This study investigates the status of poets and poetry in sixteenth-century Ottoman Damascus by focusing on soldier-turned-poet Māmayya al-Rūmī (d. 985-7/1577-9). As a poet he received patronage from local centers of prestige; however, such support seems to have been at best sporadic. While his dīwān (collection of poetry) is replete with poems celebrating his poetic ingenuity—notwithstanding the fact that he was not a native Arab, it is also a testimony to his frustrations with lack of financial security and his diminishing social status. In addition to gloomy poetry, he also composed a great number of panegyrics in honor of Ottoman sultans, scholars, and administrators. What was Māmayya’s position in the literary culture of sixteenth-century Damascus as a Rūmī? What was the role of panegyric poetry in this period? Did poets voice their concerns about lack of appreciation? This study explores these questions by focusing on a selection of poems by Māmayya al-Rūmī with references to his contemporary, and later poets.