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This essay explores the problematics of contemporary political performance through the plays of Guillermo Calderón. In particular, it seeks to account for the ways that Calderón’s theatrical aesthetics emerge from his negotiations with the material circumstances and institutional supports that condition his work. Tracing the history of the theatrical field and cultural policy in Chile, the essay examines the personal and structural pressures on Calderón and other Chilean artists to produce particular kinds of political artworks—pressures that contribute to a kind of political imperative. By reading Calderón’s dramaturgy both across his body of work and through the exemplary case of his 2015 play Mateluna, the essay explores the ways that dramaturgy emerges from negotiations with the political imperative. This analysis points to a processual and paradoxical dramaturgy, in which Calderón’s plays—driven by an ethical commitment to political resistance and responsive to the demands of an art market that positions political theatre as a saleable brand—re-problematize their political engagements with each new staging.