Legends of the Old West - THREE GUARDSMEN Ep. 2 | Heck Thomas: “Tracking the Dalton Gang”

Episode Date: July 27, 2022

The Dalton Gang plagued Oklahoma Territory in the early 1890s. After the disastrous Coffeyville Raid, the gang reformed as the Doolin-Dalton Gang, with Bill Doolin at the helm. The U.S. Marshals hired a legion of deputies, including Chris Madsen and Bill Tilghman, to bring down the gang, and Heck Thomas dealt the final blow when he cornered Bill Doolin in 1896. 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

On November 29, 1887, Deputy U.S. Marshal Heck Thomas arrived in the city of Macalester in what was then the Choctaw Nation in Indian Territory. He had three wagonloads of prisoners and several posse men with him. They'd been plagued by heavy rainstorms and needed to stop at a small town to let the wagons dry out. Waiting for Thomas was a telegram from his boss. It told of a horrible situation. It seemed that two days earlier, two fellow deputies had been sent after a gang of horse thieves. The gang was led by a man named Dave Smith. In addition to stealing horses, he sold liquor in Indian territory. Both were serious offenses at the time.

The two deputies on his trail were Frank Dalton and James Cole. It didn't take long for Dalton and Cole to figure out where Smith was camping. Dalton was the first to reach Smith's tent. As he did, a volley of shots burst out of it. One of the bullets passed through Dalton's chest. Cole quickly pulled Dalton a few feet away and returned fire. When Smith ran out of his tent, Cole shot him dead. As Smith's criminal companions poured out behind him, they shot Cole in the arm and the leg.

Miraculously, Dalton was able to fire some shots from his Winchester as he lay a few yards away. Though Cole was badly wounded, he was able to retreat thanks to the cover provided by Dalton. Cole eventually recovered, but Frank Dalton did not. Someone in Smith's outlaw gang shot him while he lay on the ground bleeding from the chest wound. Heck, Thomas was horrified as he read the telegram that described the murder of his friend and fellow deputy. The telegram also said that one of Smith's accomplices was hiding there in the Choctaw Nation. Thomas decided to stay with his prisoners, but he sent two deputy marshals from his posse to get the accomplice. A day later, the two deputies snuck up on the young criminal at daybreak. When they shouted at him to hold up his

hands, the outlaw pulled out a hidden revolver. He shot one of the two deputies three times and killed him instantly. When word got back to Thomas that another friend was dead, he felt guilty and mad as hell. Two of Heck Thomas' friends had been killed by the same gang. Both were deputy marshals, and their murders set off a chain reaction that put the Dalton family, an outlaw named Bill Doolin, and Deputy Marshal Heck Thomas on a collision course. 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. 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,

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pour leur envoyer des gens magasinés et Rakuten partage l'argent avec vous sous forme de remise. Téléchargez l'application gratuite Rakuten et ne manquez jamais un bon deal. Ou allez sur rakuten.ca pour en avoir plus pour votre argent. C'est R-A-K-U- Société Radio-Canada Chris Wimmer, and this season we're telling the stories of the Three Guardsmen, a trio of U.S. Marshals who neutralized some of the worst criminals in the Old West. This is Episode 2,

the second half of the Heck Thomas story, Tracking the Dalton Gang. In 1886, not long after bringing down the notorious Lee brothers in Texas, Heck Thomas was appointed a deputy U.S. marshal. He was just shy of 36 years old. He moved his family to Fort Smith, Arkansas, and worked under the hanging judge, Isaac Parker. Over the next seven years, Thomas earned a reputation for being one of the most efficient deputies working the lawless land of

Indian Territory. On his first assignment, he apprehended eight murderers, a bootlegger, a horse thief, and several other hard cases. But over time, he noticed some things about some of the other deputy marshals. They could be just as lawless and brutal as the men and women they arrested. A few of Thomas' colleagues purposefully turned their prisoners loose, pretending they had gotten away. There was no rule stopping them from making more money by going after the outlaws again and charging for their efforts. But even those who cheated the system could have trouble making a living as a deputy. The financial reward for putting your life in danger as a lawman in and around Indian territory was not substantial. Until 1898, Western district marshals didn't get a straight salary. They earned their living on a fee system. An aggressive deputy like Bass Reeves could earn up to $10,000 per year,

