In late 1800s, American Prisons grew bigger and bigger to accommodate the growing crime problem. Inmate population increased over time and wardens had to take measures in order to discipline the prisoners. Especially in Sing Sing, which is the third state prison of New York, various methods to handle prisoners were applied from "Silent System" to "Mutual Welfare League". The creators of these methods believed in what they did, but there is still a controversy about their appropriateness. When we examine the history of Sing Sing, three wardens seem to be conspicuous: Elam Lynds, Thomas Mott Osborne and Lewis Lawes. Although all of them blazed trails in different ways, the most realistic one is Lewis Lawes because he was neither too strict like Lynds nor too idealistic like Osborne; however, this is not to say that Lawes' method was also the best one. Osborne was a real pioneer because his attitude needed serious courage in the time he had been living in, and that makes his vision the best.…