This article contributes a new layer to the existing analyses of Duterte's foreign policy by arguing that he epitomized a transactionalist approach to Philippine foreign policy. This approach favored bilateral to multilateral relations, focused on short‐term wins rather than long‐term foresight, adhered to a zero‐sum worldview, rejected value‐based policymaking, and did not follow a grand strategy. Most of these qualities have been apparent in Duterte's relationship with China, Russia, and the United States but became even more prominent during the COVID‐19 crisis. The analysis revealed that Duterte's transactionalist foreign policy rhymed with his domestic politics, and his obsession with winning now resulted in contradictions in his foreign policy, indicating a lack of a grand strategy that informed his decision‐making. This article contributes a real‐world case of a transactionalist foreign policy while considering whether it would persist in future policymaking in the Philippines.