but the majority of deputies rarely made more than about $500 per year. And the temptation to participate in crimes they were tasked with stopping could prove to be too much. That was exactly what happened with the brothers of Deputy Frank Dalton. When Dalton was shot and killed in November of 1887, his brothers Bob and Gratton, better known simply as Gratt, left their homes in California. They made their way east to pay their respects to their brother,

and they took advantage of his good name. They got jobs as deputy marshals for the Western District. Soon, Bob and Gratt sent for their younger brother, Emmett, and got him a job as a guard in the Fort Worth jail. It isn't clear how well Heck Thomas knew the Dalton brothers at the time, if at all, but it is true that he thought the world of Frank Dalton. He thought Frank was as honest and as upright as they came. He thought Frank was as honest and as upright as they came. But in the aftermath of Frank's murder, Thomas had other problems.

Chasing murderers and thieves over 75,000 square miles meant Thomas was away from home more often than not. His wife, Belle, reached her breaking point. She divorced him and moved back to Texas. And she was probably smart to do so. The 1880s and 1890s were particularly deadly for U.S. Marshals in the Western District. It seemed like in the months surrounding Frank Dalton's murder, it was open season on Marshals and Indian peace officers alike. Some of the assassinations became nationwide news.

Some of the assassinations became nationwide news. Cherokee Police Captain Sam Sixkiller was ambushed and murdered on Christmas Eve, 1886. Five months later, notorious Cherokee outlaw Ned Christie was accused of ambushing and killing Deputy Dan Maples. Maples' successor, William Fields, was killed just a few months later. An Oklahoma newspaper tallied 15 Western District deputies who had been killed over the previous two years. In June of 1888, Heck Thomas was shot twice by whiskey thieves named the Purdy Brothers. Some men, like Thomas, thrived on adventure and danger, and worked extra hard to make a living wage. Others naturally wondered why the hell they repeatedly put themselves in harm's way without the guarantee of a certain level of income. Sometimes it could take months for a deputy's pay to come through for a particular job.

Deputies had to be thrifty and plan ahead for such occasions, and not all of them possessed the ability. So it wasn't surprising that a few might be tempted to flip to the other side of the law. And that was what happened with the Dalton brothers. By all accounts, the three younger Dalton brothers were competent lawmen. They weren't outstanding, but they were decent. They could have continued as guards or possemen or deputy marshals for the rest of their professional lives. They could have learned a trick or two from some of the more seasoned men like Bass Reeves or Heck Thomas. But the brothers were young and impulsive. By midsummer 1889, the gossip around Fort Worth said the

Daltons had gone wrong. It seems Bob and Grat had already earned reputations for drinking on the job. In 1888, Bob killed a burglar, which was a problem because Bob was not actually sworn in yet. Grat became known as someone who viciously harassed people of color, and he also had a gambling problem. Brother Emmett graduated from jail guard to posse man, but he lacked the bravado of his older brothers. And then Bob got into even more trouble by taking whiskey into the Osage country. He got caught, and depending on who you believe, Bob got fired or he quit. Either way, he claimed the government cheated him out of nearly $900 in wages. He was bitter, and he and his brothers were about to cross the line.

Heck, Thomas was working in the Cherokee country for much of 1889 and 1890. When he heard the rumors about the Daltons, he was inclined to ignore them. But then he heard stories directly from two other deputies, with whom he was close friends. He relied on their word. They told Thomas about how Emmett and Bob stole about 20 horses and a pair of mules in the Osage Nation. Long story short, the Dalton brothers were clumsy and they got caught. All three brothers officially lost their jobs as deputies. On September 6, 1890, warrants were sworn out for Bob, Gratt, and Emmett Dalton,

charging them with horse stealing. Over the next few days, Gratt and another man stole 30 more horses. Citizens in Claremore, Indian Territory, arrested Gratt and turned him in. At his preliminary hearing, no evidence could be found that connected him directly to the crime, but there was enough evidence to tie brothers Bob and Emmett to it. When Grat was released, he went to Tulsa, most likely looking for work. Heck Thomas found him in Tulsa, and according to one historian, asked Grat to give up the location of his brothers, so that Heck could serve their warrants. Not surprisingly, Grat refused. The next day, Thomas heard that Grant left for California, where he and his siblings had once lived. Thomas figured Emmett and Bob probably fled as well.

