Image: William “Bill” Doolin (Public Domain)

William Doolin was an American outlaw and founder of the Wild Bunch, sometimes called the Doolin- Dalton Gang. Like the earlier Dalton Gang alone, it concentrated on robbing banks, trains, and stagecoaches in Oklahoma, Kansas, Arkansas, and Indiana, during the 1890s.

Bill Doolin was born in 1858 in Johnson County, Arkansas, to Michael and Artemina Doolin. Bill Doolin became a cowboy in Indian Territory in 1881, where he worked for cattleman Oscar Halsell. During this period, Doolin worked with other cowboy and outlaw figures prevalent at the time, including Dan “Dynamite Dick” Clifton, George Newcomb (known as “Bitter Creek”), Dick Broadwell, Charley Pierce, Bill Power, Bill “Tulsa Jack” Blake, and the more well-known Emmett Dalton.

Doolin’s first run-in with the law happened on July 4, 1891, in Coffeyville, Kansas. Doolin and many other cowboys were drinking beer and having a good time. Two lawmen appeared and asked who owned the beer, “Nobody owns it,” replied Doolin, who was in charge of the party, “It’s free. Help yourselves.” One of the lawmen then announced, “It’s against the law to drink beer in this state, and we are going to pour the beer out.” Doolin indignantly replied, “If you pour our beer out, you’re going to get hurt.”

The officers determinedly began to push one of the barrels over, and several cowboys drew their weapons. A wild shootout followed, and the two lawmen were killed. No one was sure who fired the fatal shots, but Doolin feared he would be blamed, so he decided to flee. He would soon join the Dalton gang.

On July 15, 1892, Doolin and the rest of the Dalton gang rode into Adair, Oklahoma, planning to rob the 9:42 evening train. About fifteen minutes before the train was due to arrive, the outlaws broke into the train depot and grabbed all the available money. When the train arrived, they jumped aboard the cab, backed a wagon up to the express car, and intimidated the messenger until he wisely opened the door. Three outlaws jumped inside, forced the messenger to unlock the safe, and took all its contents.

In the meantime, guards opened fire from the smoker, but several of the gang riddled the car with bullets and wounded three of the lawmen. Two bystanders were struck, one fatally. Finally, the money was placed into the wagon, and the gang took off victoriously out of town.

On October 5, 1892, the Dalton gang tried to hold up two banks at the same time in Coffeyville. It was a terrible failure. Coffeyville lawmen and citizens rallied in a shootout against the outlaws, killing four of the five gang members. Emmett Dalton was arrested and convicted at trial, and imprisoned. There has been speculation that a sixth gang member was in town, minding the horses in an alley, and managed to escape. The sixth man has never been identified. Some speculate that it may have been Bill Doolin.

In late 1892, Doolin created his own gang known as the Wild Bunch. On November 1, 1892, they robbed a bank in Spearville, Kansas. After the robbery, the gang bolted with crewmember Oliver Yantis to Oklahoma, where they hid out at the home of Yantis’s sister. A month later, the crew was traced to that house. In a shootout, Yantis was killed, but the remainder of the outfit escaped.

Two teenage girls, known as Little Britches and Cattle Annie, also followed the gang as outlaws. They alerted the men whenever lawmen got too close. Some historians maintain that Doolin gave bandit Jennie Stevens her nickname of Little Britches.

Following the Spearville robbery, the gang went on a spree of profitable train and bank robberies. In March 1893, Bill Doolin married Edith Ellsworth in Ingalls, Oklahoma.

On May 30, 1893, Doolin masterminded a train robbery at Cimarron River near Ashland, Kansas. When he and three band members crossed the Cimarron River to return to Oklahoma, they were intercepted by a posse led by lawman Chris Madsen. The outlaws and the posse began trading gunfire, and Madsen shattered Doolin’s right foot with a steel-jacketed rifle bullet. Doolin then led his men as they rode safely away from the surprise attack. He retreated to meet up with his wife and seek medical attention.

On September 1, 1893, Doolin and his gang rode into Ingalls, Oklahoma, a regular place for them to rest. Doolin, Bill, Dalton, Bitter Creek Newcomb, Tulsa Jack Blake, Red Buck Weightman, and Dan Clifton all went to the Ransom and Murray Saloon while injured Arkansas Tom Jones went to a room in the City Hotel to lay in bed. However, the authorities had been warned that the gang would be there, and numerous lawmen closed in on the town and soon began the Battle of Ingalls.

