This chapter aims to demonstrate the contingent role of the Thai middle class in the process of democratization and to explore the driving forces that result in its turncoat from paragons to opponents of democracy in contemporary Thai politics. This chapter tries to analyze the causes of Thai middle class rage from a socio-cultural structure approach, and verify its shift of attitudes towards democracy through three correlations – civil–military relations and democratization, political cultural and democratization, and elite politics and democratization – to relocate middle class in civil society’s role in democracy from the perspective of ‘democracy Thai-style’.