But just to be safe, the marshal's office kept eyes on the homes of Dalton relatives in Oklahoma. While Thomas waited for news about the location of the Dalton brothers, he stayed in Tulsa. of the Dalton brothers, he stayed in Tulsa. He'd recently received a commission to work out of the newly established federal court in Muskogee, which was only 35 miles away. But there was another reason to stay as well. Four years earlier, he met the daughter of a minister. Her name was Maddie Mowbray, and she was only 15 years old at the time. Now she was 19, and the two decided it was time to get married. Heck Thomas was 41. He was attending court in Muskogee when another marshal handed him a flyer. It was dated March 26, 1891, and it explained what the Dalton brothers had been up to. Six weeks earlier, Bob, Emmett, Gratt, and another brother, Bill, attempted to

rob a Southern Pacific train in Tulare, California. They failed, thanks to the bravery of the express messenger. But the train's firemen died from bullet wounds the next day. The railroad, Wells Fargo, and the state of California offered a reward for the Dalton brothers. Detectives tracked the four outlaw brothers to a tiny town in the desert north of Los Angeles. Then, it seemed the brothers jumped on an eastbound train and disappeared. Bill Dalton reached out to the press and law enforcement in California. He admitted that he had helped his brothers get out of the state and hide. But he said he did it only because they were wanted for horse stealing in Indian territory.

He claimed they had nothing to do with the attempted train robbery. Bill demanded that the authorities lift the robbery charges against Bob and Emmett. If they did, Bill said he could get them to surrender. But law enforcement refused to let Bill communicate with his brothers unless a deputy went with them. Bill insisted on going alone. He told them, The boys are desperate.

They have over 800 rounds of ammunition and will kill any man who goes with me. hundred rounds of ammunition and will kill any man who goes with me. One of Heck Thomas' bosses found out that Bob and Emmett had come back to what was now Oklahoma Territory. They had to be desperate, because they risked spending the night at their mother's house, a place that was well known to lawmen. For the next month or so, the Dalton brothers stayed one step ahead of citizen posses. The brothers were chased more than once by farmers who were angry about livestock they stole along the way. The Daltons were a prime example of why so many criminals like to hide out in Indian and Oklahoma territories. They knew every way to hinder the pursuit or avoid the marshals because

they had once been marshals. They knew, for example, that deputies only got paid for mileage if they managed to collar the suspect or suspects. They didn't get paid for trying. And they had to use their own money for their horse and food. They would not get reimbursed unless they actually captured their quarry. Furthermore, a deputy could not pursue a criminal outside his own district without permission from the marshal in another district. But Heck Thomas was one of the exceptions to the rule. Several head marshals had worked out a flexible commission system. That way, they could give a select few lawmen permission to chase and capture outside their primary district.

Thomas was trustworthy, respectful, and careful. Besides Indian territory, Thomas was allowed to chase the Daltons in the unoccupied portion of Cherokee land. And so, in late April 1892, Thomas set out with his friend Burrell Cox and a gifted tracker named Tiger Jack of the Creek Indian Police Force. It didn't take long for them to find fresh horse tracks left by the Daltons near the Arkansas River. The trail was only three or four hours old. Tiger Jack and Burrell Cox were anxious to keep after the Daltons and what appeared to be at least two others. But Thomas looked around and realized they would soon cross into another jurisdiction, one for which he did not have a commission. Cox blustered and threatened to go on alone. They were so close, but Thomas was firm. He would not chase criminals in another marshal's territory,

though he did have an idea. Thomas and his two companions set off for the nearest telegraph station. They wired the marshals who supervised Indian Territory and Oklahoma Territory. They explained the situation and requested permission to pursue the Daltons into the Pawnee Nation. The marshal in charge of Oklahoma Territory welcomed the request, and on May 2, 1892, he made Heck Thomas a deputy marshal for Oklahoma Territory. Heck Thomas now had permission to track the Daltons just about anywhere in what is modern-day Oklahoma. And the commission came at the right time, because one week later,

the Dalton gang held up a train 35 miles north of Guthrie, Oklahoma. The Daltons learned that a large shipment of cash headed for a Guthrie bank was on an evening train from Texas. They convinced a few accomplices to join them in making some quick money. They cut eye holes into red handkerchiefs and tied them on as masks. At about 11 p.m., when the train chugged into the water station at Wharton, Bob Dalton and a man named George Bitter Creek Newcomb jumped into the cab. They trained their Winchesters on the firemen and the engineer and ordered them to run the train a half a mile south. Emmett Dalton and a man named Charlie Bryant fired shots over the car to scare the passengers who were trying to look outside. And then, much like Sam Bass had done 13 years earlier in Texas, Bob Dalton marched the engineer and fireman to the express messenger car.

