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In 2018, Poland and Hungary were sanctioned for their breach of European Union rule of law under Article 7, Turkey moved onto a Presidential system reversing its century old Parliamentary system, and Western Balkan countries are on an uneasy path of political change. What is happening to the transformative power of the EU? This is a question raised by many pundits who are interested in the European Union’s role in democratization process as well as the challenges that newly democratizing countries face in their internal and external policies. While Turkey has always constituted a unique example of a country of contrasts, Muslim but secular, economically developed yet democratically struggling, of Europe but not yet in Europe, neither fully in the Middle East, nor completely out it, the multiple layers of complexities in the Turkish political system has never been so profound nor more visible. Similarly, Central European countries seemed to be on a path of democratic consolidation supported by their EU accession, and the wave of popular support to get rid of the authoritarian tendencies of the past. Western Balkan countries have unique challenges on their own, overcoming ethnic tensions and consolidating their state structures. Yet, there now seems to be a common ground that even new member states of the EU in Central and Eastern Europe, and aspiring candidates such as Turkey no longer comply with the EU’s basic democratic principles, and despite the flow of funds to strengthen democratic institutions, a reversal of earlier political and judicial reforms combined with a rise of populism leading to backsliding into authoritarianism in the European periphery is clearly visible. The main questions that the paper deals with are: (i) Under what conditions does the process of democratic consolidation lead to a point of no return where underlying authoritarian tendencies are fully controlled? (ii) What are the key dynamics in these political systems that might prevent democratic consolidation, specifically in terms of liberal democracy? (iii) What are the key lessons one could draw from the European political experience that could be applicable for lapses into authoritarianism in other parts of the world? The paper proposes that the road to authoritarianism involves a process of consolidation of power in a few hands, rise of populism and the elimination of the remaining checks and balances in the political system coupled with weak external anchors. In this way, the process of democratic consolidation in these European countries paradoxically evolve towards a process of authoritarian consolidation. The findings of the paper are relevant to similar transformation in other countries, and shed light onto the complexities of democratization in the European periphery.