This paper is a case study that purports to investigate the problematic history of the “14 Waffen Grenadier Division der SS, ‘Galizien’” during the Second World War, with particular attention to its origins, background and its collaboration with Nazi Germany. In the history of the Waffen SS during the Second World War, the Galizien Division appeared one of the most controversial cases in that it was made of the pro-Nazi Ukrainians in Galicia, one of the allegedly “untermensch” peoples in the East according to the Nazi racial ideology. While the Waffen SS have a bunch of “untermensch” foreign divisions available, the Galizien Division was indeed sui generis, because it was created with active cooperation from OUN-M, who saw the division as a future linchpin for the building of an independent Ukrainian Army. Unlike other East-Slav divisions that were used only for anti-Partisan activities, the Division was deployed in the main front to fight the Soviet Army, especially in July 1944 at Brody, the Ukraine, a battle that forced the division to suffer from huge loss. After the battle of Brody, the division was rebuilt and deployed in Slovakia and Austria before its capitulation to the British Army in May 1945. The history of the Galizien Division was a microcosm showing the problematic nexus between the Nazi Germany and the Ukrainian nationalist movement, which had many commonalities with the Nazi.