So far, modern historiography has constructed the relationship between the Ottomans and the Mamluks through the lens of wars and conflicts. Yet this relationship went beyond a mere military conflict. In fact, it presents a neglected phase of Ottoman identity formation. The concomitant existence of two leading Sunni Muslim powers not only offered the people living in these territories new opportunities, but also led them to question their allegiances. That both Ottoman and Mamluk ruling classes primarily spoke Turkish further complicated the situation. A so-far unstudied Ottoman prisoner’s letter sent from a Mamluk prison in 1486 suggests that the existence of Sunni Muslim and Turkish-speaking Mamluk sultans, whose legitimacy was solidly based upon their roles as the protectors of Holy Shrines, shaped the manner by which the Ottoman sovereigns presented themselves to the audience in Mamluk lands, particularly during the decades between the 1480s and 1512 – a period when the Ottoman administration was particularly invested in the formulation of an imperial identity. In the meantime, the careers of two fifteenth-century prominent scholars, Molla Gürani and Molla Arab, who never severed their previous ties with Mamluk institutions and regime despite building successful careers in Ottoman learning institutions and legal system, yields unexpected insights about the dilemmas of the people caught between two loyalties and about the continuing strength of the Mamluk regime’s image in the Ottoman territories. These individuals not only served as agents of Mamluk influence in Ottoman lands, but also contested the newly formulated claims of superiority vis-à-vis the Mamluk sultans. The evidence suggests that despite the remarkable Ottoman growth and territorial expansion it was not easy for the Ottomans to counter the Mamluk legitimacy and ideological superiority.