Between the late sixteenth and mid-eighteenth centuries, black eunuchs rose to unprecedented prominence in the political structures of the Ottoman Empire. While this rise to power has finally drawn the attention it deserves in Jane Hathaway’s The Chief Eunuch of the Ottoman Harem (2018), the literary sources that reflect the complicated relationship between gender, race, slavery, and political power surrounding the African eunuchs await further study. The sources I would like to focus on in this presentation are two Ottoman treatises written in the early seventeenth century and presented to the chief black eunuch of the time: The Mirror for Ethiopians by Ali Khabi (d. 1612) and Dispelling the Darkness by Mullah Ali (d. 1623). While arguably different from modern racism, pre-modern Middle Eastern written cultural products nevertheless display undeniable prejudices against Africans. Ali Khabi and Mullah Ali turned these prejudices upside down, giving African slaves a proud place in Islamic history by associating them with the Ethiopian Negus who was a contemporary of Muhammad and protected the Muslim refugees who sought asylum in his kingdom. Thus, whether or not an African slave was actually from Ethiopia or had been a Muslim before enslavement, once he was called Ethiopian, he was associated with a pedigree that went back to the time of Muhammad. The difference in the approaches taken toward the connection between race and slavery in the writings of Ali Khabi, a Turkish jurist from Bursa, and Mullah Ali, who was a former African slave presented to a former chief black eunuch as a gift, is very striking and opens a window to the alternative meanings of blackness, too. While blackness could be associated with slavery as evidenced by Ali Khabi, this association could also be refuted as displayed by Mullah Ali. What is perhaps most striking and what will be the main focus of this presentation, however, is the place of pride given to eunuchs in the Prophetic traditions narrated by Mullah Ali in the several chapters he devotes to eunuchs in his Dispelling the Darkness, associating the term servant specifically with eunuchs already during the lifetime of Muhammad. Eunuchs, with the assumed fluidity of their gender, were the only men who were allowed access to both the sultan and the royal women, and the patronage dispersed by all of them. This particular positioning made these emasculated men more powerful than most in the early modern Ottoman period.