Legends of the Old West - OUTLAWS Ep. 6 | “Doolin Daltons: Dead Outlaws”

Episode Date: April 23, 2025

After the Battle of Ingalls in 1893, the Doolin Dalton Gang is on borrowed time. They perform a few more robberies, but then, one by one, gang members fall to bounty hunters or the U.S. Marshals.  Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial. For more details, visit our website www.blackbarrelmedia.com and check out our social media pages. We’re @OldWestPodcast on Facebook, Instagram and Twitter. On YouTube, subscribe to LEGENDS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage. Learn more about your ad choices. Visit megaphone.fm/adchoices

To support sustainable food production, BHP is building one of the world's largest hot ash mines in Canada. Essential resources responsibly produced. It's happening now at BH was becoming a little less wild. 30 years of westward expansion after the Civil War brought sweeping changes to the frontier. Most of the old legendary outlaws were dead or had moved on to new phases of their lives. Railroads crisscrossed the west, and telephones were starting to replace the telegraph in a few places. By 1890, the federal government's census officially declared the frontier gone.

The declaration was a little ambitious because it was not gone in the Kansas-Oklahoma region. The Dalton Gang, one of the last prominent outlaw gangs of the West, became headline news in May of 1891. But the gang's crime spree, for all its headlines and craziness, only lasted a year and a half. Four core members were killed in the Coffeyville raid in October 1892 and a fifth was captured and sent to prison. Less than a month afterward, Bill Doolin, one of the early members of the Dalton gang, picked up the pieces and continued the spree. Three members of the new gang called the Doolin-Dalton Gang,

also known as the Wild Bunch, robbed a bank in the tiny town of Spearville, Kansas. Seven months later, members of the gang hijacked a train outside Cimarron, Kansas. Three months after that, came the big showdown in the village of Ingalls, Oklahoma. On September 1, a posse of lawmen, led by a group of deputy U.S. Marshals, confronted at least six outlaws in Ingalls.

During a fierce firefight, multiple people died, including three deputy marshals, but all of the gang members survived. One was captured and sent to prison, but the rest remained free. They only waited four months before going back to work. On January 3, 1894, in the small town of Clarkson, Oklahoma, gang members Charlie Pierce and George Waitman robbed a general store. Twenty days later, members of the gang robbed the Farmer's Citizens Bank in Pawnee, Oklahoma. Six weeks after that, they robbed a train near Woodward, Oklahoma. That made three robberies in three months

to begin the new year of 1894, and they had no plans to slow down. ["The Old West"] 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 infamous outlaws Charlie Bowles, better known as Black Bart, Dirty Dave Rudabot, and the Doolan Dalton Gang. This is episode 6, The Doolan Dalton Gang, Part 2 of 2. Dead Outlaws

On April 1, 1894, three weeks after the Woodward train robbery, Bill Dalton and George Newcomb, nicknamed Bitter Creek Newcomb, rode into a small settlement called Sacred Heart, Oklahoma. They headed for a shop that was owned by a man named William Carr. Carr was a former deputy U.S. Marshal with a somewhat dubious legacy. Like a number of lawmen before and after him, rumors circulated that he sometimes flirted with criminality and spent time with known outlaws. In the past, he had beat charges for murder and arson. But by 1894, Carr was generally considered an upstanding citizen, and he was now a shopkeeper. Bill Dalton and Bitter Creek Newcomb entered Carr's store with a purpose that is still

up for debate. Some said they just wanted to buy feed for their horses, but then Carr recognized them as notorious outlaws. Others claimed they intended to rob the store. Either way, Carr drew down on them, and the outlaws drew it nearly the same time. Pistols blazed in the store, and Bill Dalton shot the former marshal in the stomach. But Carr kept fighting. He succeeded in forcing the two bandits out of his store. He shot Bitter Creek in the shoulder and continued to fire at them as they leapt onto their horses

