This paper analyses the cases of penal prosecution of the symbolic and performative forms of dissent carried out by politically-motivated artists and activists in contemporary Russia. It posits the legal battles expanding around these cases against the backdrop of post-Soviet state transformation resulting in an authoritarian turn, and presents them as eloquent examples of productive convergence between the artistic and the juridical fields, the latter represented by politically-motivated lawyers, following the cases pro bono. This process shows three things: first, how newly forged legal concepts and categories that bear a punitive function (such categories as hooliganstvo, or razhiganiye rozni) are interrogated and tested by visual artists, public intellectuals and activists; and second, how the judiciary system, and especially the prosecution, the courts, and the defence, respond to these challenges with a set of available juridical tools--that are sometimes developed ad hoc.Unlike other research dedicated to political dissent in Russia, my investigation, carried out in 2015-2017 in Saint-Petersburg and Kazan, revealed the existence of effective strategies of defense of political cases in Russian criminal courts. These strategies are developed and implemented collectively on both domestic and international level the Russian “cause lawyers”--a socio-professional group, that has not yet been comprehensively described in the socio-legal literature. This research presents an analysis of the intellectual, strategic and symbolic exchanges between two groups of committed social actors and deals more generally with the recent fundamental ideological transformations of the post-Soviet legality and the subsequent reconfiguration of the legal profession.