Apparently the county jail has a long history of escapes.
The Caddo Herald
December 4, 1914
Eight Get Out of Jail
At 4 o’clock Wednesday morning eight prisoners escaped from the county jail and so far not a trace of the men has been found.
The escape was effected when jailer Clark lay down in the vestibule and went to sleep. He was about four feet from the jail door and the prisoners secured a long wire and hooked it onto the key ring in his belt, drew the keys inside, opened the big door, and made their getaway.
These are the men who escaped: Fletcher Watson, bad check artist; Guy Russell, charged with adultery; Will Ray, charged with stealing two bales of cotton; C. H. Thomas, charged with theft of a coat; Roy Fuller, for transporting; men giving names of Story, Angel, and Harness who were charged with bootlegging. Twenty men were left in the big cell, but they refused to go, one of them being Cliff Moye. Some of them were asleep and did not know anything about the delivery until they awoke.
Sheriff Hart, as soon as he was informed, stared a search. Durant Democrat
(Note: Edited, Feb. 19 to correct an error.)