Thomas Mott Osborne is remembered today as a dynamic force in American prison reform (Fuller, 2013). However, his path to that destiny was out of the ordinary, maybe even a bit bizarre. He didn’t work in a prison until he was 55 years of age and only after he had had a successful business career and following his becoming an influential force in both New York state and national politics. And if his path to becoming a prison reformer was odd, then his methods of learning about prison life was even stranger. He was born on September 23, 1859, in Auburn, New York, the third of four children in the family of David M. Osborne and Eliza Wright Osborne. The city in which he was born and raised, Auburn, was a center of progressive political activity,