Powerful corporations leverage the law to shape the regulatory environments in which they operate. A key strategy for achieving this is litigation. I ask under what conditions corporations litigate, and specifically, what happens when two repeat players, transnational agribusiness firms and local governments, face each other in court. I compare outcomes of two cases—Hawaii and Arica, Chile—documenting how different sociopolitical contexts and legal systems shape how actors engage the law. Interviews with firm managers, unions, government officials, lawyers, and advocacy organization leaders and document analysis reveal that firms seize on existing institutional norms and politics to define their localized legal strategies. Through strategic legalism, a defensive legal strategy that is outcome‐oriented and context‐specific, firms accomplish legal compliance and political containment of their opposition. In Hawaii, firms rely on preemptive legality, a strategy that moves controversial issues like pesticide safety from one domain of democratic politics to another that is largely incontestable because it is preempted by a higher authority. In Chile, firms use authoritarian legality, an approach that draws on authoritarian structures and policies within the state, to sway legal outcomes. These cases reveal the 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.