This paper focuses on the question of transformation of the Orthodox tradition in the postmodern context. The apophatic theology and the institute of Holy Fools (jurodstvo) are the most hermeneutic and mystical parts of Byzantine and Russian Orthodox cultures. These practices are now detached from their original sacral context and are used as rhetorical devices. The process and the results of such transgression are studied on the examples from the works of Dmitry Prigov and Vladimir Sorokin. In this paper I concentrate on three rhetorical figures that are used by these authors: logogriph, amplification and ostranenie.