We see audacious prison escapes in movies and think, that can't happen in real life. Strangely, it happens, and sometimes in ways too unbelievable for the movies. Successful prison breaks often require collaboration with outside accomplices. Or with those who are supposed to keep you inside, or at least their carelessness or incompetence. It can also require long term planning, patience, and luck.
However, breaking out of prison doesn't mean you are exactly free. Most prison escapees are apprehended sooner or later while on the run, which leads to the subgroup of prisoners who managed to escape over and over. You have to wonder how someone with an escape on their record isn't under better security, but the most talented escapees have several in their history. Honest Jack Sheppard (illustrated above) flew the coop four times! John Dillinger managed multiple prison breaks because he had a network of people willing to help him. And even Ted Bundy pulled off two of them. Read about eight of the most spectacular prison breaks at Mental Floss.
(Image credit: J. Sketch)
