The precarity of rule of law in the Philippines did not simply arise with the election of the country’s current president, Rodrigo Duterte. The ambivalence between reverence and irreverence for the law has been characteristic of the internal legal culture of Philippine legal and political actors, which gradually developed over time. Since the colonial period under the United States, this legal culture has been highlighted in many political junctures in Philippine history and politics. Employing historical and textual analyses, this paper examines the rule of law under Rodrigo Duterte’s presidency through the lens of Philippine legal culture that developed historically. It traces this development from the colonial period through key political junctures in the Philippines to show its reinforcing effect. It further problematizes this legal culture’s implications for the rule of law in a constitutional democracy and how it gets undermined.