Controversial Death of a Cop Killer


Situation: A police command is met with gunshots and the police return fire.

Lesson: Manhunts can take surprising turns and alternate histories of what happened can start as soon as the echoes of the gunfire die away.

In the Old West, it was common to photograph the bodies of men killed in gunfights and circulate the pictures. Any student of the time recalls the image of Billy Clanton and brothers Tom and Frank McLaury in their caskets in Tombstone. Ditto the photo of Bill Powers, Bob and Grat Dalton and Dick Broadwell lying dead after the Coffeyville, Kansas raid. In the Arizona photo, the dead men are wearing their funeral suits, and in the Kansas image, someone at least had the good taste to close the dead men’s eyes.

Not so another famous picture, this one from Oklahoma. The fresh corpse is stripped to the waist, and his dead eyes stare vacantly upward. Sprinkled across his chest and shoulders are the many round entry wounds that ended his life, four of which pierced his heart.

His name was Bill Doolin. Some called him the last of the most infamous Wild West outlaws. His death did not go unwitnessed, but there are many different stories about how it happened.

The Hunted

Doolin had been a member of the Dalton Gang, which famously came to grief when they were decimated by the armed citizens of Coffeyville while attempting to rob two banks at once and killing several innocent people. It was speculated, but never proven, that Doolin had been holding the gang’s spare horses at Coffeyville. He later joined up with another Dalton brother, Bill Dalton, forming the Dalton-Doolin Gang. Doolin’s followers later morphed into what became known variously as The Wild Bunch (not to be confused with Butch Cassidy’s group) and the Oklahombres. Doolin was involved in many robberies and some shootings in which law enforcement officers were shot; those bullets may or may not have come from Doolin’s guns. However, he took a major part in a hellacious gunfight in Ingalls, Okla., which became known as The Battle of Ingalls, and there, Doolin unquestionably murdered a 25-year-old deputy U.S. marshal named Richard Speed.

The Chief Hunters

If the FBI had existed then, Doolin would have been high on their Most Wanted List, perhaps even Public Enemy Number One. Every lawman in the Oklahoma Territory was looking for him, and more than one bounty hunter, because the price on his head was $5,000 — the equivalent at the time of more than $188,000 today. But three of those manhunters stand out, a trio of deputy marshals expressly ordered by the United States Marshal Service to concentrate on Bill Doolin and to bring him in dead or alive. Their names were Chris Madsen, Bill Tilghman and Heck Thomas. They would famously become known as The Three Guardsmen.

Each of those men had an awesome back story and two had literally been child warriors on battlefields. Christen Madsen (1851—1944) was born in Denmark and was said to have begun as a 13-year-old messenger during a German/Danish military conflict before serving in the Danish Army, the French Foreign Legion, and finally the United States Army before entering law enforcement. He would later title his memoirs Under Three Flags.
Bill Tilghman (1854—1924) hunted buffalo as a young man, much as Wyatt Earp and Bat Masterson did. Tilghman estimated he killed 3,300 bison during that period. He later served as a deputy under Masterson before becoming a deputy U.S. Marshal.

Henry “Heck” Thomas (1850—1912) was taken to the Civil War by his father, a Confederate officer from Georgia, and was a messenger on a Virginia battlefield at age 12. He had been a railroad detective before being appointed Deputy U.S. Marshal.

Each of the Three Guardsmen would separately have a profound impact on Bill Doolin. One would cripple him for life, another would personally arrest him, and the third would finally end him.

Madsen Shoots Doolin

The time came when Madsen made direct contact with Doolin — in the ballistic sense. Historian Tom Clavin recounts the incident as follows in his eminently readable 2023 book The Last Outlaws: The Desperate Final Days of the Dalton Gang:

“… Santa Fe Railroad’s California Express just west of Cimarron, Kansas (was robbed) in June. The messenger, a man named Whittlesey, had been wounded when the gang fired into the express car to persuade him to open it. After grabbing about $1,000, Doolin set up a cot and laid the wounded messenger on it, then he jumped on his horse and dashed off with the others. In Guthrie, Deputy Marshal Chris Madsen was assigned to pull together a posse and catch up to the bandits.

“He and his ‘deputies’ — who were actually Indian scouts — almost did. By figuring out where the bandits were going to enter Oklahoma and some hard riding, the posse was able to intercept Doolin and his fleeing comrades. Shots were exchanged and a bullet fired by Madsen from a new .30-30 Winchester found Bill Doolin’s right foot. He would later learn the steel-jacketed bullet entered his heel and traveled to the ball of the foot, where it shattered the bone. For the rest of his days, Doolin would be in pain.”

