Bill Doolin spent the first half of the 1890s at the head of an outlaw band in Oklahoma Territory. Between the fall of 1892 and the spring of 1895 his men held up trains and banks across southern Kansas, the two territories that later became Oklahoma, and the edge of Missouri. On September 1, 1893, a federal posse found the band at Ingalls, a small town east of Stillwater, and three deputy United States marshals did not survive the day. Two people of the town died with them. Eight months later, in Southwest City, Missouri, a raid on a bank cost another man his life.
Doolin was never convicted of any of it. A deputy marshal arrested him at Eureka Springs, Arkansas, in January 1896, and a grand jury at Stillwater indicted him for murder in connection with the Ingalls deaths. He refused an offer of fifty years in exchange for a guilty plea and entered a plea of not guilty. He was also held at Guthrie to stand trial for bank and train robbery. Before any jury heard the case he escaped from the federal jail at Guthrie, on the night of July 5, 1896, and seven weeks later a posse led by a deputy marshal killed him near Lawson, in Payne County. The deaths at Ingalls produced one conviction, and it was not his.
Doolin was born in Arkansas in 1858, on a homestead near Big Piney Creek in Johnson County, about thirty-five miles northeast of Clarksville. He worked on the land in Arkansas until he was twenty-three.
In 1881 he left Arkansas for the country that would become Oklahoma. He found work as a cowboy on the ranch of Oscar D. Halsell near Logan, and for roughly a decade he drifted between ranches in Kansas and the Oklahoma country. The men he worked for regarded him as a steady, capable hand. Nothing in his early years marked him for the life he later took up.
The break came in the summer of 1891. Around July 4 of that year, near Coffeyville, Kansas, Doolin and other cowboys were holding a beer party in a state that had outlawed alcohol. Local officers moved to seize the beer, two of them fell in the confrontation that followed, and Doolin fled. Within months he had joined the gang led by the Dalton brothers.
From May 1891 to July 14, 1892, Doolin rode with the Daltons as they held up trains and railroad depots in the Oklahoma country. On October 5, 1892, the gang rode into Coffeyville to take two banks at once. Only one of the raiders, Emmett Dalton, came out of it alive. Doolin was not among them. His horse had gone lame on the way, and Coffeyville left him as the most experienced survivor of the old gang. He set about building a new one.
The band Doolin assembled in October 1892 drew on Dalton survivors and new recruits. Among the men around him in the next three years was Roy Daugherty, who used the name Tom Jones. Their targets were banks, trains and stagecoaches in southern Kansas, Oklahoma Territory and Indian Territory, and over about four years the takings were put at some $165,000.
The robberies came in a steady run. The first were a train at Caney on October 14, 1892, and the bank at Spearville, Kansas, on November 1, 1892. On March 4, 1893, Doolin married at Ingalls, the town in Payne County that the band had come to treat as a haven, and for about three years Ingalls served as its base between raids. In June 1893, near Cimarron, Kansas, the band held up another train, and Doolin came away with an injury to his foot that left him with a rheumatic leg for the rest of his life.
The federal hunt for Doolin began before he had a band of his own. In the summer of 1891 three deputy marshals who would spend the next five years on his trail joined forces and set out after the outlaws of the territories. The most seasoned of them had come to Fort Smith, Arkansas, in 1886 to serve the federal court there as a deputy marshal, and on his first expedition into the Indian country he brought back seventeen wanted men, eight of them sought for murder. By 1891 he was trailing the Daltons, and when the Daltons fell at Coffeyville he turned to the men who had survived them.
The territory's federal law enforcement was rebuilt as the band grew. On July 1, 1893, a new United States marshal for Oklahoma Territory took office at Guthrie and began assembling a large force of deputies, the senior of the three among them from that year. The three deputies had worked out a plan to take the band by surprise at Ingalls. The new marshal stopped it. He judged that more men were needed, and he set about raising a posse large enough to take the town.
