Iosif Volotskii’s practical and rhetorical mastery of logic was a major factor in its pedagogical and polemical effectiveness. This logic pervades his Prosvetitel’ (Book against the Novgorod Heretics) in the structure of each discourse, grouping of the discourses, ordering of subjects and themes within and among the discourses, hypothetical heretical objections and Orthodox refutations, sequencing of proof texts, application of syllogistic literary devices, explicit epistemological principles, emphasis on and variety of proofs, enthymematic presentation of both the major heretical doctrines and the Orthodox correctives, and overall syllogistic interconnectedness. The numerous formal refutations in Discourse 11 partially explains its division into four chapters, while the greater unity of discourse structure of the theological Discourses 1–11, in contrast to the more prosecutorial Discourses 12–16, speaks in favor of the chronological primacy of the brief redaction. The positive theology and ethics are presented as a coherent whole, as is the binary opposition of legitimate ruler, pastor or pious layman vs. the tyrant, “wolf,” or lay heretic. The reliability of Prosvetitel’ as a source for dissidence remains questionable, but its pedagogical utility for Orthodox Muscovites is indisputable.