, crimes of which he is accused." 6 weeks later in midepptember Doc was convicted of stealing 35 horses and sentenced to 5 years in prison.

[00:18:17]Doc Middleton was 28 years old and still weak from his gunshot wound when he walked into the Nebraska State Penitentiary in Lincoln in September 1879.

[00:18:28]In prison, he finished his recovery, regained his strength, and re-evaluated his career as the king of the horse thieves. When he walked out three years and nine months later with a reduced sentence for good behavior, he was a reformed man. His second wife, Mary Richardson, unofficially divorced him while he was in prison. Basically, she declared herself divorced and moved on with her life. Doc apparently married her younger sister and they lived in Stewart, Nebraska for a short time. Then they drifted to Gordon, Nebraska, a small town in the state's northwest corner. In Gordon, Doc opened a saloon which became popular as a tourist attraction for people who wanted to see the legendary horse thief. And at about the same time, Doc's former lieutenant, Kid Wade, met a worse fate. William Kidd Wade was captured in the tiny town of Lamar's, Iowa in February 1884.

[00:19:25]Law men transported him halfway across Nebraska to the village of Longpine before vigilantes took Wade from the lawman and lynched him from a telegraph pole in the neighboring village of Basset. Kid Wade was 21 years old. The following year, Doc Middleton did something that he and Wade probably would have considered unthinkable during their heyday as horse thieves. He put on a badge.

[00:19:54]Sheriff John Riggs of Sheridan County, Nebraska, asked Doc Middleton to be a deputy, and Doc accepted the job. For a few years, Doc held dual roles as saloon operator and deputy sheriff. And those years were relatively quiet for Doc Middleton. He and his wife raised two boys and a girl, but sadly the girl died when she was 5 years old. Sometime after that tragic event in 1890, Doc's fairly normal life received a jolt of excitement. For nearly 20 years, Buffalo Bill Cody had been building an entertainment empire, which was anchored by his world famous Wild West show.

[00:20:34]Sometime between 1890 and 1892, Cody asked Doc Middleton to join the production. Doc spent a few weeks and maybe upwards of a few months adding his celebrity status to the show as the former king of the horse thieves. It was a short gig and then Doc went back to running saloons. But in 1893, Doc had a reunion of sorts with Buffalo Bill when Doc participated in the event that cemented his legacy. It was a long-d distanceance horse race that was never supposed to happen. That year, Chicago hosted the World's Fair. The city built sprawling fairgrounds that were nicknamed the White City because of their gleaming stone buildings. The World's Fair in Chicago became infamous in later years as the story of confessed serial killer HH Holmes grew to fantastical proportions. Holmes began his murders at his notorious castle in the Englewood neighborhood of Chicago in the years leading up to the fair. The horse race that drew in Doc Middleton was sanctioned somewhat after the fact by Buffalo Bill Cody. Organizers of the World Fair would not let Cody include his Wild West show in the official proceedings. So Cody rented an empty field near the fairgrounds and built his own venue for his show. At the same time, John G. Maher, the clerk of Daw County, Nebraska, triggered a media avalanche.

[00:21:59]Mah was an admitted prankster. He loved to send outlandish stories of the Wild West to Eastern newspapers. Most of the stories were complete fiction. He just got a kick out of making Easterners believe crazy things about the West. In March of 1893, John Maher sent a story to Eastern newspapers about a wondrous event that was being coordinated by the tiny town of Shadron, Nebraska. Why Shadron, Nebraska of all places? because of course that was where John Maher lived and worked as the clerk of Daw County.

[00:22:33]Mar's story said the town fathers were organizing a 1,000mi horse race from Shadron to Chicago in conjunction with the World's Fair. Mar said 300 cowboys were gathering in Shadron to take part in the once-in-a-lifetime Pony Express style event. As John Maher's story spread, reporters from all over the country requested interviews with the organizers in Shadron, which illuminated one small problem with the story. The whole thing was a joke. It was a hoax.

[00:23:04]There weren't 300 cowboys lining up in Shadron because there was no race. At least not yet.

[00:23:16]The great cowboy race, as it would be called, sounded like a great idea, and people were excited to see it, which placed the town fathers of Shadron in a difficult position.

[00:23:26]They held an emergency meeting to discuss the crisis. If they admitted the story was a hoax, they would be the laughingtock of the nation. But the alternative was to actually do the race.

[00:23:38]And how in the world were they going to organize a 1,000mi horse race on short notice? As luck would have it, one of the civic leaders of Shadrid was close personal friends with the greatest showman of the era, a man who knew exactly how to organize that kind of event. The civic leader contacted Buffalo Bill Cody, and Cody made the event real. With Cody's contribution to the effort, he ensured that the race would finish at his Wild West venue, and that would be an incredible promotional opportunity for his show. He and the organizers in Shadron collected $1,500 in prize money. The Colt Firearms Company donated a gold-plated, ivory handled revolver, and Montgomery Ward donated its best saddle. With Buffalo Bill on board, the race was a go. It would start on June 13th, 1893 at the Blaine Hotel in Shadran. Among the rules, the riders could only use two horses during the 1,000mi journey. That rule on top of the race in general caused fury among humane societies who argued that it was barbaric to force the horses to participate in the grueling race. Despite that and other protests, the race went ahead as scheduled.

[00:25:01]On June 13th, spectators crowded the streets of Shadran. Nine riders assembled at the starting line with their pairs of horses. The local favorite was 42-year-old Doc Middleton, who was easy to recognize with his signature long beard that would have perfectly qualified him as a guitarist for Zezy Top if he had been born 60 years in the future. Doc rode a horse called Geronimo with his second horse Bay Jimmy in tow. A fire chief raised a revolver, fired it into the air, and the race was on. Doc and the other riders pushed their horses through the sand hills of northern Nebraska and then to the flatter terrain in eastern Nebraska.