and galloped out of town. Remarkably, Mr. Carr survived his wound, but others would not be so lucky. Bill Doolin, Bill Dalton, and five other members of the Wild Bunch rode into southwest city Missouri on May 10, 1894. The gang had not yet ventured into Missouri, but this excursion was memorable. The seven outlaws were heavily armed, and they wore masks to cover their faces. The gang dismounted, and they tied up their horses adjacent to the AF Alt Bank on Main Street. Two outlaws stayed with the horses, and two others took up lookout positions. Bill Doolan, Bill Dalton, and another gang member marched into the bank. Within 10 minutes, they had stuffed

thousands of dollars into sacks. They took two bankers hostage and backed out of the bank. They moved slowly across Main Street to the horses, and the sight of masked men with guns, sacks of money, and hostages drew plenty of attention. Citizens raised the alarm, and they started firing at the Doolin-Dalton gang. A gun battle erupted on Main Street, despite the fact that the outlaws were using hostages as shields. When the robbers made it to their horses, Bill Doolin ordered the hostages to run. Then the seven outlaws began firing madly into the street, the shops, and the alleys. As the outlaws charged out

of town, they encountered stiff resistance. A deputy U.S. Marshal and the city marshal assembled people on both sides of the street and ordered them to fire at the fleeing bandits. Two outlaws were hit as they rode through the gauntlet, and Bill Doolin was lucky to survive as buckshot sliced through the air next to his head. All of the outlaws made it out of town alive, and they stole at least $3,000, but they left a hell of a scene behind them. The town had been shot up, and several people lay wounded on the ground. One of the wounded, a former state senator, died from his injuries four days

later. Authorities in Oklahoma shuddered at the news of the raid across the border in Missouri. Later that month, Territorial Judge Frank Dale held a meeting with U.S. Marshal Evette Nix in Guthrie, Oklahoma. Judge Dale had conducted the trial of Roy Doherty, aka Arkansas Tom, the only gang member who had been arrested at the Battle of Ingalls. Dale had sentenced the young outlaw to 50 years in prison, and the judge had reached his breaking point with the lawlessness and the killing. Marshall Nix was coordinating the manhunt for the Doolan-Dalton gang, and he wrote in his autobiography that Judge Dale said, Marshall, this is serious. I have reached the conclusion that the only good outlaw is a dead one. You will instruct your deputies to bring in dead outlaws in the future. That

will simplify your problem a great deal and probably save some lives. The Southwest City robbery was the beginning of the end for the Doolan-Dalton gang. It was the last successful robbery that featured core members of the Old Wild Bunch. After that robbery, for reasons that remain elusive, Bill Dalton recruited three new men and decided to conduct a robbery without anyone from the old gang. On May 23, 1894, just 13 days after the Southwest City robbery, Bill Dalton and his three associates rode into Longview, Texas. Dalton's partners were Jim Wallace and two brothers named Jim

and Judd Knight. They robbed the first National Bank of Longview and stole about $2,000 worth of banknotes and coins, but they also found themselves in a deadly shootout. Jim Wallace was killed, and so were two citizens of Longview. Three more were wounded, including the city marshal. After another harrowing escape, Bill Dalton and the Knight brothers split up. Judd and Jim Knight found themselves in another shootout three years later. Judd was killed and Jim was captured and sent to prison for the Longview robbery. After Longview, Bill Dalton hid with relatives near Ardmore, Oklahoma. For a couple weeks, it seemed like Bill would get away with the heist. But then he used some of the stolen money to buy a wagon and supplies, and that led

the US Marshals to his hideout. A posse of nine lawmen rode into Ardmore. The Marshal who led the posse learned who bought the supplies and where he went. On June 8, 1894, the posse reached the cabin where Bill Dalton was hiding. The lawmen surrounded the cabin and by all accounts they wanted Dalton alive. But US Marshal Nix had also issued an instruction to the deputy US Marshals who became known as the three guardsmen, Heck Thomas, Chris Madsen, and Bill Tillman, which said of the gang members, bring them in, alive if possible, dead if necessary.

