This chapter analyzes the transmedia strategies of opposition candidate Alexey Navalny’s campaign during the 2013 Moscow mayoral election. The goal is to highlight how the use of information and communication technology contributed to the development of democratic practices in Russia. His westernized, grassroots political campaign was a novelty in the country, involving online fundraising, door-to-door canvassing, engagement of volunteers, digital projects, and meetings with voters, for instance. The argument is that, although Navalny lost the election, his candidacy represented advancement in terms of both the use of new media and the promotion of democratic development in the midst of autocratic Russia. If the progress will be maintained, it remains to be seen. The theoretical framework includes the reality of the Russian political scenario and the conceptualization of transmedia storytelling strategies in the context of participatory politics. The methodological approach is based on the transmedia analytical model by Gambarato (2013).