||The future tends to be determined by the legacies of the past. The transition of the eastern European countries, from abolishing Communism to adopting Democracy, suggests just that. These countries bared traits of their previous un-democratic regimes that have contributed to the democratization process. The relevance of this statement will be analyzed throughout this study, by looking at two specific cases from Eastern Europe which are characterized as successful democratic transitions, namely Poland and the Czech Republic. Despite the relatively similar international and domestic state of affairs prior to the dissolution of the Soviet Union, the newly emerged regimes took different trajectories towards the implementation of democracy. This raises the discussion on the causal variables behind the rather distinctive paths towards democratization, which is argued here to be attributed to the historical legacies of the countries.