The right to counsel maintains an uneasy relationship with the demands of trials for war crimes. Drawing on the author's personal experiences from defending a Guantanamo detainee, the Author explains how Gideon set a baseline for the right to counsel at Guantanamo. Whether constitutionally required or not, Gideon ultimately framed the way defense lawyers represented their clients. Against the expectations of political and military leaders, both civilian and military lawyers vigorously challenged the legality of the military trial system. At the same time, tensions arose because lawyers devoted to a particular cause (such as attacking the Guantanamo trial system) were asked at times to help legitimize the system, particularly when it came to decisions about whether to enter a plea to help legitimize the rickety trial system in operation at Guantanamo.