The aim of this study is to investigate differences that exist in Estonia and Russia with regard to civil society, democracy and corruption and try to find out what can be possible causes to the vast differences in these two countries. Many political scientists claim that civil society plays a key role in democratic transitions. This paper takes its point of departure in 1991, when the Soviet Union collapsed and Estonia and Russia became independent. Since then Estonia has had a flourishing economy which attract many foreign investments, with Sweden as the greatest investor. The country has also managed well to adjust quickly from totalitarianism to democracy. This paper also addresses issues with corruption as it is a major problem in Russia and affects every day life in society. My results show that since Vladimir Putin came to power, Russia has got a higher degree of corruption and the evolution of democracy has gone backwards. I also found that there is a lack of social capital in the Russian society. In Estonia however, the results show that the country now has a well-functioning democracy. The legal environment for NGOs has steadily improved since Estonia became member of the EU. However, there still remain some deficit with regards to being a participating democracy at the grass-root level within the civil society. The theories used in this paper are Heidenheimer´s theory on corruption and Robert Putnam´s institutional theory on horizontal organization and social capital. The methods used are comparative case study and most similar systems design.