This work examines the shaping of Ottoman intellectual life between 1302 and 1362 as part of the common cultural heritage of Turkistan, Iran, and Anatolia. The relevant Damascus-Cairo and Byzantine aspects are also considered. It will detail how the components of this heritage were transmitted to the Ottoman realm and investigate both the channels used and the institutions involved during the reigns of ʿOsman and Orhān Gāzī as well as the role of Dāwūd Kaysarī, who was considered to be the first Ottoman mudarris. The period’s political, intellectual, and ideological approaches will also be taken into account, and a brief context evaluation will be conducted on the al-Itḥāfu’s-Sulaymānī fi’l-ʿahdi’l-Ūrkhānī attributed to Kaysarī and presented to Sulayman Pasha. This scholarly work is identified as the first one to be compiled in the Ottoman realm. Its editio princeps will be appended to the article.