Do national leaders have an obligation to negotiate with enemies that have been villainized despite government policies and popular opinion that constrain them from doing so? This article compares the prenegotiation decision to negotiate under normal circumstances and under more trying conditions in which negotiation may be viewed as appeasement. Why enemies are villainized, the objectives of the villainizerr, the cosequences, and the “villainizer's dilemma” are examined. Four recent examples of negotiations – Israel‐PLO, U.S.‐Haiti, U.S.‐North Korea, and Great Britain‐Sinn Fein – are used to draw implications for researchers and practitioners on how, why, and under what circumstances leaders agree to negotiate with their villains, while saving face and shielding themselves from charges of appeasement.

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