Feminist scholars have theorized extensively about how the military, war, and especially the combat experience enhance the militarization of masculinities, less scholarly attention has been devoted to men whose identities were highly militarized in the context of a political conflict and turbulence. Based on over two decades of extensive field research in Israel, Palestine, the North of Ireland, and the United States, this study charts the processes and practices involved in the militarization and de-militarization of men and masculinities. Arguing that the multiple systems of domination and oppression, including sexism, racism, and homophobia have often been using during the process of militarization and military training, the process of de-militarization has to explicitly call into question not only war and political violence but also unpicks other systems of mental and emotional domination and oppression. The analysis is situated in relation to historical, sociopolitical, and economic conditions that enhance and/or undermine de-militarization efforts and concludes with a chapter addressing the policy impact to peacebuilding in these territories.