This paper treats East-Central Europe as a region and investigates its common historical trajectory in the last decades. After 30 years of systemic change and 15 years of EU membership, it is high time for the re-evaluation and reconceptualization of the Europeanization and Democratization process in ECE. It is the key to understand the false start as the original sin in democratization and the reasons of ECE divergence from mainstream EU developments in order to prepare the redemocratization process. The progress of the Europeanization and Democratization process in ECE has been widely described in official documents, but for a balanced and complete picture it is necessary to present also the De-Europeanization and De-Democratization process from the very beginning. Basically, after the collapse of the bipolar world order in 1989, the Eastern enlargement was an economic and political necessity as a substantial part of the EU deepening and widening policy. The EU needed the extension of its economic space and political system that had also been pre-programmed in the mission statement of the Rome Treaty. At the same time, the new member states (NMS) needed the “Return to Europe” for their reintegration into the Western world. However, the capacity for this extension was actually missing on both sides, and it has remained so during the last 30 years of systemic change or the 15 years of EU membership. Altogether, this controversial process has produced a colorful picture of successes and failures in all NMS that will be analyzed in an ECE context.