Taqī al-Dīn al-Subkī (683–756/1284–1355) and Taqī al-Dīn Ibn Taymīyah (661–728/1263–1328) were two prominent scholars that shared a name, a time period, and a geographic locale. They were, however, anything but colleagues: al-Subkī embodied the Cairo Sultanate’s administrative normativity; a chief judge and the father of a chief judge, al-Subkī stood in stark contrast to the oft-dissenting Ibn Taymīyah, the latter being no stranger to the Sultanate’s jail cells. The two scholars also diverged legally on many points: al-Subkī’s biography is replete with mentions of polemics against Ibn Taymīyah and vice versa. Despite their famous differences on points ranging from the eternality of hellfire to the legal status of oaths of divorce, the two men had a shared position on muzāraʿah, the sharecropping contract. The Hanbali Ibn Taymīyah concurred with his madhhab’s position on the topic, offering a new rationale to the classical position. The Shafiʿi al-Subkī, in contrast, admits that by adopting the opinion he articulates on sharecropping, he dissents with the dominant position of the madhhab, including the opinion of its revered eponymous scholar, Muḥammad ibn Idrīs al-Shāfiʿī (d. 820). This study explores the ways the two scholars dealt with this legal question and uses the question of sharecropping to better understand how scholars dissented or concurred with their madhhabs based on both legal and extra-legal factors.