This thesis examines the variation of political and economic outcomes in the post-communist countries of Eastern Europe. In my evaluation of these outcomes, I find that path dependency is a major determinant of post-communist divergence. This divergencecan be traced back as early as the communist era itself, in which differences amongregimes including leadership style and strength of civil society later impacted the qualityof collapse and transition. I compare the democratic and developmental trajectories of Poland, Slovakia, and Romania in order to trace the influence of path dependency anddemonstrate how varying starting conditions led to different outcomes. A comparativestudy of these cases suggests that more successful outcomes resulted from countries withrelatively more liberal communist regimes with rational approaches to rule and greater opportunities for civic engagement. On the other hand, countries with repressivecommunist regimes led to poorer outcomes. Put simply, post-communist countries as theyare today reflect a progression of events that originated within the communist perioditself.