By late August 1893 the marshal's office had word that the band was staying at Ingalls. The marshal dispatched a posse of thirteen men under a deputy marshal, and they came into town on September 1. Doolin and five of his men were in town, Daugherty among them.
The day left Ingalls with five dead. Richard Speed, a special deputy marshal, died in the town that day. Thomas Hueston, a deputy marshal, and Lafayette Shadley, a deputy marshal who had come to Ingalls with the posse, both died of their injuries soon after. Two people of the town were also killed, one of them a boy named Del. Several other members of the posse were injured.
The outlaws got away, all but one. Daugherty stayed behind after the others had gone. When the marshal's chief deputy arrived with reinforcements, the posse promised him protection if he gave himself up, and he surrendered. He was the only member of the band taken at Ingalls. Doolin and the rest rode out of town and kept riding.
The loss of three deputies in a single day changed the scale of the pursuit. The three deputies who had first proposed the Ingalls plan were relieved of every other duty and assigned to the Doolin case full time. Over roughly three years in Oklahoma Territory they would arrest more than three hundred wanted men between them, and Doolin's band remained their chief quarry throughout. The band kept moving, and its raids now reached from Kansas through Indian Territory into Texas.
The law dealt first with the one man in its hands. Daugherty was held at Stillwater for the deaths of two of the deputies and the boy. Stillwater was the seat of Payne County, and the territorial district court that sat there carried both territorial and federal jurisdiction. In February 1894 he was moved to the federal jail at Guthrie. In mid-May 1894 he was convicted of manslaughter and sentenced to fifty years. After he tried to break out of the Guthrie jail in June, he was sent to the penitentiary in Kansas. He was paroled in 1910.
That manslaughter conviction is the only verdict any court returned for the deaths at Ingalls. It covered two of the three deputies and the boy. No court ever tried anyone for the death of the third deputy, and none tried Doolin for any of them.
Doolin's band went on working through the winter after Ingalls. On January 29, 1894, it took the bank at Pawnee, and on March 13, 1894, it struck at Woodward, Oklahoma Territory.
On May 10, 1894, seven members of the band rode into Southwest City, in the far southwest corner of Missouri, and took about $3,700 from the town's bank. J.C. Seabourn, a man of the town, died four days later.
A posse left Southwest City within hours and followed the trail southwest into Indian Territory, but lost it beyond the Grand River. A week later the robbers had still not been heard from. A reward of $1,700 was offered for their capture. Local authorities arrested several men in the weeks that followed. One was discharged for want of evidence. A second was held until the next term of court and released when the grand jury declined to indict him. A third was indicted, but his case never came to trial for lack of evidence. Doolin himself was never charged over Southwest City. A witness in the area identified him as one of the raiders, and by the time a county history appeared in 1897 the town had come to accept that the raid was the work of Doolin and his band.
On April 3, 1895, a train was held up at Dover, Oklahoma Territory, a robbery attributed to the band. It was close to the last of the band's work. In the months and years after Ingalls the deputies captured or killed one member after another, and most of the men who rode with Doolin died violently.
Doolin spent part of 1895 out of sight in New Mexico Territory. He tried for a time to live quietly there, then went back to his old trade the following year.
The foot injury from the Cimarron robbery brought Doolin to Eureka Springs, in Carroll County, Arkansas, where a doctor's advice and the town's mineral waters drew visitors seeking relief from rheumatism. He registered under the name Tom Wilson. Word that he had gone there reached the deputies, and one of the three followed him. On January 15, 1896, that deputy, working alone, arrested him in the town, and the two left on the next train for Oklahoma Territory.
The arrival at Guthrie drew a crowd. As many as two thousand people lined the streets to see the prisoner brought in to the federal jail.
Doolin now faced two sets of charges. At Guthrie he was held to stand trial for bank and train robbery. At Stillwater, the seat of Payne County, a grand jury indicted him for murder in connection with the deaths at Ingalls, the same deaths that had sent Daugherty to prison.
