This paper offers three different case studies from Hungary, Russia, and Moldova to demonstrate the special role of powerful chief justices – László Sólyom, Valery Zorkin, and Alexandru Tănase – in facing authoritarian past and the possibility of reemergence of authoritarianism. Based on these case studies, I argue that the judgments of chief justices on transitional justice had a great influence on the constitutional development of East-Central European democracies. Sólyom and Tănase were eager for transition toward constitutionalism while Zorkin, once a pathfinder for constitutional ideas, served authoritarian imposition. Though led by entirely different moral and political convictions, neither of them respected objective principles of the constitutional text but simply imposed their own personal convictions. The lesson is that during political transitions constitutional adjudication based upon personal convictions may contribute to the reemergence of authoritarianism.