The outlaws began playing poker in the saloon, but Newcomb soon stepped out on the veranda to check the street. Lawman Dick Speed took a shot at him, and the gunfight started. Despite being wounded, Newcomb managed to find his horse and ride out of town while Arkansas Tom and the outlaws in the saloon began exchanging shots with the officers. Speed was shot dead in the street, a boy named Dell Simmons was killed, and a bullet struck another bystander in the chest.

There was a brief pause in the fight, and the lawmen began to move in, calling on the outlaws to surrender. Doolin defiantly shouted, “Go to hell!” and the fighting resumed with renewed vigor. As the posse rained vast amounts of lead into the building, saloon owners Ransom and Murray were hit in the leg and the side and arm, respectively. Doolin slipped out to the nearby livery stable, then provided covering fire while his compatriots joined him.

Doolin and Dan Clifton quickly bridled their horses and rode out the rear door toward a draw while Dalton, Blake, and Weightman galloped through the front entrance. After vicious shooting on the street, the last three outlaws turned their horses around and tried to follow Doolin and Clifton. A wire fence blocked their path, but Dalton went to work with a pair of wire cutters. Lawman Lafe Shadley advanced, but Dalton killed him and returned to his job. When the fence was cut, Doolin rode back, pulled Dalton up behind him, and the outlaws rode off to safety.

During the gunfight, three marshals and two bystanders were killed, one bystander was wounded, three gang members were injured, and gang member “Arkansas” Tom Jones was injured and subsequently arrested. Doolin killed Deputy Marshal Richard Speed during the melee.

For a while, the Wild Bunch was the most dominant outlaw group in the Old West. Because of the unrelenting pursuit by the marshals known as the Three Guardsmen (lawmen Heck Thomas, Bill Tilghman, and Chris Madsen), by the end of 1894, they had either captured or killed several members of the gang. By late 1894, gang member Bill Dalton had been killed by U.S. Marshals. Rewards were offered for the arrest or killing of remaining gang members, a device that often turned friends into foes to collect the reward money. On May 1, 1895, gang members Charlie Pierce and George “Bittercreek” Newcomb were killed by two bounty hunters, the Dunn brothers. They were the older brothers of Rose Dunn, the teenage girlfriend of Newcomb. She had betrayed Newcomb, but her brothers may have followed her to the outlaw’s hideout.

On May 20, 1895, Doolin led his gang into Southwest City, Missouri, intending to hold up the local bank. Doolin and several henchmen went inside and declared their intentions. But while the robbery occurred, former State Attorney J.C. Seaborn attempted to pull a weapon. The outlaws killed him, and before the gang could get out of town, there was a vigorous exchange of gunfire. Doolin was wounded in the head but stayed in the saddle, and the crew escaped to safety.

In the Spring of 1895, near Dover, Oklahoma, Tulsa Jack Blake was guarding the sleeping gang’s camp on the Cimarron River. Suddenly, a posse drew near, and a gunfight began. Blake was killed, but Doolin and the rest of the gang dashed to safety.

Doolin escaped to New Mexico Territory, where he hid out with outlaw Richard “Little Dick” West during the summer of 1895. Late that year, Doolin and his wife went to Burden, Kansas. They crossed the border to visit the resort in Eureka Springs in northern Arkansas. There, Doolin soaked in the sulfur springs in the bathhouses; the waters relieved rheumatism in his foot that set in after a previous gunshot wound. In January 1896, lawmen Bill Tilghman single-handedly captured Doolin at Eureka Springs, Arkansas. The outlaw, who was at the springs to take in the medicinal waters, was caught by surprise, and Tilghman arrested him peacefully. He was jailed at Guthrie, Oklahoma, to await trial.

Doolin broke out of jail on July 5 and headed for Lawson, Oklahoma. Doolin began hiding at the New Mexico ranch of writer Eugene Manlove Rhodes. In August, he was resolved to bring his wife and son to New Mexico, and he returned to the farm of his father-in-law, a minister, located just outside Lawson. Carrying a Winchester and leading his horse, Doolin was walking down a lane near the house in the bright moonlight.

However, U.S. Deputy Marshal Heck Thomas had been notified of Doolin’s whereabouts, and there were lawmen on both sides of the road. Thomas ordered Doolin to surrender, but the outlaw immediately began firing. A bullet from the posse knocked the Winchester from his hands, but Doolin took out his pistol and fired off a round or two before Thomas, firing a rifle, and posse member Bill Dunn, armed with a shotgun, killed him by blasting twenty-one holes in his body. He was 38 years old.

Image: Bill Doolin’s passing was as violent as the rest of his Wild Bunch. As with him, all their deaths were by gunshot. (Public Domain)

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