May 30, 1893
The “Three Guardsmen” were tough and experienced Marshals Bill Tilghman (1854–1924),
Doolin was born in 1858 in Johnson County in north western Arkansas to Michael Doolin and the former Artemina Beller.
Doolin left home in 1881 to become a cowboy in Indian Territory, having been employed by cattleman Oscar Halsell, a Texas native. During this time, Doolin worked with other cowboy and outlaw names of the day, including George Newcomb (known as “Bitter Creek”), Charley Pierce, Bill Power, Dick Broadwell, Bill “Tulsa Jack” Blake, Dan “Dynamite Dick” Clifton, and the better-known Emmett Dalton.
Doolin’s first encounter with the law came on July 4, 1891, in Coffeyville in southeastern Kansas. Doolin and some friends were drunk in public, and lawmen attempted to confiscate their alcohol. A shootout ensued, and two of the lawmen were wounded. Doolin escaped capture by fleeing from Coffeyville. Shortly thereafter, Doolin became a member of the Dalton Gang.
On October 5, 1892, the Dalton Gang made its fateful attempt to rob two banks simultaneously, in Coffeyville, Kansas. The robbery attempt was an utter failure, with a shootout ensuing between Coffeyville citizens and lawmen, and the outlaws, leaving four of the five gang members dead, with the exception of Emmett Dalton. Historians have since indicated that there was a sixth gang member in an alley holding the horses, who escaped. Who this sixth man was remains unknown to this day. Emmett Dalton never disclosed his identity, but speculation continues that it may well have been Bill Doolin.
Oklahoma Territory, where they hid out at the house of Yantis’ sister. Less than one month later, the gang was tracked to that location. In a shootout Yantis was killed, but the rest of the gang escaped.
Two teenaged girls known as Little Britches and Cattle Annie also followed the gang and warned the men whenever law-enforcement officers were in pursuit. Sources indicate that it was Doolin who gave the young bandit Jennie Stevens her nickname of Little Britches.
Following that robbery, the gang embarked on a spree of successful bank and train robberies. In March 1893, Doolin married Edith Ellsworth in Ingalls, Oklahoma. Shortly thereafter, Doolin and his gang robbed a train near Cimarron, Kansas, during which a shootout with lawmen resulted in Doolin being shot and seriously wounded in the foot.