The United States attorney offered him a way out short of trial: fifty years in prison in exchange for a plea of guilty. Doolin refused. He later told the deputy who had arrested him that fifty years was too long to spend in prison. He entered a plea of not guilty, and the case was set for trial.
He waited for it in the federal jail at Guthrie for a little less than six months.
The trial never began. On the Sunday night of July 5, 1896, the night before he was due in court, Doolin led a break from the federal jail at Guthrie. He had planned it, and the guards on duty were overpowered.
Fourteen men got clear of the jail. They followed the railroad tracks out of Guthrie and then split up. One of them changed his mind, turned back, surrendered, and told the officers which way the others had gone. Two deputies took up the pursuit at once, and deputy marshals had a posse in the saddle within the hour, but it found none of the men that night.
Doolin did not stay in the territory. He went south and west and hid for a time on a ranch in New Mexico Territory, the country where he had lain low the year before. Then he turned back. His wife and child were living near Lawson, in Payne County, and he crossed the Cimarron country toward them.
The deputies expected him to come. The posse came to believe that he would try to reach his family near Lawson, a town now called Quay, and the senior deputy set his watch there.
The last stage of the pursuit turned on a local man. A blacksmith near Lawson told the senior deputy that Doolin had come in, and on the night of August 25, 1896, the deputy and the men riding with him waited for him outside the town, with local men who knew the country among them. They called on Doolin to surrender. He refused, and the posse killed him.
The deputy who led the posse received a reward of a little more than $1,400 and divided it among the seven men who had ridden with him.
Doolin was about thirty-eight. He had been indicted for murder, had pleaded not guilty, and had never stood trial. The murder indictment returned at Stillwater ended with his death.
Doolin was never convicted. The murder indictment at Stillwater was never tried, and no court ever found who among the band caused which of the deaths at Ingalls. The only verdict on those deaths is Daugherty's 1894 manslaughter conviction, and it covered the deaths of two of the deputies and the boy. The death of Shadley has been laid on another member of the band who never faced trial.
The death at Southwest City was never charged against Doolin or anyone else in his band. It is attributed to the band on the strength of a local identification and the county history of 1897.
1858: born near Big Piney Creek, Johnson County, Arkansas.
1881: moves to the Oklahoma country; works as a cowboy on the Halsell ranch near Logan.
About July 4, 1891: confrontation with officers near Coffeyville, Kansas; Doolin flees.
May 1891 to July 14, 1892: rides with the Dalton gang in train and depot robberies.
Summer 1891: three deputy marshals join forces to pursue the outlaws of the territories.
October 5, 1892: the Dalton raid on Coffeyville; Doolin is not part of it.
October 1892: forms his own band.
October 14, 1892: train robbery at Caney.
November 1, 1892: bank robbery at Spearville, Kansas.
March 4, 1893: marries at Ingalls.
June 1893: train robbery near Cimarron, Kansas.
July 1, 1893: a new U.S. marshal for Oklahoma Territory takes office.
September 1, 1893: federal posse at Ingalls; three deputy marshals and two townspeople die; Roy Daugherty surrenders.
After September 1893: three deputies assigned to the Doolin case full time.
January 29, 1894: bank robbery at Pawnee.
February 1894: Daugherty moved from Stillwater to the federal jail at Guthrie.
March 13, 1894: robbery at Woodward.
May 10, 1894: bank raid at Southwest City, Missouri; a man of the town dies four days later.
Mid-May 1894: Daugherty convicted of manslaughter; fifty years.
April 3, 1895: train robbery at Dover, attributed to the band.
1895: Doolin in New Mexico Territory.
January 15, 1896: arrested at Eureka Springs, Arkansas; taken to Guthrie.
1896: indicted at Stillwater for murder over the Ingalls deaths; refuses a fifty-year plea offer; pleads not guilty.
July 5, 1896: escapes from the federal jail at Guthrie on the night before his trial.
August 25, 1896: killed by a federal posse near Lawson, Payne County.
1910: Daugherty paroled.