The illiberal tendencies in various Central and East European (CEE) countries have re-invoked concerns about the region sliding back to the “old ways” or, as some surmise, always having lacked fundamental democratic features in the first place. This chapter turns to the political thought of two writers-cum- presidents, Václav Havel and Lennart Meri to tap into the early post-1989 visions of Europe, democracy and responsibility. Havel’s call for a post-totalitarian “existential revolution” and Meri’s bold propositions about the telos of Europe serve as critical counterpoints amidst contemporary pessimism about the faint grasp of democracy in the eastern part of the continent. Revisiting the visions of Europe articulated by these representatives of CEE at a critical juncture in the European history provides an intellectual stimulus for rethinking the current impasse along the East-West axis of Europe. At the time of CEE’s increasing association with political regression, the political writings of Havel and Meri offer an important counterpoint to the loudening national populist voices of today’s political entrepreneurs.