This paper examines the political economy of the Orange Revolution in an effort to understand routes by which less democratic postcommunist countries might break with an illiberal status quo. The fusion of Ukraine's rent-seeking economic interests and illiberal political regime produced an unstable equilibrium that is poorly explained by two leading theoretical frameworks: ‘market reform’ and ‘political competition’ theory. Only by combining key insights from each do we get a full explanation of the pressures that generated Ukraine's challenge to illiberalism in 2004. We examine this story with a particular focus on the crisis-prone nature of ‘competitive authoritarian regimes’ and the related strategic calculations of business elites.