Bill Dalton was surrounded by a posse, and he had no chance of winning a fight with nine lawmen. So he decided to make a run for it. He jumped through a window and sped through a patch of corn to escape. As he ran, the posse shouted for him to stop. Bill Dalton raced through the green corn stalks and disregarded the command. The men of the posse opened fire and shot and killed Bill Dalton. In the cabin, there was a woman who claimed to be his wife, Jane. She confirmed the identity of her husband. The deputy marshal who led the posse sent a telegram to his superiors and informed them, Have got one of the Longview bank robbers.

He was killed while resisting arrest. Positive proof, he is Bill Dalton. Jane Dalton took her husband's body to California for burial, and he was interred at Turlock Memorial Park Cemetery in an unmarked grave. That made three Dalton brothers, Bill, Bob, and Gratt, killed in the past two years and one in prison, Emmett. After Bill Dalton's death, all nine of the lawmen in the posse were indicted for murder, but none of their cases went to trial. Bill Dalton's death was a harbinger of what was to come for the rest of the wild bunch.

After all the robberies the gang had committed and all the shootouts it had experienced, only two members had been killed, Oliver Yantis and Bill Dalton. The rest were still alive and free, though that was about to change in a hurry. The gang had just two more robberies in it before time was up. Neither worked out as planned, and then it was open season on the most wanted men in the country. Texanna, Oklahoma was a nondescript hamlet on the eastern edge of the territory, about 60 miles from

Fort Smith, Arkansas, and the feared judge, Isaac Parker. Today, the community sits near the shores of Lake Ufala. But in 1894, the lake was 70 years away from creation through a dam on the Canadian River. As Texana was about to learn, even the smallest towns can be targets for robbery. Six outlaws, led by Bill Doolin, rode into town on December 19th, six months after Bill Dalton was killed. As they had done many times before, some kept a lookout while others entered a store. Inside they found a defiant store clerk.

Outside they found resolute townsfolk. And according to most accounts, the gang had to flee with just $20 in cash. It was a paltry sum, and the lackluster raid seemed to cause a fissure in the wild bunch. For almost four months, the gang did nothing. And when the outlaws materialized again, they were without their other namesake, Bill Doolin. Maybe he had lost faith in the gang, or maybe the gang had lost faith in him, but the remaining outlaws wanted $50,000 of army payroll that was rumored to be on the Rock Island train in central Oklahoma. The small town of Dover sits on the Oklahoma Plains north of Kingfisher,

a Dalton Gang hotspot, and west of Guthrie. The Chicago, Rock Island, and Pacific Railroad ran through town, and on April 3, 1895, the gang stopped the train to steal the Army payroll. An attendant on one of the cars tried to stop the bandits from boarding, but the outlaws shot him and severely wounded him. The robbers found the safe, which reportedly held the payroll, but they also found they had no way to open it. Apparently, they didn't bring dynamite and couldn't find any other way to open the safe, so they abandoned it.

The outlaws resorted to walking through the train cars and taking personal items from the passengers at gunpoint. When the men had collected enough loot, they hurried off the train, jumped onto their horses, and rode northwest. But they didn't ride nearly fast enough or far enough. The US Marshals received word of the robbery, and Deputy Marshal Madsen assembled a posse. The men boarded a train and arrived in Dover the following day. Madsen and his men easily found the trail of the outlaws. The lawmen rented or bought horses and started the pursuit. The gang members only made it about 25 miles northwest of Dover,

near the settlement of Ames, before the posse caught up to them. The Marshals ordered the gang to surrender, but the gang responded with the opening salvo of a shootout. For 45 minutes, the outlaws and the Marshals engaged in a vicious firefight. The Marshals couldn't overwhelm the gang, and the gang couldn't force the Marshals to quit. With the situation at an impasse, Bill Blake, better known as Tulsa Jack, tried to make a run for it. The Marshals cut him down with ease.

