The disagreement on the proper role of judges confronting upon issues of political morality goes back to the renowned debate between Herbert Hart and Ronald Dworkin. The generations of constitutional courts, led by ambitious chief justices in many countries, are considered the most important institutional guarantors of transitional justice and constitutionalism on account of their decisions on political morality, human rights, principles of rule of law and separation of powers. However, the constitutional adjudication is Janus-faced because the activity of the courts may contribute to the re-emergence of authoritarianism. The paper offers different case studies from Russia, Hungary and Moldova to demonstrate how chief justices deal with problems left by former authoritarian parties, during the period of emerging new authoritarianism.