The inmate tossed the self-made rope over the 18-foot cinder block wall and pulled himself up and over, remaining free for 41 days before being picked up by officials and brought back to prison.
Asked how he knew his plan would work, Shepard told the paper, "I was pretty sure about that. I think there's always ways to make a rope.
"When you take somebody and put them in here for 24 hours a day, he has nothing to do but think of some way out," Shepard said. "I think there are always ways of coming up with some idea."
"Dental floss is extremely strong when you start to braid it," said Webster, adding that many prisons have banned the sale of floss since Shepard's escape.
But rather than constructing an elaborate plan to get out of prison, Webster said, many inmates simply walk out.
"One inmate in Rhode Island recently just walked out using another inmate's release papers," said Webster, referring to 21-year-old Nayquan Gadson, who is still at large after escaping from the Adult Correctional Institute in Cranston, R.I.
"False paperwork is most common in escapes," said Webster.
That apparently was how Kevin Jerome Pullum walked out of Los Angeles' Twin Towers jail in July 2001 just hours after he was convicted for attempted murder, according to the Los Angeles Times. The paper reported he walked out using a "fake employee identification badge bearing a picture of actor Eddie Murphy from the film 'Dr. Dolittle 2'" before being captured 16 days later.
Webster said that while inmates he spent time with in prison discussed escaping, it was never with the intention of actually trying it. Having spent most of his time at a federal prison camp where there is far less security and it is possible to just "walk off the property," Webster said inmates rarely tried it.
"Inmates who try to escape are not favorites with other inmates; they're considered idiots," said Webster. "Yeah, we used to talk about it, how easy it would be to just walk away. But where are you going? 100 yards? They will catch you."
Inmates who did walk away often were provoked by what prisoners refer to as a "pool boy letter," or a letter from a wife or girlfriend on the outside announcing that she'd found another man.
"But very few of these people who escape do well," he said. "Escaping requires a tremendous amount of resources, and you can't go home again. You have to disappear. And the only places you can go where our government won't find you are not really the places you want to go."
Kenneth LaMaster, a prison historian who served as a correctional officer for three decades, much of his career spent at Leavenworth, the largest maximum security federal prison in the U.S. until 2005, has seen all types of escape attempts, even an inmate trying to get out via helicopter.
While LaMaster acknowledges that modern-day security makes it harder for inmates to escape, he still said escapes are a real concern in the prison community.
"It's really hard to do it," said LaMaster, "but wherever there's a will there's a way.
"It's a 24-hour cops and robbers issue where inmates are looking for ways to defeat us and we're looking for ways to keep them in," he said. "It's a constant battle that's fought every day."