He ordered the messenger to open the door. When the man refused, Bob held a pistol to the engineer's head and yelled that he would blow his brains out. The messenger pleaded for his life and the life of the engineer. He explained that he couldn't open the safe even if he wanted to. The combinations were wired ahead to other stops on the line, and it could only be opened there. The excuse might have fooled the average robber, but it didn't fool Bob Dalton. He had been a deputy marshal, and he knew how the system worked.

His temper flared, and he snarled at the messenger and shot beneath his feet. Terrified, the poor man opened the safe, and the Dalton gang made off with about $400. After the robbery, the gang went on a spree. They held up a railroad north of Wagoner, Oklahoma. They held up a railroad at Red Rock, Oklahoma. They hit another railroad at Adair Station in the Cherokee Nation, and then a bank in El Reno, Oklahoma. The reward for their capture and conviction jumped to $40,000, equivalent to over a million dollars today. By now, the newspapers were fond of pointing out that the Dalton brothers' mother, Adeline,

was an aunt of Cole and Jim Younger of the famous James Younger gang. During the Dalton spree, Cole and Jim, along with her brother Bob, were on year number 18 of their prison sentences in Minnesota after the disastrous Northfield raid. Down in Oklahoma, few people tried to chase the Daltons. The outlaws had graduated to murder, killing several passengers and lawmen during their robberies. Heck, Thomas was one of the men who stepped up to accept the challenge of stopping the gang. Two more were Chris Madsen and Bill Tillman. Like Thomas, they were deputy marshals in the territories.

Together, Thomas, Madsen, and Tillman became known as the Three Guardsmen. They came from very different backgrounds, but they were all about the same age. Before the Dalton gang plagued the region, the lawmen interacted regularly to trap other criminals. Sometimes it was just in passing, sometimes they worked on the same effort. But by the end of the 19th century, the three guardsmen were credited with apprehending or neutralizing 300 criminals in Oklahoma. But it was the Dalton gang that really solidified the working relationship between the three men. And the work became all the more difficult in 1891 when another major player joined the gang. Bill Doolin's first encounter with the law was on July 4th. Originally from

Arkansas, Doolin worked as a ranch hand. He was easy to spot. He was six feet two inches tall, but weighed only 150 pounds. He had reddish hair, blue eyes, and a mustache beneath a crooked nose. On that 4th of July holiday, Doolin and some cowboy friends decided to celebrate by throwing a beer party near Coffeyville, Kansas. The problem was, Kansas was a dry state at the time. It might have still worked out okay, but when a group of deputies arrived and began pouring out the beer, Doolin and his friends pulled out their six-shooters. They shot and wounded two of the deputies. For Doolin, any chance of going back to an honest profession was gone. In a few short months, he would team up with the Dalton gang, or was left of it anyway. On October 5th, 1892,

the Dalton brothers and their accomplices tried to cash out by robbing two banks at once. The hasty robbery was poorly planned, largely because the gang was on the run and trying to stay one step ahead of Heck Thomas. For nearly a year and a half, the Dalton gang had terrorized Oklahoma. They'd mostly done train holdups, and they'd managed to avoid Oklahoma lawmen, including Bill Tillman, Chris Madsen, and Heck Thomas. But it was Thomas of whom they were most afraid in the fall of 1892. So they decided to do one big score,

one that would make them enough money to leave the territory for a long time. Deputy Marshal Heck Thomas had doggedly tracked the Daltons after their train robbery in July 1892. He located their hideout in the Osage Nation and discovered their campsite. It was about 20 miles south of Coffeyville, where they had once lived. Thomas was at the campsite when he got word that the Daltons had struck not one, but two banks in Coffeyville. The result was a running gunfight in the middle of town that left eight men dead.

