Ivy Bluff: This Week in the Archives (December 2019)

Ivy Bluff 1959 AP Photo

Dec. 24, 1959

A Watauga County man who was one of 20 convicts who escaped from the Ivy Bluff Prison in Caswell County gave himself up to Watauga County and FBI officers in late December 1959, the Watauga Democrat reported.

Law enforcement officers had been searching for the man and two other convicts who were still at liberty since Dec. 8. The prison break resulted in the dismissal of several prison officials, including the superintendent, the newspaper reported.

The Watauga County man was reported to have gone to West Virginia after the break, where he hid out in barns, before stealing a station wagon in Virginia and heading back to North Carolina. Sheriff’s Deputy Emmett Oliver and FBI Agent Bob Moore found the man in a station wagon on a rural road, and when Oliver tapped on the car's window with his gun and ordered the man to come out, the man reportedly put the car in reverse in an attempt to run over Moore and escape. Moore shot through the rear window and the escaped convict surrendered without reaching for the loaded .38 pistol in his right jacket pocket, the newspaper reported.

"The pistol was identified as one stolen from the prison during the mass break," the article stated.

Ivy Bluff, according to a 2017 feature in the Raleigh News & Observer, was once called "Little Alcatraz" and, with steel walls, steel doors and concrete walls, was thought to be "escape proof." But that was before Charles "Yank" Stewart, who had already escaped confinement six times, led the group of 20 felons through the gates at Ivy Bluff — "a breakout still unequaled in state history," the News & Observer article stated.

"In December of 1959, he sawed through three bars with a smuggled hacksaw, passing the blade to a fellow prisoner. As the blade made its way down the row of cells, Stewart called a guard for some toilet paper. When the guard passed, he squeezed through the hole he had cut and grabbed the guard by the feet, forcing him into a cell as the other freed inmates joined in," the newspaper recounted.

"With the guard's keys, the prisoners passed through three more doors, then jumped two more guards to pass through two more. Using three captured guards as a bargaining chip, the escapees forced a sergeant to call the officers manning the towers down for a cup of coffee. And once Stewart found himself in charge of the entire prison, he invited every inmate to leave. A truck carted 20 prisoners away," the story continued.

Stewart was found a few days later, and would spend another 12 years behind bars, "including a stint in the real Alcatraz, where he painted landscapes and the Last Supper. He finished life as an elderly gardener for the city of Wilmington, tending roses until he died in 1985."

Source: Oakes, Anna. "This Week in the Archives," Watauga Democrat, 26 December 2019.