Soon after Blake fell dead, two more outlaws were wounded. At that point, the gang members decided they would have to take a chance on an escape, and somehow they made it. They escaped the posse and left Tulsa Jack Blake behind as a macabre trophy for the lawmen. That was another gang member down. Tulsa Jack made three in the past year and a half. Two were dead and one was in prison, and from that point forward, the attrition would happen much faster. The Doolin-Dalton gang feared on the southern plains as the wild bunch was done.

From now on, it was every man for himself. For George Newcomb and Charlie Pierce, it wasn't technically every man for himself. They often worked as a pair, and they were two of the longest-serving members of the gang. They had joined the Dalton Gang in its earliest days, and they had immediately joined Bill Doolin when the old Dalton Gang died in Coffeyville, Kansas. After the narrow escape from Deputy Marshal Chris Madsen's posse, Newcomb and Pierce headed for the friendly confines of the Dunn Brothers Ranch in Payne County, Oklahoma.

The Dunn Brothers, five of them, were bounty hunters who had also dabbled in rustling and robbing in the past. They existed in a gray area between outlaws and lawmen, though they probably leaned a little more toward the outlaw side. The Dunn brothers also had a sister named Rose, and she was the sweetheart of George Newcomb. Newcomb wanted to lay low while in the loving arms of his sweetheart, and he hoped he could collect some money that he believed the Dunn brothers owed him. Charlie Pierce likely just wanted a safe place to hide. As it happened, the two fugitives would find none of those things at the Dunn Brothers Ranch. George Bitter Creek Newcomb and Charlie Pierce rode their horses up to the ranch

on May 2, 1895, one month after they escaped Chris Madsen's posse. The Dunn Brothers were waiting, and not with a warm welcome. As the outlaws drew near the ranch, the Dunn brothers jumped out of their hiding places and launched an ambush. The brothers opened fire before either outlaw could defend himself in any serious way. George Newcomb and Charlie Pierce tumbled out of their saddles and were probably dead before they hit the ground. Newcomb was buried in Norman, Oklahoma, but his grave was later washed away.

Pierce was buried in Guthrie under a tombstone that read, Charlie Pierce, Desperado. Almost exactly four months later, it was the turn of long-time Dulin associate William Little Bill Radidler. He's one of the lesser-known members of the gang, but he had been a cowboy with Bill Dulin before they all committed themselves to the lives of outlaws. Bill Raidler had eluded one of the famed three guardsmen of the Deputy U.S. Marshals, Chris Madsen, but he would not elude a second.

Deputy Marshal Bill Tillman was on Raidler's trail, and Tillman and two other lawmen caught Raidler on September 6, 1895. When Tillman ordered Raidler to surrender, Raidler refused. Like all members of the gang, he was quick to fight. Raidler started shooting his rifle, but a bullet fired from one of the lawmen smashed into the outlaw's wrist and forced him to drop his gun. Unable to shoot, Radler ran. Another round hit him in the back of the neck and dropped him to the ground. Remarkably, when Deputy Tillman walked up to the outlaw, he saw Radler was still alive. Tillman took Radler into custody and the wounded criminal beat the odds. He survived his injury and stood trial for charges related to the Dover train robbery. Raidler was found guilty and

sentenced to 10 years in prison. He served eight and was paroled in 1903. He passed away in 1909 or 1910, which made him one of only two members of the gang who lived that long. The other was Roy Doherty, who had been captured at the Battle of Ingalls. Meanwhile, the Marshals were still at work, and the next outlaw to stumble into their net was Bill Doolin. Bill Doolin had not yet faced the marshals of Oklahoma territory because he had fled Oklahoma territory. He lived in New Mexico territory during the summer of 1895, and if he had stayed there, he may have lived longer. Instead, he and his wife moved to southeastern

