In censored discursive regimes, political jokes—despite their compressed linguistic and situational structure—transcend mere entertainment, operating at the threshold between articulation and silence. During the Glasnost era (1986–1991), the relative easing of discursive constraints transformed political humor into a vehicle for renegotiating power dynamics among the speaker, the hearer, and the ideological establishment. This study investigates the linguistic mechanisms through which political jokes generate and convey critical meaning indirectly, thereby immunizing the speaker against direct discursive accountability. The analytical framework synthesizes Grice’s Cooperative Principle and Conversational Implicature with Searle’s Speech Act Theory; van Dijk’s discourse-ideology framework is subsequently deployed at a macro-interpretive level to map micro-pragmatic findings onto representations of power. The corpus comprises twenty-eight political jokes from this period, selected from archival and scholarly sources based on five concurrent criteria (including temporal alignment with the Glasnost period, explicit political content, and documentation in peer-reviewed scholarship). A key limitation of the corpus lies in its reliance on jokes documented in English-language publications, with comparatively limited coverage of Russian-language scholarship. The findings indicate that the calculated flouting of the maxims of Quality and Relation generates conversational implicatures that convey critical force without explicit assertion. Speech acts within these jokes operate predominantly through indirect modes, creating a deliberate divergence between the surface (apparent) and the actual illocutionary forces, which shields the speaker from discursive liability. The sociopolitical context plays a constitutive role in triggering these implicatures; meaning is reconstructed solely through the dynamic interaction between the text and the interlocutors’ shared background knowledge of the prevailing ideological milieu. Notably, in select instances, the jokes simultaneously resist and reproduce certain dominant ideological presuppositions—a finding elaborated with empirical examples in the discussion. The primary contribution of this study lies in conceptualizing the political joke as empirical linguistic data rather than mere historical artifact, as well as systematically integrating these three theoretical traditions within a unified corpus—an integrative approach hitherto scarce in the existing literature.