Ted Bundy was one of the most terrifying people of all time because of his ability to appear totally normal — even charming. According to Britannica, Bundy sexually assaulted and murdered at least 28 women, and possibly many more. Despite the grievous nature of his crimes, Bundy was able to escape from prison twice — and came very close to a third attempt.

As reported by Bustle, Bundy was caught with maps and other documents suggesting he was planning an escape in Utah in 1976, and was placed in solitary confinement before he could put his plan into action. He was extradited to Aspen to stand trial for the murder of Caryn Campbell in 1977. Since he was assisting in his own defense, Bundy was permitted access to the law library at the Pitkin County Courthouse — unshackled, which meant he wasn’t restrained in any way. One day, when his guard stepped outside for a smoke, Bundy simply jumped out a window, spraining his ankle. Bundy fled and sheltered in a cabin for six days, then hobbled back to Aspen, tried to steal a car, and was recaptured.

According to Yahoo!, Bundy escaped from prison again a few months later — but this time it wasn’t an impulsive decision. Noticing a gap in the ceiling of his cell, he stopped eating in order to lose enough weight to fit through it, stole a set of clothes from a guard, and simply walked out of prison. He managed to stay free for the next two months before being recaptured.