After capturing outlaw Bill Doolin, Deputy Bill Tilghman escorted him to Guthrie, Oklahoma Territory. A large crowd, as many as two thousand people, line the streets there to see the "king of the outlaws," and cheered as Doolin was taken to jail to stand trial for bank and train robbery.

Doolin would not remain behind iron bars, however. On Sunday night, July 5, 1896, he engineered his escape. Four prisoners overpowered and disarmed the jail's night guard. The other guard was in the bull pen of the jail and upon realizing what was happening tried to run out of the unsecured area. Doolin beat him to the door, closing and locking it, which left the guard helpless and unarmed among the prisoners.

Doolin then grabbed a revolver and ordered the night guard to open the combination locks, putting the gun to his chest and ordering him to "Open the locks or die." The guard complied, setting nine prisoners free. Two of those prisoners took the big front door key from one of the guards, went back to the bull pen and invited the thirty-five prisoners still there to go with them. When all refused they locked one guard in the bull pen and the other in a cell. The gang then took a half dozen coats, vests and hats belonging to the jailers and guards, took any available weapons and ran from the jail.

One of the prisoners changed his mind during this time and proceeded to warn the proper authorities what was happening. A crowd soon gathered at the jail but it was half an hour before the jailer arrived to release his two guards. A total of fourteen prisoners escaped, including Dynamite Dick, the famed cattle rustler and bank robber. Apparently the escapees followed the railroad tracks out of town before splitting up. One other prisoner decided to turn back to the jail and surrendered, telling the officers what direction the inmates had taken. Deputies Heck Thomas and Bill Crane went in fast pursuit.

Doolin, Dynamite Dick and W.H. Jones, charged with counterfeiting, held up a buggy occupied by a young man and woman a mile from town. Brandishing a revolver and hatchet, the three outlaws ordered the couple out of the buggy and sped north in the rig, eluding capture.

Juliet Galonska
March 1996

This sketch is part of a series, “Fort Smith Minutes,” originally developed by the park staff to provide one minute long public service announcements for local radio stations. These sketches provide a light and entertaining glimpse into the complex history of Fort Smith.