This article examines the Sugamo Shimbun (the Sugamo Weekly News), written by Sugamo prisoners between 1948 and 1952 during the Allied occupation of Japan, in broader domestic and international political contexts. The prisoners questioned the legitimacy of both Allied and Japanese authorities as the United States initiated its Cold War strategies with Japanese government support. The newspaper demonstrates that the concept of "democracy" as promoted by the Allies during their occupation of Japan came into question around the time of the Korean War in 1950. Nonetheless, the prisoners’ sense of responsibility in World War II was not impartial. By examining the prisoners’ voices in the Sugamo Shimbun and the power dynamics inside the prison, this article focuses on where the prisoners’ sense of guilt originated—as a result of the prison’s correctional programs—and how the voices of the prisoners more or less reflected national and international politics of that time.