Bill Doolin escapes from jail - Jul 05, 1896 - HISTORY.com

The famous outlaw Bill Doolin escapes from an Oklahoma jail after only a few months of captivity.

Like many outlaws, William Doolin only gradually fell into a life of crime. Born in Arkansas in 1858, the tall and slim Doolin went west at the age of 23. He found work as a cowboy on several Oklahoma ranches and was widely regarded as a trustworthy and capable employee.

Doolin’s life course changed forever when a beer party in southern Kansas turned violent and two deputy sheriffs ended up dead. Doolin’s exact role in the murders was unclear, but evidence of his guilt was substantial enough to raise the chance of prison. Unwilling to risk a trial, Doolin became a fugitive.

Cool, intelligent, and a skilled shot, Doolin was suited to the outlaw life. Traveling throughout the West, he robbed banks and trains, sold illegal whiskey to Indians, rustled cattle and horses, and killed several men. He formed a criminal gang that occasionally joined forces with the Dalton brothers to rob banks in Oklahoma and Missouri.

As a robber, Doolin was more successful than most because of his careful planning, but success inevitably attracted the unwanted attention of the law. In January 1896, Doolin returned to Arkansas. While Doolin was taking the medicinal waters at a resort called Eureka Springs, the famous Oklahoma lawman William Tilghman arrested him without a struggle.

Tilghman transferred Doolin to a jail at Guthrie, Oklahoma, to await trial. On this day in 1896, Doolin managed to escape, but was free only for a short time. A few weeks later, on August 25, a posse caught up with Doolin at Lawson, Oklahoma. Doolin resisted arrest, and in the ensuing gun battle, lawmen shot him to death.