The decision to negotiate instead of continuing a violent struggle often requires significant political change. The enemy may include terrorist groups, drug and weapon traffickers, human rights violators, and individuals and groups who export revolution to unstable regions. The United States maintains several categories, most defined by national laws or international agreements, by which it officially designates villains. Rogue states or groups identified as villains, however, do not usually view what they are doing as unacceptable or wrong. As the result of being villainized, states or groups may be subject to sanctions and restrictive actions. The decision to negotiate with villains, through either official or unofficial channels, requires a reversal of the villainization process. Four examples of negotiation are described that include Israel and the Palestine Liberation Organization, the United States and Haiti, the United States and North Korea, and Great Britain and Sinn Fein. Implications are drawn from the four examples so that researchers and practitioners can understand how, why, and under what circumstances leaders agree to negotiate with villains while saving face and shielding themselves from charges of appeasement. 31 references and 7 notes