The author demonstrates the inescapably social and political contexts of curricular efforts at teaching thinking, specifically critical thinking. Going beyond the scope of the extant scholarship in education, he focuses on the subject's epistemological and pedagogical dimensions and he argues that the literature needs to problematize the discourse on critical thinking emblematic of cultural theses involving dominant political ideology and normative conceptions of social order. He suggests that critical thinking can be considered as a form esoteric knowledge; its modes of analysis carry the potential of yielding alternative formulations of the social world. The emancipatory thesis of critical thinking can potentially challenge the government's neoliberal and illiberal ideals and definitions of the common good qua economic and material wealth that finds little affinity with Singapore's educational discourse. He explains how critical thinking is conceptualized, taught and regulated in two Singapore schools by a unique set of neoliberal, illiberal and meritocratic socio-political ideologies.