Bill Doolin – Leading the Oklahombres


Bill Doolin

Bill Doolin

William M. “Bill” Doolin, aka Will Barry (1858-1896) – More than 100 years ago in a quiet little town in the Oklahoma Territory, members of the infamous Oklahombres gang squared off against a posse of deputies in one of the deadliest confrontations in the history of the U.S. marshals. By the end of the gunfight, nine men lay dead or wounded, and the people of Ingalls had a vivid picture of Western lawlessness and the harsh means needed to restore justice.

William “Bill” M. Doolin was born in 1858 in Johnson County, Arkansas to Michael Doolin and Artemina Beller Doolin.  At the age of 23, he drifted west, working at odd jobs until he landed a job as a cowboy at the H-X Bar Ranch on the Cimarron River in Indian Territory in 1881. The ranch was owned by a Texan named Oscar D. Halsell, who took a liking to Doolin, teaching him to write and do simple arithmetic, and eventually, making him an informal foreman on the ranch.

For the next decade, he continued to work as a cowboy at several area ranches and was considered trustworthy and capable. It was during these years that Doolin worked with other cowboy and outlaw names of the day, including George “Bitter Creek” Newcomb, Charley Pierce, Bill Power, Dick Broadwell, Bill “Tulsa Jack” Blake, Dan “Dynamite Dick” Clifton, and Emmett Dalton.

By the 1890s however, Doolin had hooked up with the Dalton Gang, participating in several train and bank robberies. His first encounter with the law occurred in 1891 in Coffeyville, Kansas when he and several friends were celebrating the 4th of July by tapping a keg of beer. However, at that time, Kansas was a dry state and when lawmen attempted to confiscate their alcohol, a shootout erupted, resulting in two lawmen being wounded. Doolin and his cohorts quickly fled the area. Doolin was then a wanted man and began his outlaw career earnest.

On October 5, 1892, the Dalton Gang made its fateful attempt to rob two banks in Coffeyville, Kansas. In the end, it was a total failure with Bob and Grat Dalton, Bill Power and Dick Broadwell being killed. Only Emmett Dalton survived to spend years in prison for the attempt. On the face of it, Doolin didn’t participate in this robbery, which spared his life, at least for a little while. However, since that fateful day, some historians have alleged that there was a sixth gang member in an alley holding the horses, who escaped. Though who that sixth man was remains a mystery, many speculate that it very well might have been Bill Doolin.

Soon afterward, Doolin founded another gang, the Oklahombres, who were also called the Wild Bunch and the Oklahoma Long Riders because of the long dusters that they wore.

This group specialized in robbing banks, stores, stagecoaches and trains in Arkansas, Kansas, Missouri, and Oklahoma, quickly becoming the terror of the Wild West. The gang included at various times Bill DaltonGeorge “Red Buck” Waightman, Little Bill Raidler, Bob Grounds, Bill “Tulsa Jack” Blake, Richard “Little Dick West”, Dan “Dynamite Dick” Clifton, Roy Daugherty, better known as “Arkansas Tom” Jones, Alf Sohn, George “Bitter Creek” Newcomb, Charley Pierce, and Oliver “Ol” Yantis. Two teenaged girls, known as Little Britches and Cattle Annie, also followed the gang.

Wasting no time, Doolin and his new gang robbed the Ford County Bank at Spearville, Kansas on November 1, 1892, getting away with cash and over $1,500 in treasury notes. Within no time, a notice was circulated of the robbers’ descriptions. The city marshal in Stillwater, Oklahoma recognized the description of Oliver “Ol” Yantis and a posse was sent looking for him. He would be the first of the gang to die when he was killed in a shootout on November 29, 1892 at Orlando, Oklahoma Territory.

On March 14, 1893, Doolin married Edith Ellsworth of Ingalls, Oklahoma in Kingfisher. Whether she knew that Bill was an outlaw is unknown, but she stood by him and the couple would have a son they named Jay.

On June 11, 1893, the gang was back on the trail again, robbing a train near Cimarron, Kansas. Making off with about $1,000 in silver, a posse was in quick pursuit, tracking them to a point north of Fort Supply, Oklahoma. When the guns began to blaze, Doolin was shot and wounded in the left foot. Though he was able to escape and recovered, he would walk with a limp for the rest of his life.

Ingalls, Oklahoma

Ingalls, Oklahoma

In August, 1893, several members of the outlaw gang, including Bill Doolin, Bill Dalton, George “Red Buck” Weightman, George “Bitter Creek” Newcomb, Charlie Pierce, “Arkansas Tom” Jones, “Tulsa Jack” Blake, and “Dynamite Dick” Clifton, were taking refuge in the small town of Ingalls, Oklahoma. Most of them had been in town for weeks living at the city hotel and spending their time at the Ransom Saloon.

When U.S. Marshals got word of their location, Marshal Evett Dumas “E.D.” Nix formed a posse of some 27 deputy marshals and Indian Police and headed towards Ingalls. Camping out along a creek the night before, they were seen by a young boy, who the deputies held overnight. However, the boy slipped away early the next morning and ran into Ingalls, telling the outlaws, “The marshals are coming.”

On September 1st, the posse entered the outlaw town of Ingalls with the intent to capture the gang. In what would be remembered as the Battle of Ingalls, three of the fourteen lawmen carrying Deputy U.S. Marshals’ commissions would die as a result of the battle. Two town citizens would also die; one killed while protecting the outlaws. Of the Doolin Gang, Newcomb was seriously wounded but escaped, and Arkansas Tom Jones, the killer of the three deputies and one citizen, was captured. He would be sent to prison, paroled in 1910, but after robbing another bank, he was killed on August 16, 1924, in Joplin, Missouri by police officers.

After the shootout, the gang laid low for a while but were back at it early the next year. On January 3, 1894, Charlie Pierce and George “Red Buck” Weightman held up the store and post office at Clarkson, Oklahoma. Just a few weeks later, on January 23rd, the gang robbed the Farmers Citizens Bank at Pawnee, Oklahoma, and March 10th the Oklahombres robbed the Santa Fe Railroad station at Woodward, Oklahoma of over $6,000.

Evett Dumas Nix

Evett Dumas Nix

Ten days later, on March 20th, Marshal Evett Nix directed his best deputies — the Three Guardsmen — Bill Tilghman, Chris Madsen, and Heck Thomas to take down the Wild Bunch, stating:

“I have selected you to do this work, placing explicit confidence in your abilities to cope with those desperadoes and bring them in — live if possible — dead if necessary.”

On April 1st gang members Bill Dalton and Bitter Creek Newcomb attempted to rob the store of retired US Deputy Marshal W.H. Carr at Sacred Heart, Oklahoma. The old lawman instantly recognized Bill Dalton and reached for his gun, at which point Newcomb drew his pistol and shot Carr in the wrist. However, the retired lawman wounded Newcomb in the shoulder. Dalton then shot Carr in the abdomen, but though wounded, Carr continued to shoot, chasing the fugitives outside, where they jumped on their horses and fled.

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