Looking at it as a shooter, Madsen must have been a very early adopter of the .30-30 Winchester since the above incident supposedly took place in 1893, and the .30-30 wasn’t introduced officially until 1895, a year after its home rifle the Winchester Model 1894 debuted in calibers such as .38-55. One wonders if author Clavin might have been misinformed. Steel-jacketed bullets for .30-30 don’t sound right either. No matter: Whatever Madsen shot him with, Doolin’s foot was mangled, and he would be crippled thereafter, in constant pain, always limping and often walking with a cane. In fact, that injured foot would take him to the place where he would next run afoul of The Guardsmen.

Tilghman Arrests Doolin

Bill Tilghman was a highly skilled investigator. In January 1896, the deputy marshal received a tip that Doolin and his wife and baby son were in Eureka Springs, Ark., in hopes that the hot mineral springs there might ease the agony of his crippled foot. Tilghman, posing as a preacher, spotted Doolin before Doolin could notice him. He found him in the waiting room of a bathhouse. Clavin picks up the story from there:

“With his six-shooter in hand, the deputy emerged and strode across the waiting room. When he got to Doolin, he ordered the bandit to surrender. ‘What do you mean?’ Doolin responded, standing. ‘I have done nothing.’

“Still, his right hand went for his gun, and Tilghman grabbed his wrist. Then, pointing his pistol at Doolin’s face, he again ordered him to surrender. Meanwhile, the gentlemen’s waiting room emptied out fast. ‘Bill, don’t make me kill you,’ Tilghman implored.”

The pragmatic Doolin surrendered. Clavin continues, “With help from the bathhouse owner, Tilghman completely disarmed Doolin. It was as he was shackling him that Doolin, peering closely, said, ‘You’re Tilghman.’” The deputy telegraphed to headquarters, “I have him. Will be home tomorrow. Tilghman.” Doolin offered no further resistance, and the train was met at Guthrie, Okla., by a throng of curious citizens. “There was a great pushing, scrambling, and crowding for a glimpse of the ‘King of Outlaws,’” Tilghman himself wrote later.

Heck Closes The Case

After initially agreeing to a plea bargain in which he would serve 50 years for the killing of Deputy Marshal Speed, the clever Doolin promptly managed to escape. The manhunt was on again.

It finally ended on August 24, 1896. Heck Thomas had gotten word that Doolin regularly visited his wife at her father’s place in Lawson, Oklahoma Territory. Thomas and a small posse staked the place out.

In the wee morning hours of darkness, they see a tall man (Doolin was 6’2″) leave the building carrying a rifle. Thomas shouts out a challenge. Doolin instantly responds with a shot from his Winchester and a ripple of gunfire answers from the posse. Their return fire strikes the rifle, rendering it useless; Doolin drops it, draws his Colt, and fires. More gun thunder erupts from the posse, and Doolin falls.

It is over in a very few seconds. Bill Doolin falls to the ground, killed almost instantly. The echoes of the shooting fade away into a moment of silence as the long-hunted killer passes into history.

Only one question remains, and forever after: Who actually killed Bill Doolin?

Different Theories Arise

Let’s hear from the man himself. In Dee Cordry’s article “The Last Days of Bill Doolin” in the Oklahombres Journal, we find excerpts of Heck Thomas’ letter to Bill Tilghman. A few days after the shooting. Tilghman wrote:

“We waited a long time without seeing anyone … Finally [Doolin] came out of the stable and to our great surprise, started down the lane coming west, you know how the store is situated on the high prairie … If Bill had wanted to have made his escape he could have had open roads north, south, east, northeast, or … northwest through the pasture to those high hills that you have seen many times. Well, he came right down the lane leading his horse by the tip ends of the bridle reins, walking slow in the bright moonlight, Winchester in both hands, well out in front of him, nearly in position to shoot. He sure was on the prowl … looking first to one side and then the other … Then I hollowed (sic) to him and had one of the other boys on the other side of the road hollow to him … He shot at me and the bullet passed between me and B. Dunn. I had let one of the boys have my Winchester and had an old No. 8 shotgun. It was too long in the breech and I couldn’t handle it quick so he got another shot with his Winchester and as he dropped his Winchester from (a) glancing shot, he jerked his pistol and some of the boys thought he shot once and the others twice — and about that time I got the shotgun to work and the fight was over.”

