Previous decades' celebrations of the triumph of democracy were frequently based on mainstream analyses that displayed two major theoretical problems. First, conceptualisations of democracy based on ‘minimal pre-conditions’ commonly conflated the formal establishment of democratic structures with the far more complex and historically challenging creation of substantive democracy. Second, a deductive and generally ahistorical model asserting fixed stages of ‘democratic transition’ diverted attention from deeper and more substantive examination of struggles for power among social forces within specific historical contexts. By adhering to minimalist conceptions of democracy and simplistic models of democratic change, mainstream analysts quite often chose to overlook many underlying limitations and shortcomings of the democratic structures they were so keen to celebrate. Given more recent concerns over ‘authoritarian undertow’, those with the normative goal of deepening democracy must begin by deepening scholarly conceptualisations of the complex nature of democratic change. This analysis urges attention to the ‘source’ and ‘purpose’ of democracy. What were the goals of those who established democratic structures, and to what extent did these goals correspond to the ideals of democracy? In many cases throughout the world, ‘democracy’ has been used as a convenient and very effective means for both cloaking and legitimising a broad set of political, social, and economic inequalities. The need for deeper analysis is highlighted through attention to the historical character of democratic structures in the Philippines and Thailand, with particular attention to the sources and purposes of ‘democracy’ amid on-going struggles for power among social forces. In both countries, albeit coming forth from very different historical circumstances, democratic structures have been continually undermined by those with little commitment to the democratic ideal: oligarchic dominance in the Philippines, and military/bureaucratic/monarchic dominance in Thailand. Each country possesses its own set of challenges and opportunities for genuine democratic change, as those who seek to undermine elite hegemony and promote popular accountability operate in very different socio-economic and institutional contexts. Efforts to promote substantive democracy in each setting, therefore, must begin with careful historical analysis of the particular challenges that need to be addressed.