After more than five years of authoritarian rule, rent-seeking, and a kind of ‘gangster’ neoliberal economic policies, the strongman rule of Rodrigo “Digong” Duterte has begun to unravel as the Philippines gears up for the national elections in May 2022. Realignments of social and political forces are beginning to reconfigure the political landscape amidst the continuing Covid-19 pandemic. Progressive and traditional social forces are drawing their political lines as the mounting opposition against Duterte expands. This conversation with Joel Rocamora, a renowned author, political analyst, and progressive governance practitioner, seeks to examine the rise of Duterte’s authoritarian governance, the reconfiguration of the Philippine elite and other social classes, the political/ideological debates within the Philippine Left, and the political realignments towards the Philippine presidential elections in 2022.