This paper is an unofficial overview of constitutional development of Czechoslovakia, key historical events, and points which I personally consider critical in its democratic development. This book does not represent point of view of any official authority. It is my personal attempt to get straight the events and their meaning, to the best of my current understanding and ability. Transition of Eastern European countries from Communism to democracy has not been painless and without affairs. Twenty years from abolition of one Party rule, it is time for a serious reflection of what has been accomplished, and where are the most serious areas of concern. Communist Czechoslovakia, after the Velvet Revolution (1989) and the breaking off Slovakia (1992), was transformed into a country with multiparty democracy with proportional representation in two-chamber Parliament; became a member of NATO (1999) and the European Union (2004); and its economy compared to other European countries is doing reasonably well. As most other small players, the Czech Republic seldom appears on international political scene with anything of significance. This paper discusses history of Czechoslovakia in international context, and presents some not widely known international agreements signed by the exile government of Edvard Bene . Czechoslovakia during its short history became part of two authoritarian empires, first as Protectorate of Nazi Germany and second as a Soviet satellite; and its road to democracy was littered by hundreds of thousands of bodies of civilians slaughtered at time of peace. This text was inspired by Robert A Dahl's paper "What institutions does large scale democracy require?" which was published in PSQ, Vol. 120, No 2; summer 2005. The first section briefly presents constitutional development of Czechoslovakia from the end of WW1 until 1992, and explains the most important changes introduced by the respective governments. Analytical part of this section takes the conditions of poly-archal democracy as explained in Dahl's paper and applies his conclusions to the situation in Czechoslovakia. The purpose of this paper is to try to identify the main reasons why the "project Czechoslovakia" went so terribly wrong. Second section presents observations of critical incidents in the history of Czechoslovakia. This overview is very brief and emphasizes only incidents which I personally consider key turning points. Sections three and four are dedicated to identification of possible design flaws in the electoral system itself, namely when it comes to its substantive meaning; and to the power of media in a closed society seriously constrained by language barrier. The fifth, concluding part, compares my observations to the Dahl's principles of poly-archal democracy, and defines conditions which can potentially prove critical for further democratic development. The system can have many formal characteristics of democracy, and be in fact a ruthless authoritarian regime with high level of democide. The paper is meant to contribute to the discussion what is the difference between democratic and authoritarian regimes, and to help identify conditions which directly lead to tyranny. The Appendix contains two long forgotten bilateral agreements between Czechoslovakia and USSR from World War Two, substantive excerpt from the Ko ice Government Program, and analysis "Background to Czechoslovak crisis" by former U.S. Ambassador to Czechoslovakia Laurence A Steinhardt."