This article highlights the increasingly prevalent process of so-called“ conceptual flipsiding”: that is, of strategic reversal of notions once closely associated with liberal democracy, and of its key values of freedom, equality, tolerance, and the like, for the pronouncedly illiberal gains. Viewing the said process as part and parcel of the wider normalization of an illiberal imagination through strategic discourses and practices in and beyond the field of politics, the article contends that conceptual flipsiding increasingly allows recontextualizing and eventually normalizing a deeply illiberal understanding of polity, society, and community. Seeing these as increasingly redefined in recent years in many formerly liberal-democratic contexts by, especially, the far right and its numerous affiliates in politics, media, and/or un-civil society, the article argues for theoretical and analytical elaboration of conceptual flipsiding in order to depict its wider exploratory usability in grasping the current illiberal conceptual and discursive fluidity. The article emphasizes that, following the discourse-conceptual logic behind the conceptual flipsiding dynamics, one is able to deconstruct the ongoing infusion of key social and political concepts and discourses with new and often deeply illiberal understandings.