After his book was published, Osborne was appointed Warden of Sing Sing prison in Ossining, New York, on December 1, 1914, replacing Judge George S. Weed. Sing Sing was built on the east bank of the Hudson River, approximately 30 miles north of NYC. The original cell block was built by prisoners from Auburn Prison in 1825. Although Osborne had tried to change the worst conditions in New York state prisons while he was the chair of the governor’s commission, still when he arrived at Sing Sing it continued to be a very brutal place for the 1,500 inmates it held (Tannenbaum, 1933). It was a prison that took its toll on both prisoner and staff. Of the 31 previous wardens who ran Sing Sing before Osborne, the average term was a little over one year.
