- Frank R. Prassel
Doolin, William (1858–25 August 1896), cowboy and bank and train robber, was born in Johnson County, Arkansas, the son of Michael Doolin and Artemina Beller, farmers. Bill Doolin had a normal childhood and remained on the family farm until 1881. He was a tall, slender man, lacking a formal education and barely literate but generally regarded as intelligent and personable. At twenty-three, Doolin left home to seek his fortune on the closing frontier. He quickly became a proficient cowboy for Oscar Halsell and other ranchers operating near the Cimarron and Arkansas rivers of the Oklahoma Territory. For several years Doolin worked his way across the western ranges of Wyoming, Montana, California, Arizona, and New Mexico, earning the reputation of a reliable, capable, and good-natured hand. He was considered to be a fine rider, an excellent shot, and a natural leader when he returned to the cattle ranches of Oklahoma.
Doolin and several other cowboys visited nearby Coffeyville, Kansas, for the Fourth of July celebration in 1891 and perhaps inadvertently launched a prominent career in crime. When local constables attempted to confiscate the visitors’ illegal beer, a gunfight erupted, and the lawmen were shot. Probably already bored with ranch life, Doolin joined the notorious Dalton gang of train robbers. For thirty-three years the former cowboy had lived an ordinary life, giving no indication of a proclivity for criminal behavior, but within months Doolin would be widely known as a desperate, dangerous fugitive, and “King of the Oklahoma Outlaws.”
Doolin soon participated in several Dalton depredations in the Indian Territory, but although he was credited with at least six killings, he remained only a peripheral member of the outlaw band. On 5 October 1892 the Daltons attempted to rob two banks simultaneously in Coffeyville, Kansas. The raid proved disastrous, with four members of the gang killed by townsmen. Doolin either escaped or was not involved in the fighting. Instead, he quickly emerged as the new leader of a reorganized and even more formidable outlaw organization. Doolin’s gang struck repeatedly at trains and banks in Kansas, Missouri, and the Oklahoma Territory. About twenty individuals participated in these offenses, but typically only three to five members were involved in any specific act. The robberies were marked by careful planning, rapid execution, violence when necessary, and skillful escape.
The leader of these versatile and active criminals found time for a family. In 1893 Doolin married nineteen-year-old Edith Ellsworth, daughter of a Methodist minister. The couple had one son, Jay. Doolin and his criminal colleagues enjoyed good relations with many settlers, furnishing them with provisions and money in return for information and warnings of any efforts at apprehension. Helpful spies for the gang included two young women, Annie McDoulet and Jennie Stevens, popularly known as “Cattle Annie” and “Little Breeches.”
Doolin’s robbers usually operated from Ingalls, a small community in the Oklahoma Territory about ten miles east of Stillwater. Deputy federal marshals learned of this center for crime, realized the futility of direct attack, and decided to infiltrate the settlement by masquerading as homesteaders hiding in covered wagons. On 1 September 1893 the plan reached its climax with the “Battle of Ingalls,” one of the bloodiest confrontations between outlaws and lawmen on the frontier. Doolin and most of the gang escaped, leaving four members of the posse and one innocent citizen killed or fatally wounded in the five-hour gunfight. The raid on Ingalls was a disastrous effort to apprehend the outlaws, but it led to the gradual disintegration of their organization.
A massive manhunt involving federal marshals, private detectives, and local peace officers began. The reward offered for Bill Doolin reached $5,000 “dead or alive,” despite which he continued to direct robberies for two years. Public support for the outlaws eroded, however, and such members of the gang as “Arkansas Tom” (Ray Daugherty), Bill Dalton, “Tulsa Jack” Blake, Charley Pierce, and George “Bitter Creek” Newcomb were killed. By 1895 the surviving outlaws had scattered. Doolin sought refuge under an assumed name on the ranch of Eugene Manlove Rhodes in the mountains of eastern New Mexico. The fugitive also attempted, without success, to negotiate a surrender in return for a reduced charge and sentence.
Suffering from rheumatism, Doolin finally sought relief at the bathing resort of Eureka Springs, Arkansas. Deputy federal marshal Bill Tilghman diligently followed the trail and on 15 January 1896 arrested him in the Davey Hotel. News of the apprehension attracted a multitude of spectators to Guthrie, Oklahoma Territory, where Tilghman had taken his prisoner. Doolin was taken on a tour of the town, during which he shook hands with hundreds of fascinated citizens.
Confined for the first time in his life, the notorious outlaw declined the offer of a fifty-year sentence in return for a plea of guilty to the killings at Ingalls. On the night of 5 July 1896, still awaiting trial, he joined thirteen other prisoners and broke out of the federal jail at Guthrie. The escapees quickly scattered; most were never recaptured.
Doolin hid on the Cimarron River near his wife and son, who were then living in Lawson (later Quay), a small community some ten miles east of Ingalls. A local informant furnished information on the fugitive’s movements, and Deputy Federal Marshal Heck Thomas planned an ambush. Just after sundown on 24 August 1896 Doolin said goodbye to his wife and walked down a road, where the posse was waiting. A fusillade of shots brought an immediate end to the outlaw’s life. He had never been convicted of any crime.
Bill Doolin was quietly buried at Guthrie three days later. For decades only a rusting buggy axle marked the grave. Marshal Thomas eventually collected only $1,435 of the promised reward, a sum that did not cover his expenses.
Leading sources include Bailey C. Hanes, Bill Doolin: Outlaw O. T. (1968); Glenn Shirley, West of Hell’s Fringe (1978); and Paul Wellman, A Dynasty of Western Outlaws (1961).