Kansas, which was far too close to the lawmen who were hunting for him in Oklahoma. Doolin went to Eureka Springs, Arkansas in January 1896. He hoped the soothing waters in the town's bathhouses would help his wounded and fatigued body. Maybe they did, but he unknowingly delivered himself into the hands of Deputy U.S. Marshal Bill Tillman. On January 15th, Tillman surprised Doolin, and Doolin didn't put up a fight. The leader of the most infamous outlaw gang of the time was in federal custody. But that didn't mean his story was over, far from it, and two of his associates would join him

in the newspaper headlines. Dan Clifton, nicknamed Dynamite Dick, was also captured by the U.S. Marshals. Doolan and Clifton were sent to Guthrie, Oklahoma, where they would stand trial. When Doolan arrived in town, hundreds of people assembled to see the man whom some called the King of the Outlaws. But if he were the King, he was rapidly losing his band of merry men. Bill Dalton, Bill Blake, George Newcomb, and Charlie Pierce were dead. William Radler was in prison, and at that moment so were Dulin and Clifton. Next to fall was George Red Buck Waitman. While Dulin and Clifton sat in jail in Guthrie, Waitman was killed on March 4, 1896, while resisting a posse in Custer County, Oklahoma. Almost exactly four months later,

Doolin and Clifton decided they were done with jail. On July 5, 1896, Doolin initiated an escape. With the help of other prisoners, including his friend Dan Clifton, Doolin jumped the jail's night guard. A second guard witnessed the attack and tried to run, but Doolin caught him and disarmed him. Doolin pointed the gun at the guard's chest and ordered him to open all the cells. The guard complied, and 14 prisoners escaped that night. They grabbed coats, hats, vests, and weapons and made their

way out of the Guthrie jail. Outside of Guthrie, Doolin and Clifton held up a buggy. They threw a man and woman out of the carriage and took off. Doolin and Clifton then parted ways. Bill Doolin reunited with his wife, and they hid in Lawson, Oklahoma. Doolin enjoyed just two months of freedom before one of the three guardsmen came calling. Deputy U.S. Marshal Heck Thomas led a posse that included the Dunn brothers, who had killed George Newcomb and Charlie Pierce. After weeks of tracking, Thomas and his posse met a blacksmith who reported Doolin's location near Lawson. The posse finally closed in on the King on August 25, 1896. As with the Battle of Ingalls, there are some wild discrepancies about the confrontation.

Some accounts claim Heck Thomas found Bill Dulin on the farm where Dulin was hiding. Other accounts say Dulin was walking through the town of Lawson when the posse spotted him. Ultimately, Doolin was outside and in the open when Deputy Thomas identified himself and shouted for Doolin to stop moving. Doolin paused for a moment and Thomas told him to surrender. Doolin scanned the area and saw he was outnumbered. He had no interest in surrendering and had no desire to face a prison cell again. A tense moment passed and then Bill Doolin opened fire. He carried a Winchester rifle and a pistol and he tried to use both to fight the posse.

The posse returned fire and there was no hope for Bill Doolin. No one knows for sure who killed Doolin that day, but the fatal shots were from the barrels of a shotgun, possibly fired by Heck Thomas. Doolin took the buckshot to the chest, and the blast knocked the outlaw to the ground. When it was clear Doolin was dead, the posse loaded him onto a wagon to transport him back to Guthrie. In Guthrie, Doolin's body was displayed and photographed. The picture shows a shirtless Bill Doolin, bony and thin with a scruffy beard and mustache

and at least 20 wounds on his chest. Four days later, he was buried in the Summit View Cemetery in Guthrie, where his burial plot remains today. Bill Doolin's widow sued the Marshals Service for wrongful death, but the case was dismissed the following year. By the end of August, 1896, just two members of the Doolin-Dalton gang

