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If You Ever Find Yourself in Prison, Keep Flossing


I almost always share current stuff in my blog posts, but I came across an older story today that was both too unbelievable and too good not to share:

In 1994, Robert Dale Shepard had prior convictions for armed robbery and manslaughter and was sent to South Central Regional Jail in Charleston, West Virginia to await trial for robbing a post office. Once in prison, Shepard purchased two 100-yard packs of dental floss from the prison commissary and traded some cigarettes to other inmates for even more packs of floss. Shepard wasn’t like Canyon Gate Dental patients though; he had more in mind than impeccable dental hygiene. After acquiring enough materials, Shepard weaved the floss into a minty waxed rope that was 48 strands thick and more than 15 feet high. On one end of the rope he tied an AA battery to act as a makeshift grappling hook.


The walls of this particular prison consisted of an 18-foot high cinder block wall capped by a chain link fence. When presented with the opportunity, Shepard tried over and over to attach the battery through the chain link portion of the fence. He was unsuccessful for some time, and then fearing capture, had to abandon his attempts to escape. In his haste he left his dental floss rope behind. The floss rope was subsequently found by prison authorities and apparently it did nothing to pique their interest or even arouse the smallest bit of suspicion because nothing happened. I repeat: prison guards did nothing after finding a makeshift rope in the yard near their prison’s fence!  I guess that’s par for the course in West Virginia though.

Two days later Shepard attempted escape again with another dental floss rope and this time was successful. He was able to hook the battery around the chain links at the top of the cinder blocks and then pulled his 5-foot-9, 150-pound frame up the wall where he cut a hole in the chain links using a 3-inch long hacksaw blade he had been concealing. Shepard had no accomplices and reported that the escape attempt took about 20 minutes total. “Getting up the rope was incredibly hard and once I got up, I was so tired, I could hardly saw the fence,” Shepard related. It was the nature of the dental floss itself that made scaling the wall so difficult. “Once I put my weight on the rope, it was really hard to climb. I was cutting my fingers up after my weight was on it.”

Although the escape attempt was successful, Shepard was later apprehended at gunpoint after 41 days of eating berries in the forest for survival and bathing in rivers. During his time “roughing it” he also robbed a pharmacy. After he was caught, he used his phone call to dial the Associated Press and in his conversation with a reporter, he referred to himself as Spiderman. Two additional charges of attempted escape and robbery were added to his tab and very surprisingly, Shepard was unsuccessful as he represented himself in court against these charges. Three jail employees were suspended for their stupidity, razor wires were installed above the recreational areas where Shepard scaled the wall, and dental floss was denied to inmates after the incident. Shepard was given solitary confinement and only leaves the cell when handcuffed and shackled. He is scheduled for release in 2020.

Although they are wacky, the events of this story all seem plausible to me except for one detail: I went to dental school in Louisville, Kentucky, which borders West Virginia; I’ve seen enough West Virginian smiles that I have a really hard time believing there is enough dental floss in that whole state to make a rope that long.

-Nicolas K. Young, DMD

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