The conventional wisdom has always had it that Heck Thomas fired the shotgun blast that killed Bill Doolin. However, other theories emerged over the years. Some said posse member William “Bee” Dunn fired the fatal shot(s). Dunn and his brother were bounty hunters who had killed two other members of the gang on another occasion.

Many historians simply ascribe the death to “the posse,” since after all the whole group returned a hail of gunfire after Doolin triggered the first shot from his Winchester, a fact that does not seem to be in serious dispute.

However, after the famous photo of Doolin’s unclothed, riddled torso was circulated, another theory emerged. Noting that the body appeared to be emaciated, that theory held that Doolin had died naturally of tuberculosis, the posse had somehow gained possession of the corpse, and they had riddled it with bullets so they could claim the reward. The theory was based on the absence of blood on the body in the photograph. What the theorists missed was that other witnesses stated that the hay on the bed of the wagon that brought Doolin’s body back to town was saturated with his blood and that the photo in question had been taken after the blood had been cleaned from Doolin’s corpse.

A variation of that theory emerged in modern times from one Doug Doolin, who claimed to be a distant relative of the dead outlaw. He said that according to family history, a generous and compassionate Heck Thomas found Doolin dead of tuberculosis and shot the corpse so he could claim the reward money and give it to Doolin’s widow.

That last would make a great heart-tugging story for Reader’s Digest, but there is no evidence to support it. According to Tom Clavin, the offered $5,000 reward was never paid. Clavin elaborates, “Heck Thomas was well compensated for finding and finishing off the remaining leader of the Doolin-Dalton Gang. The Wells Fargo Company gave him $500, and the same amount was soon paid by the state of Missouri, and the railroads came up with an additional $300. Of this $1,300 total, Heck kept $400 and doled out the rest to the members of his posse and to Tilghman, who had not received any reward for tracking Doolin down the first time because it required ‘arrest and conviction.’”

Even if the reward money to the widow thing didn’t happen, there were other elements of human compassion in the story.


Don’t take an unfamiliar weapon to a gunfight. What the heck was Heck Thomas’s fumbling with the shotgun all about? That “No. 8 shotgun” was an eight gauge, a humongous weapon that was, by his own admission, too clumsy for him to handle quickly. For perspective, a modern 12-gauge shotgun shell most commonly fires an ounce of shot, nine 00 buck pellets; a 10-gauge Magnum launches two ounces (18 double aughts); and the black powder eight gauge of the day held even more, which could account for every one of the 20 or so holes in Bill Doolin’s torso. Thomas described a bullet going past him and lost precious time fumbling with the huge shotgun. Did he decide to use it in lieu of his own Winchester rifle because he thought the massive swarm of buckshot would be helpful in the dark? We simply do not know. We do know that while he was messing with it, based on eyewitness accounts, a known cop-killer fired somewhere between one rifle shot and one revolver shot, to two from the Winchester and as many as three from his revolver before he went down. (Gun nerd factoid: Doolin’s rifle was caliber .40-82, which would make it a Model 1886 Winchester, and coincidentally Thomas had reportedly brought an identical rifle in the same caliber that night. The black powder .40-82 load comprised a 0.408″ 260-grain bullet at 1,350 feet per second.)

Beware of misplaced compassion. In the arrest of the known cop-killer Doolin in the bathhouse, the desperate 6’2″ fugitive might have overpowered Tilghman’s grasp of his wrist and gotten his own revolver into action. Tilghman would have been justified in firing a .45 Colt bullet through Doolin’s brain as soon as the man grasped his own gun. In 1924, a then 62-year-old Bill Tilghman was murdered by a rogue liquor agent he was arresting and had disarmed of one gun when the man pulled a second and mortally wounded him. Perhaps Tilghman had dropped his guard because he thought another lawman, however violent, was one of his own. It was an example of Ayoob’s Law #5: “Professional courtesy only works between courteous professionals.”

BS lawsuits against law enforcement for justified shootings are nothing new. Bill Doolin’s widow, Edith, sold pictures of her dead husband for 25 cents apiece and also filed a wrongful death suit over the killing of her husband, who had been shot after opening fire on police. The lawsuit was dismissed the following year. Another interesting factoid: After the Battle of Ingalls, in which a bartender had taken the side of the outlaws, opened fire at the marshals, and got shot up for his pains, the bartender, too, filed a lawsuit. That one was also thrown out of court.

Santayana was right when he said those who ignore history are doomed to repeat it. The dynamics of human violence remain largely the same across the ages. All that changes are the clothing, the hardware and the vehicles that brought the humans to the given mortal conflict.

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