This article explores the apparent paradox of how Hans J. Morgenthau, who was both a proponent of realpolitik and a member of the establishment, became a prominent opponent of the American war in Vietnam. Morgenthau is perhaps best known as the author of the influential text Politics Among Nations. In the 1950s, he served as a State Department adviser and a member of the Council on Foreign Relations, but he was also one of the first American observers to express publicly his misgivings about US policies in Southeast Asia, publishing his earliest article on Vietnam in 1956. In this and subsequent articles, Morgenthau argued against understanding Asian politics in terms of ideological conflict between communism and democracy. In Vietnam, he saw a civil war in which the United States, captive to its Cold War illusions, had chosen the wrong side. Over the course of the next decade, Morgenthau played a significant role in opening public space for opposition to the Vietnam War, a role that has been largely overlooked by historians of the period. Morgenthau acted as an opinion-maker among American intellectuals, yet his critique of the war ironically failed to satisfy either hawks or doves. By the end of the 1960s, Morgenthau found himself ostracized by an establishment bent on victory in Vietnam and mistrusted by an increasingly radical antiwar movement.