remained alive and free, Dan Clifton and Richard West, and they were on borrowed time. Twenty months, to be exact. Clifton was a minor criminal before Bill Doolin welcomed him into the fold. Now, Clifton was wanted for a slew of crimes and he was an escaped fugitive. He successfully laid low for a few months after his jailbreak with Bill Doolin and the U.S. Marshals lost track of him. But they found his trail at the end of the year, and Deputy Chris Madsen led a posse

in pursuit. On December 4, 1896, the posse found the outlaw at a farm in Newkirk, a settlement in eastern Oklahoma. Clifton refused to surrender, and according to a local newspaper, he put up a tenacious fight. More than 100 rounds were fired as he took on an entire posse. For a while, he seemed to hold his own. But Clifton's luck ran out when he tried to escape, and the posse shot him as he made his break. No one claimed Dan Clifton's body, and he was buried in an unmarked grave at Green Hill Cemetery in Muskogee, Oklahoma. And then there was

one, Richard West, probably the least known of the gang members. West was a cowboy who was believed to have been born in Texas. He stood just 5 feet 1 inch tall, but he was not afraid to fight. He participated in most of the major heists the gang committed, and he was wounded during the bank robbery in southwest city, Missouri. After the gang broke up, West joined brothers Al and Frank Jennings to form the Jennings Gang. The five-man gang was a miserable failure, and they never managed a successful robbery. In 1897, four of the five were captured, and only Richard West remained free. He stayed free for another year, until he made the extremely unwise decision to go to Guthrie, the territorial capital of Oklahoma. In April 1898, West was confronted by a group of lawmen. In most stories, Deputy Marshal

Chris Madsen led the group, but in others, it was led by the other two guardsmen, Heck Thomas and Bill Tillman. Either way, like most of West's friends in the Doolan-Dalton gang, he refused to go quietly. West shot it out with the lawmen, and predictably, he lost. Richard West, the last surviving outlaw of the original Wild Bunch, died on a street in Guthrie. He was buried near his friend, Bill Doolin, at Summit View Cemetery northeast of town. From the gang's first robbery, led by Bill Doolin in the small town of Spearville, Kansas in November 1892, to the final shootout in Guthrie, Oklahoma in April 1898, various members of the Doolin-Dalton gang were alive and active for five and a half years. Like most outlaw gangs, they packed a lot of adventure and destruction into a relatively

short space of time. Then, one year after West was killed, Butch Cassidy and the Sundance Kid committed their famous train robbery near Wilcox, Wyoming. It was the final major heist of their careers and the end of the era for the major outlaws of the Old West. They were all immortalized by dime novels, and as the years rolled by, new forms of media emerged. The first big movie about the Doolin-Dalton gang was released in 1949, 53 years after

Bill Doolin's death. It was called The Doolins of Oklahoma, and it starred early Western movie icon Randolph Scott as Bill Doolin. In April, 1973, 75 years after Richard West's death, the American rock band The Eagles released their Western-themed concept album, Desperado. Three songs pay homage to the Doolins and the Daltons. Duelin

Dalton, obviously, Bitter Creek, which was loosely inspired by George Bitter Creek Newcomb, and 21, which was about Emmett Dalton, who was 21 years old when he survived the Coffeeville raid. Next time on Legends of the Old West, it's a topic that has been requested often, the Transcontinental Railroad. As a singular topic, it's enormous, so we're going to tell some exciting individual stories that represent different aspects of the grandest construction project in the American West, maybe in all of American history. Those stories start next time on Legends of the Old West.

Members of our Black Barrel Plus program don't have to wait week to week to receive new episodes. They receive the entire season to binge all at once with no commercials. And they also receive exclusive bonus episodes. Sign up now through the link in the show notes or on our website blackbarrelmedia.com Memberships are just five dollars per month. This series was researched and written by Michael Meglish. The producer was Joe Guerra. Original music by Rob Valier. I'm Chris Wimmer. Thanks for listening.