Democratisation and consolidation of a political system encompass a range of complex challenges, for which effective leadership is pivotal. However, the skills that a leader requires to break through and introduce change are not necessarily the same as those needed to maintain stability. This article examines the case of Viktor Yushchenko as president of Ukraine following the Orange Revolution. The negotiated transfer of power from the previous semi-authoritarian regime rendered consolidation difficult by limiting opportunities for a complete break. Within the residual 'grey area', a number of actors continued to participate and create tension. The regime that emerged was characterised by political infighting and instability, leading to the defeat of candidates associated with the Orange Revolution in the 2010 presidential elections. This article argues that the inability to move towards a consolidated democratic political system was due to the failure of the transitional leader, rather than the political and institutional configuration.