This paper explores the tensions within Shafi‘ism in Ayyubid Damascus by examining the relationship between its two leading authorities in the first half of the thirteenth century, Taqi al-Din b. al-Salah (d. 643/1245) and ‘Izz al-Din b. ‘Abd al-Salam (d. 660/1262). The nascent Shafi'i community in Damascus evolved from the Shafi'i traditions of Khorasan and Iraq that preceded it, which had developed autonomously throughout the fourth/tenth and fifth/eleventh centuries. These two regional traditions were ultimately fused into a single authoritarian school doctrine by Mamluk era jurists, most notably al-Nawawi. Prior to this however, the Ayyubid period formed an intermezzo of sorts for Shafi'ism, where juristic proponents of the two until then insulated regional traditions converged upon Damascus, where they clashed over crucial issues of methodology. The legal history of Shafi'ism during both its Khorasani-Iraqi phase and after its transplantation into Ayyubid Damascus have received little scholarly attention, giving us only a vague understanding of the conceptual-historical categories of the Khorasani and Iraqi interpretive traditions (turuq) of the Shafi'i school and the subsequently painstaking process of synthesizing the two streams. In this paper I utilize the rivalry between Ibn al-Salah and Ibn ‘Abd al-Salam as a window into these larger competing trends within Shafi‘ism as it evolved from its Khorasani and Iraqi legacies. I first situate Ibn al-Salah and Ibn ‘Abd al-Salam within distinct intellectual genealogies and networks in Damascus. Ibn ‘Abd al-Salam was embedded in the more analytical and speculative Khorasani interpretive community, while Ibn al-Salah inherited the conservative and transmission-based orientation of the Iraqi tradition. While formal attribution to the Khorasani and Iraqi lines of the school gradually ceased with the destruction of Khorasan, the intellectual legacies and distinct methodologies of each stream vied in Ayyubid Damascus, with Ibn al-Salah and Ibn ‘Abd al-Salam being outstanding representatives of these contending approaches. Through a reconstruction of their biographies and close reading of their largely unexamined writings, fatwas and counter-fatwas, I show how their recurrent clashes epitomized these long-standing fault lines within Shafi'ism. At stake was first the validity of dialectic theology and its influence on other sciences like legal methodology, which Ibn 'Abd al-Salam supported while Ibn al-Salah vehemently censured. Also at issue was the legitimacy of legal innovation and embracing unprecedented opinions in the tradition of ijtihad, which Ibn 'Abd al-Salam engaged in without hesitation while Ibn al-Salah’s conservative orientation kept him in close adherence to existing school doctrine.