The article examines the aspects of contention and conflict escalation before and during the period from November 2013 till February 2014 in Ukraine that have not yet received due attention in research. It studies the contention between the government and the opposition and the concomitant Maidan protest mobilizations by groups advocating unity with Russia, and opposing the visions of political community of the radical groups making up part of the Maidan coalition. Conflict escalation is studied as a combination of structural conditions, choices and actions taken by conflict agents, and evolving discursive factors that enable political violence. The analysis indicates that while structural conditions played a role, conflict escalation is a nonlinear and agency-driven process, evolving through mutually influencing choices and actions of the competing parties, that either drive escalation or lead to deradicalization. The article suggests that the modes of contention and radicalization between the government and the opposition opened opportunities for groups supporting unity with Russia to escalate their demands, to radicalize their visions of political community, and to build leverage with Russia. In conclusion, several key narratives and discursive processes enabling the legitimization of the use of force and the implications for peacebuilding are discussed. The findings help to understand better the environment in which violent conflict further escalated in 2014.