Although Bayezid II seems to be much less than a glorious Sultan as opposed to military ambitions of his father and his son, it would be difficult to overstate the historical importance of his influence for the rise of Ottoman culture in the new capital of the empire. Trained in a wide range of disciplines, he was not only a poet who collected a divan (poetry collection) with the penname Adli, but also a generous patron who regularly supported more than 146 artists and scholars as opposed to his father Mehmed II’s 12, based on gift registeries and salary books. During his 31 years of reign, besides the abundant production of scholarship, literature and visual arts, Ottoman Turkish was established as the major medium for the literary culture and thanks to his master teacher Seyh Hamdullah, Istanbul was embellished with calligraphy in Ottoman style. Apart from his evident enthusiasm for arts and sciences, his personal life story registers the making of a statesman from being a bohemian Prince to a traditionally Islamic Sultan who is the major benefactor of his subjects. With the intention of mapping out the early modern culture production of the Ottoman empire, this paper traces the life of Bayezid as a man of letters in regard to his education and his relationship with his entourage such as Mueyyedzade and Kemalpasazade. The assumption is that an investigation and a comparative analysis of Bayezid’s literary history such as the poetry and/or calligraphy he produced, the people he chose to support as artists and scholars, the books he commissioned will show not only the networks behind the intellectual production but also the Ottoman artistic taste developed during this period, which has social, economic and political implications.