Pathological Counterinsurgency critically examines the relationship between elections and counterinsurgency success in third party campaigns supported by the United States. From Vietnam to El Salvador to Iraq and Afghanistan, many policymakers and academics believed that democratization would drive increased legitimacy and improved performance in governments waging a counterinsurgency campaign. Elections were expected to help overcome existing deficiencies, thus allowing governments supported by the United States to win the “hearts and minds” of its populace, undermining the appeal of insurgency. However, in each of these cases, campaigning in and winning elections did not increase the legitimacy of the counterinsurgent government or alter conditions of entrenched rent seeking and weak institutions that made states allied to the United States vulnerable to insurgency. Ultimately, elections played a limited role in creating the conditions needed for counterinsurgency success. Instead, decisions of key actors in government and elites to prioritize either short term personal and political advantage or respect for political institutions held a central role in counterinsurgency success or failure. In each of the four cases in this study, elected governments pursued policies that benefited members of the government and elites at the expense of boarder legitimacy and improved performance. Expectations that democratization could serve as a key instrument of change led to unwarranted optimism about the likely of success and ultimately to flawed strategy. The United States continued to support regimes that continued to lack the legitimacy and government performance needed for victory in counterinsurgency.