The article ponders upon background and outcomes of development strategies chosen by post-Socialist states within the last 25 years, the fundamental limits and opportunities of choices, and evaluation of their progress scaled between traditions and modernity. The problem of development in the former ‘second world’ is being analysed from the viewpoint of, if to generalize, contemporary institutionalist theories in political economy, namely the approaches by Douglas North, Hernando De Soto and the Austrian School, particularly with attention to Joseph Shumpeter’s concept of creative destruction. The political process in the region is colligated through the works of leading Russian political scientists, economists and sociologists.