Jailbreak! Castleberry and Allsup on the Run!

By Anne Adams

The excitement started on a Monday afternoon in February 1936 when Lee Castleberry and Wymon Allsup broke out of the Henderson County jail. According to the February 20, 1936, Athens Weekly Review article, the pair, as “hijackers,” had successfully escaped from the Henderson County jail, climbing to the jail roof and then catching an outbound train. And that meant that they were in and out of local headlines for the next few months, causing the excitement.   

The adventure began several days before when Castleberry and Allsup (sometimes given as Alsup) had been captured within three hours after they held up a local gas station. But though they were soon lodged in the Henderson county jail they weren’t there long.

According to other prisoners, Castleberry and Allsup, both 23, made very precise plans. The night before the breakout, Castleberry placed an empty Bull Durham tobacco bag in the door of his jail cell in such a way that it could not be secured.  Then when jailers came for prisoner Richard Payne because he had visitors when the jailer closed the door it did not completely lock.

The details were ingenious. The two inmates made their escape by “gaining entrance to the main lobby surrounding the tier of cells in the jail and then crawling over the top of the cells to reach an air chamber in the ceiling and [thus] made their way to the roof of the jail.”  Then they tied blankets together to form a rope and then descended from the roof; then once on the ground, they made a dash for a passing freight train and climbed aboard as it slowed for a crossing.

Yet though officials thought they would stay on the train, actually they jumped off just outside of town.   Then apparently the pair separated.

Meanwhile, Richard Payne, held on a charge of auto theft, had trailed Castleberry and Allsup to the roof but to get down he had to tie together one of the blankets torn by the escaping pair. Then once on the ground, he ran around to the jail office to notify officials.  Payne was later given a suspended sentence for his assistance and Sheriff Jess Sweeten and his men spread the word of the escape. 

Other details came out, such as how the pair had actually escaped through a hole that had originally been barred.  “These were sawed into,” wrote the reporter, “some four years ago when …three men escaped in a similar manner. The bars had never been replaced because it is impossible to reach the opening unless the outer door to the cells is left open.”

Castleberry was picked up in Dallas a few days later and when he was returned to Athens he told his story to Henderson County attorney Miles B. Smith and other officials. As related in other Review articles, he described how he had just left an Oklahoma penitentiary where he learned the trick about blocking the jail door. Then he stole a car to head to Tyler to pick up Allsup, who he knew from when they were both previously incarcerated in a Texas prison.

Castleberry told officials that actually after jumping off the train he hid nearby and even watched the officers searching for him. In fact, the searchers actually came within a few feet of the escapees.

Then after dark just after the escape, he emerged from hiding and then stole a car in Athens and escaped to Dallas where he was then captured. “I had been driving around town for an hour and a half when they picked me up,’ he concluded.” There he was stopped by two Dallas police officers who had just received a notice on their radio that Castleberry was wanted.  

However, for his part, Allsup wasn’t free very long. An article from the February 1936 Review related that Wymon Allsup had fled to Louisiana where he surrendered to authorities two days after the escape. There his relatives told officials that they wanted to call in a Dallas psychiatrist to examine him. His mother informed the court that Allsup “had not been mentally right” since he was injured in a fall at the age of eight years.

So what about their original charge – them being “hijackers”? For that, they were charged with holding up a Texaco gas station the week before their escape. Upon arriving at the station, after the operator put fourteen gallons of gas and a pint of oil in their car, suddenly the man “found himself face to face with a pistol type sawed-off shotgun in the hands of Castleberry, who asked, ‘Got any money?’”

A visitor to the station first thought it was a prank, but soon changed his mind when Castleberry threatened him. The robbers stole about $15 from the station operator’s pocket but didn’t notice the money and valuable watch the visitor had. However, the robber did curse him for not raising his hands fast enough.  Then, stuffing the operator and the visitor in a closet, the bandits fled.

Just minutes after the holdup county officials were informed and as the word spread the bandits were picked up soon after in Palestine and returned to Athens where they were lodged in the Henderson County jail. From there the adventures began!