[00:25:42]They crossed the Missouri River into the rolling hills of Iowa and then into the nearly identical scenery of western Illinois. And that was where things started to go wrong. The riders and horses had been blasted by sand and wind. They had been drenched by rain.

[00:25:58]The riders had been in the saddle 16 hours a day, and the horses had been in motion nearly all of those hours. In Iowa, Doc's primary horse, Geronimo, went lame, and Doc was forced to leave the animal behind. In western Illinois, his second horse, Bay Jimmy, went lame, and Doc officially dropped out of the race. He eventually made it to the finish line, but he finished last. Ahead of him, the race ended with frenzy and controversy. On June 27th, 14 days after the race started, 10,000 people cheered at the finish line in front of Buffalo Bill's Wild West venue for the man who arrived first. Buffalo Bill declared John Barry the winner of the Great Cowboy Race and presented him with $500 and the Montgomery Ward saddle. Over the next two days, the other eight riders crossed the finish line. Doc Middleton arrived last on June 30th, but the crowd cheered nearly as loud as it had for the winner. And by that time, controversy was swirling around John Barry. When the organizers learned Barry had finished first, they disqualified him. Barry had played a role in mapping the secret route that the riders were supposed to use for the race, which meant he had an advantage. and the organizers accused him of riding on a train for part of the way. Shadron named the second place finisher, Joe Gillespie, the winner, and gave him $200 in prize money and the goldplated Colt revolver.

[00:27:30]The same type of split decision happened with some of the riders, but not Doc.

[00:27:34]Doc Middleton received between $50 and $75 as a consolation prize for finishing last.

[00:27:41]The race that started as a joke became a riveting spectacle and then a fiasco.

[00:27:47]And the real winner in the whole thing was predictably Buffalo Bill Cody. He put in between $500 and $1,000 in prize money. And he would have made that back many times over.

[00:28:05]After the great cowboy race of 1893, Doc Middleton went back home to Gordon, Nebraska. As the years passed and the new century approached, he drifted from Gordon to towns like Edgemont, South Dakota, and Ardmore, Nebraska.

[00:28:20]With the passing of the Old West era, Doc Middleton became something of a relic. As telephones and electric lights and motor cars became more common in the early 1900s, Doc found himself in places which didn't feature many of those modern contraptions.

[00:28:37]In 1913, in the railroad town of Orange Junction, Wyoming, south of Douglas, he made the gamble that cost him his life.

[00:28:46]He opened a type of saloon that was known as a blind pig. It was an illegal bar that sold liquor without a license, and it wasn't in business for very long.

[00:28:56]In early November, two patrons got into a knife fight in Doc's saloon. On November 5th, Sheriff Albert Payton arrested Doc for operating a blind pig.

[00:29:07]The fight wasn't Doc's fault, but the venue was. The crime was a misdemeanor, but it still commanded an order to shut down the saloon and pay a fine or spend a few days in jail. Doc didn't have the money to pay the fine, so he went to jail.

[00:29:28]Doc Middleton was 62 years old, and while he sat in what was probably a tiny, squalid cell in a town that wasn't much more than a railroad junction, he contracted a sickness called Iicipilus.

[00:29:41]It was nicknamed St. Anony's Fire for good reason. In short, irrius is a bacterial infection that attacks the skin and the tissue underneath it.

[00:29:51]Pockets of skin became red and angry with inflammation and swelling. The pain was agonizing and Doc's skin felt like it was on fire. With modern medicine, a week of antibiotics could clear it up.

[00:30:04]In a 1913 frontier jail, it was a death sentence.

[00:30:10]The source of the infection isn't known, but Doc probably caught it in the jail cell, though it could have happened during the knife fight, or maybe in combination with the old bullet wound in his gut from 1879.

[00:30:22]Regardless, the infection raged. His fever spiked and pneumonia filled his lungs.

[00:30:29]At some point, he was transported 12 mi up the road to Douglas, Wyoming, and installed in what was called at the time a pest tent or a pest house for people with serious infections.

[00:30:41]He lingered, racked with pain and sickness, for about a month.

[00:30:46]Sometime in December, James Middleton Riley died, mostly anonymous, in the pest tent in Douglas. Some records say the date was December 13th. Others say it was December 27th.

[00:30:58]Doc Middleton, the king of the horse thieves, was buried by the county in Douglas Park Cemetery. At the time, his grave was unmarked, but in 1976, a family member purchased a simple flat headstone, which is engraved with the name David Doc Middleton. Today, it marks the spot of Doc's final resting place in the Douglas Park Cemetery.

[00:31:31]Next time on Legends of the Old West, it's the short and violent career of Crawford Goldsby, better known as Cherokee Bill. He lived just 20 years.

[00:31:41]His time as an outlaw may have covered only a blazing 2-year period, but it may have started when he was as young as 12.

[00:31:48]He robbed banks, trains, and stage coaches. He killed at least two people and maybe as many as 13.

[00:31:57]Cherokee Bill's story starts next week on Legends of the Old West.

[00:32:16]To binge all the episodes of a new season and to listen to every episode of the podcast with no commercials, subscribe in Apple Podcasts or sign up through the link in the show notes or on our website blackarmedia.com.

[00:32:29]This series was researched by Mandy Whmer and written by me, Chris Whmer.

[00:32:33]Original music by Rob Valier. Thanks for listening. Hallelujah.