The reign of Bayezid II (1481-1512) saw an unprecedented rise in the number of Ottoman jurist-scholars who compiled commentaries on the canonical works of post-classical legal theory and Hanafi substantive law. Scholars have posed many theories in the past decade to explain the function and purpose of legal theory and legal compendia in the regime of legal conformism. This paper probes into the question why post-classical jurists, who had no so much juristic leverage than browsing through accumulated jurist opinions within their madhhab repository, would pay much heed to cultivating the hermeneutical apparatus supplied by the works of legal theory. As a case study, I examine a sample of Ottoman juristic writing flourished in the late 15th/early 16th centuries under the patronage of Bayezid II. This juristic scholarship evinces an exclusive concentration on Ṣadr al-Sharī’a al-Maḥbūbī’s (d.1346) commentary on a compendium of Hanafi law, The Safeguard of the Transmission (Wiqāyat al-riwāyah fī masā’il al-Hidāyah) and his famous work on legal theory The Revision of the Methodology (al-Tanqīḥ al-Uṣūl). Scholarly entourage of Bayezid II nourished and cultivated a culture of scholastic disputation concentrated on formalistic aspects of legal and theological arguments in Ṣadr al-Sharī’a’s works, which had already engendered its chain of commentaries before the Ottoman jurists. Intellectual resources of the 16th century Ottoman juristic thinking had been invested in digging into the linguistic, rhetorical and argumentative capacities of these works, which indicates little concern with the alleged purposes of the post-classical legal writing, rule-discovery and rule-review. The Ottoman commentarial culture in the reign of Bayezid II culminated in Ottoman chief-jurisconsult Kemālpaşazāde’s (d.1534) ambitious and controversial project on a thorough “rectification” of Ṣadr al-Sharī’a’s aforementioned works. The titles of his works, Replacement of the Revision ( Taghyīr al-Tanqīḥ) and Revision of the Safeguard (Iṣlāḥ al-Wiqāya) give an indication of the polemic directed against the legal canon, on the grounds of the textual shortcomings of the tradition. In light of the recent scholarship on adab/Islamic paideia, I show the way this commentarial enterprise illustrates how the post-classical legal writing had been turned into a contested field, whereby Ottoman jurists vied for cogent elucidations of the legal problematics thanks to their competitive humanistic erudition.