The article deals with the development in Russian-Estonian relations during the crises of 2007 and 2014, taking into consideration the balance between political and economic factors in the decision-making by Estonian government. A number of special aspects, trends and problems in trade and investment ties are detected. The aim of the study is to uncover key motivation behind the actions of both Russia and Estonia, to identify the drivers for economic and political development in the region, and to work out recommendations to adjust them. The questions put forward by the authors of this article could not be more topical at the time, when Russian economic situation is obviously getting worse and capital flight (to the neighboring EU Member States) is likely to increase. The method of the study is comparative analysis of the impact on economic ties made by Russian-Estonian crisis of 2007 and the current international tension around Ukraine. The regional fossil fuel market and the possibilities of Gazprom involvement in its development are also analyzed. It is concluded that political motives are still important for Estonian decisionmaking, though they are balanced out by measures of business support (despite some of these measures being taken by the EU bodies). The role of political factor for the Russian side is increasing. It is acknowledged that there is a growing number of missed economic opportunities in the Russian Northwest.