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In November 2012, voters in the states of Colorado and Washington passed ballot initiatives to legalize recreational marijuana industries. Since then, eight additional states and the District of Columbia have followed suit, and many more have seen legalization debates in their legislative halls and among their electorates. Over twenty bills recently introduced in Congress have sought to break federal marijuana laws away from prohibition. Although the national debate is indeed a vibrant one, it has neglected to address how legalization may be jeopardizing the compliance status of the United States under international drug treaties, and what the consequences may be if legalization means breach. For decision-making over marijuana policy to produce creditable outcomes, it must take into consideration the factor of international relations. Subnational conduct implicating treaty commitments is in fact not without precedent in America, and one episode in particular—notable for its contributions to the nation’s constitutional origins—reveals how treaty noncompliance can degrade a nation’s diplomatic standing. This article examines both past and present controversies and uses the advantages of historical perspective to draw international drug law issues into the legalization debate.