Finally Finished: 20,000 Years in Sing Sing by Warden Lewis E. Lawes, 1932.
I'm not sure if this edition was actually printed in 1932 or not. I also skimmed the book for the last twenty pages because Lawes was wordy.
Lawes worked in the prison system for several years and was the first long-term, professional warden the prison had. All previous wardens were political appointees who would last from 6 months to two years.
Lawes traces the history of Sing Sing and penology theories. He then goes over his career and his and inmates daily routine in Sing Sing and how the prison works as a whole. His views on prisons and prison administration were practical and logical. Lawes talks about the comparative views on penology and the lock-em-up-forever vs. reform-them. Lawes was a practical guy; he knew that some convicts were incorrigable but that some were not and should be helped along. He saw arbitrary prison sentences and the absence of education and recreation in prisons as real good ways to start problems.
It'd be interesting to read Lawes comments about prisons today. Back then prison gangs were nothing like they are now and racial tensions were not so bad. I've read a couple books by Eddie Bunker that compare well to Lawes views on prison administration and convicts and the way to get both to live together. I read Newjack by Ted Conover a few years ago as well. Conover's experiences almost 70 years later that 20,000 are a neat comparison. Sing Sing's prison population are much different, the buildings even older, and Conover had frontline experience coping with inmates.
Lawes coverage of changing public perceptions on prison, the law, ex-convicts, and the courts are accurate for today.