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This study asks how powerful corporations use the law to shape the regulatory environments in which they operate, and specifically, under what conditions they litigate. I ask what happens when powerful corporations and local governments face each other in contests to redefine the rules of the game, proposing a distinction between repeat players with greater resources and those with less. My account is based on an extended case study of the genetically modified corn seed industry in Hawaii and Arica, allowing me to compare repeat playing outcomes across civil and common law jurisdictions. I argue that firms turn to the law when confronted with resistance to accomplish legal compliance and political containment through a strategy I call strategic legalism. Strategic legalism is a legal strategy that is reactive, outcome oriented, and context specific, taking different forms in different places. By bringing the literatures on repeat playing, legal endogeneity, and legal adversarialism into conversation, I show how firms use legal tactics to seize on already existing legal and political structures as opportunities (and constraints), affecting the ways “the haves” come out ahead. This case sheds new light on the institutional and political mechanisms that corporations draw on to institutionalize their power advantages through the law, offering a typology for future scholars to better understand how the strategic behavior of corporations shapes regulatory outcomes.