In the Second World War, the Chinese Nationalist government mobilized more than 4,000 Chinese college students as interpreters for the American and British Allied forces in the China-Burma-India theater. Discharged after V-J Day, most interpreters resumed and completed their education while China descended into civil war. By 1949, most of the former interpreters remained in China, while some 200 fled to Taiwan and over 100 studied or worked in the United States. In the wake of China’s intervention in the Korean War, the United Nations Command (UNC) was in desperate need of Chinese linguists. However, Washington avoided mobilizing Chinese interpreters within the United States, leaving the task to General Douglas MacArthur, who hired more than 70 linguists from Taiwan, mostly former WWII interpreters. These interpreters served not only at the UNC headquarters in Tokyo but also on the front lines, in POW camps, and in the negotiation tents at Panmunjom, leading to the rise of the anti-Communist POWs and the prolongation of the armistice negotiations and the war. On the Chinese Communist side, a small number of former WWII interpreters served as POW interrogators and medical doctors. Drawing on archival documents, newspapers, and memoirs, this talk traces the divergent and intertwined paths of three former interpreters from the Second World War to the Korean War and the Cold War. It reveals the multifaceted encounters between the Chinese interpreters and the Americans, as well as among the interpreters themselves, first as comrades and later as allies and enemies.