Sitting under an old oak tree on a breezy spring day, in an out of the way corner of a park in Brownsville, Texas, he strums away on a guitar that looks nearly as old as he is.

With a gaunt face, scruffy, grey beard and a cigarette hanging loosely on his lips, he sings about the hardships of life and the kindness of strangers.

His black fedora, rolled coat sleeves and leather bracelets give the impression of a washed-up D-list rock star trying to hold on to his better days.

But, there are no bright lights in this drifter’s dark back story.

In the 80’s, Jeffrey Cutlip spent ten years behind bars for a violent Oregon burglary and sexual assault. He was out for just seven months before he robbed two people at gunpoint in 1993 and was sent back for another six-year term.

When he was released for the second time, Cutlip decided to take his show on the road, heading to sunny New Mexico.

For three years he let his wanderlust run wild and managed to duck the requirements that he register as a sex offender, until he could hide no longer.  In 2004, his disability payments were cut-off, so he snuck back into Oregon to get them reinstated.  But first, he would have to face the music for his wandering ways.

Cutlip told the parole board he wanted to live a quiet life and he tried to be good, but there were just too many rules he had to follow. Rules set by the state. Rules set by the shelter where he was living.

He just wanted to be free to spread his music.

But, that would have to wait. Cutlip was sent back for another 4 months behind bars.

And, once he was released, he was gone again.

Until, July of 2012, when he called 911 to turn himself in for horrible crimes he had committed decades earlier.

He had already done the time for the robbery, burglary and sexual assault.

Could this simply be the ramblings of an aging imagination?

Or was there something more sinister on the mind of this mild-mannered drifter?

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