This chapter examines the role of the middle class in the Philippine Left movement in the country’s democratization process, i.e., from 1986 onwards, through its engagement in the civil society arena. Focus is placed on a middle-class led Left movement, whose progenitor comes from the Communist Party of the Philippines (CPP), its military arm the New People’s Army (NPA), and its illegal united front, the National Democratic Front (NDF), collectively the CPP-NPA-NDF. It examines the extent to which the strategies pursued by this Left movement have been successful in confronting the obstacles to Philippine democracy.