This paper conceptualizes intellectual dissent as a galvanizer of academic freedom in a post-totalitarian academia that is moving toward democratization. Drawing on the case of Ukraine, the analytical narrative describes difficulties in overcoming legacies in universities emerging from repressive rule that discouraged creativity, initiative, and critical inquiry, and having to envisage a transition to democratic governance in the context of neoliberal geopolitics. The case analysis suggests that intellectual dissent is essential but limited in its ability to establish the praxis of academic freedom under increasing control by oligarchic governments and a self-serving bureaucracy. By exploring interdependencies between intellectual dissent and academic freedom, this paper lays ground for an analytical framework that can be helpful in rethinking the prospects of universities at the crossroads of authoritarianism and democracy.