In the century following his death in 638/1240 the legacy of Ibn al-'Arabi spread throughout the Muslim world attracting both dedicated followers and also sharp critics. According to an early Ottoman narrative Sultan Orhan assigned the medrese he built in Iznik, traditionally regarded as the first medrese of the Ottoman Empire, to Davud-i Kayseri, a scholar known to represent the intellectual tradition of Ibn al-'Arabi. This narrative has received considerable interest in modern literature both on the cultural and religious history of the Ottoman Empire and on the dissemination of the legacy of Ibn al-'Arabi in the Muslim world. However, a critical reading of the modern literature reveals that neither the circumstances nor the implications of this assignment have been explicitly identified. In fact no extensive research has been undertaken to discuss the Ottoman sources on this matter. In this paper I provide an overview of the Ottoman legal and literary sources on the assignment of the Iznik Medrese to Davud-i Kayseri by Sultan Orhan and point out certain problems these sources present in understanding the factors that might have been effective in this delegation and the extent of the role Davud-i Kayseri played in the local dissemination of the Ibn al-'Arabi school of thought. I first discuss the surviving abridged version of the vakfiyye of the Iznik Medrese which contains only a summary version of the original. Here I bring to attention the problem this summary version of the vakfiyye poses for identifying the director (mutevelli) of the Iznik Medrese described therein specifically as Davud-i Kayseri, the commentator of the Fusus of Ibn al-'Arabi. Secondly I survey the Ottoman chronicles and biographical dictionaries where this assignment is mentioned. Here I specifically discuss the history of Asikpasazade which is the first Ottoman literary source to convey this narration and bring to attention the indications that suggest his source for this particular piece of information might as well have been his contemporaries rather than an eye-witness account of the reign of Sultan Orhan through the work of Yakshi Fakih. This study constitutes an initial effort towards a much needed evaluation of the political, social and cultural circumstances and implications of Davud-i Kayseri's presence in early Ottoman Iznik as a representative of the intellectual legacy of Ibn al-'Arabi.