Roman Osminkin (b. 1979) is one of the most prominent poetic voices from within the cultural opposition to Putin's political system. Osminkin's poetry employs two aesthetic and discursive models at the same time, each of which is politically charged. One of these models directly continues the legacy of Moscow conceptualism, and especially its leading poet and theorist Dmitrii Prigov (1940-2007). His other major influence comes from the Left Front of the Arts in the 1920s (LEF), which aimed to establish a new hegemony through a system of cultural practices. This chapter traces the interaction between these two discourses in Osminkin's poetry and some of his performative works. It then discusses the internal conflict characteristic of Osminkin's work, essential for a political discourse, which he defines as 'pessimistic enthusiasm' for the revolution, and which reflects more than just his personal position. Osminkin's poetry represents a faithful but highly creative variation on this rhetorical configuration typical of Russian postmodernism.