eight men dead. Grat Dalton led two of the gang's members into the C.M. Condon Bank. Emmett and Bob Dalton went into the First National Bank. Once inside, the outlaws in both banks pulled their guns on customers and employees. The outlaws tried to disguise themselves by wearing fake beards and mustaches, but they didn't fool anyone. People on the street recognized the Daltons as they walked into their respective banks. A quick-thinking employee at the Condon Bank managed to delay opening his safe. The extra ten minutes gave townspeople outside the time they needed to hurry to the hardware stores. They grabbed guns and ammunition and engaged in a firefight with the outlaws. For a full account of the Coffeyville raid, please go back to Season 1, Episode 1 of the podcast. We did that story in the very first

episode because it's one of my favorites. When the gun battle was over, the people of Coffeyville had ended the Dalton gang. 21-year-old Emmett Dalton was the only outlaw still alive, and he was reportedly wounded 23 times. But the town's victory came with a price. Four Coffeyville defenders died in the raid. Bill Doolin didn't participate in the robbery, but he did take center stage now that Bob and Grat Dalton were gone and Emmett was headed for prison. He took the few remaining members and some new recruits and formed his own gang. Eventually, they became known as the Wild Bunch, a name that is also associated with the gang led by Butch Cassidy and the Sundance Kid.

Over the next few years, the Doolin-Dalton Gang, as it was also called, robbed banks and trains throughout Kansas, Indian Territory, and Oklahoma Territory, and got involved in a number of shootouts with law officers, including the infamous gunfight in the small town of Ingalls in Oklahoma Territory. You'll hear the full story of that event in Episode 6 of this series. In January of 1896, Deputy Marshal Bill Tillman managed to capture Bill Doolin at a resort in Arkansas. Unfortunately, the night before Doolin's trial began, he and several inmates escaped from prison. Heck, Thomas learned Doolin was hiding at his father-in-law's homestead

between Stillwater and Tulsa, Oklahoma. On the night of August 24, 1896, Thomas and nine deputies, including his son Albert, surrounded the place. When Doolin came out of the barn, Thomas called for him to surrender. Not surprisingly, the desperado shot at Thomas. In return, the lawmen shot and killed Bill Doolin. The fatal shot was thought to have come from Heck Thomas' shotgun, and he is usually credited with finally ending the most notorious outlaw in Oklahoma territory in the waning days of the Old West era. By the end of 1898, all of the remaining members of the Doolin Dalton gang were dead. Most were killed in shootouts with lawmen. Heck Thomas had tracked most of them. The rest were tracked and eliminated by Chris Madsen and Bill Tillman and other posses,

and those stories will play out in future episodes. As the century drew to a close and Oklahoma territory was fairly tamed, Heck Thomas became the first chief of police in Lawton, Oklahoma. The new job probably seemed a lot less exciting than tracking the likes of Sam Bass, the Lee brothers, and the Doolin-Dalton gang. But Thomas had one more chance to relive some thrills. In 1908, he starred in a silent film called The Bank Robbery. It was directed by his good friend and former colleague, Bill Tillman, who was already frustrated by Hollywood's exaggerated portrayals of real events. Heck, Thomas passed away four years later in 1912, but his spirit lives on in pop culture. Heck's life and adventures helped inspire scores of films and TV episodes.

Next time on Legends of the Old West, we'll continue to hear more about Heck Thomas, but we'll shift most of the focus to Chris Madsen, as Madsen goes from a cavalryman who fought Native Americans on the Northern Plains to a lawman who chased bandits on the Southern Plains. 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. They receive the entire season to binge all at once with no commercials and exclusive bonus episodes. Sign up now through the link in the show notes or on our website, blackbarrelmedia.com.

Memberships begin at just $5 per month. This series was researched and written by Julia Bricklin. Original music by Rob Valliere. Copy editing by me, Chris Wimmer, and I'm your host and producer. If you enjoyed the show, please leave us a rating and a review on Apple Podcasts or wherever you're listening. Check out our website, blackbarrelmedia.com, for more details and join us on social media. We're at Old West Podcast on Facebook, Instagram, and Twitter. And you can stream all our episodes on YouTube.

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