Christopher Daniel Gay has broken out of jail more times than anyone else alive. He is the stuff of country songs and film rights. Reporter Ben Montgomery learned about him after Chris's most notorious getaway; he had fled prison and stolen a tractor trailer so he could visit his dying mother. (Oh, and somewhere in there he also made off with Crystal Gayle's tour bus.) Running had become a way of life for Chris, and that big stunt made him into a folk hero, an underdog with seemingly good intentions, always one step ahead of the law. But the story behind the myth is more complicated. Producer Pat Walters joins Ben to unravel Chris's past. They ask him, and those closest to him, why he keeps on running, and whether he can ever stop.