The Philippines’ over a century-long tradition of democratic politics stands out regionally, with many of its current institutions created during “colonial constitutionalism” under U.S. rule. Some scholars have suggested the country’s “democratic ambivalence” can be traced back to the promissory liberalism but authoritarian practices of the colonial era. While adding an important historical dimension to the understanding of Philippine democracy’s current discontents, this path dependent argument elides the cyclical nature of the country’s politics. “Strongman” presidential rule (Manuel Quezon, Ferdinand Marcos, Sr., and Rodrigo Duterte) has alternated with opposition “democratic crusades” (linked to the presidencies of Ramon Magsaysay, Corazon Aquino and, to some extent, Benigno Aquino, III). Ferdinand Marcos, Jr.’s landslide victory in the 2022 presidential election with a campaign that invoked nostalgia for his father’s authoritarian rule has often been cited as another symptom of the country’s continued democratic regression. Yet it also highlights the cycling characteristic of the country’s politics as a counter-narrative of a developmental “golden age” after Marcos, Sr. declared martial law in 1972 rule eclipsed the tale of how EDSA “people power” uprising in 1986 “miraculously” freed Filipinos from dictatorship. A structuralist account of the innate instability of the Philippine’s oligarchy-dominated democracy offers a plausible explanation of these repeated political crises but underplays agency. “Strategic groups” - particularly the Catholic Church hierarchy, big business, and CSOs - have often allied with opposition politicians to push back against presidential aggrandizement. Utilizing a “structuration” perspective, this project examines presidential power and elite opposition as well as the prevalence of political violence and the instrumentalization of mass poverty in historical perspective. These factors have recurrently combined to lead to the fall, restoration, and now steep decline of democracy in the Philippines.