Ayuba Suleiman Diallo’s 1731 journey from a trader of enslaved people, to enslaved, and back a trader of enslaved people is both remarkable and seemingly contradictory. However, his involvement in the West African trading networks bridged the goods-centered market and the ensuing one centered around enslaved people. Thus, his actions reflect the economic insecurity that permeated Senegambia, and his return to trading enslaved people illustrates the need for a competitive edge in these newmarkets. Foundational to his return were his manipulation of race, color, and religion in response to an increasing demand for enslaved people. Diallo established himself as different than the enslaved people around him, positing that he was instead more similar to his white captors. Through his royal mannerisms and devout practice of Islam, Diallo befriended Thomas Bluett, James Oglethorpe, the Duke of Montagu, and even King George II and Queen Caroline. He was branded “the Fortunate Slave” and frequently described as a white man with black skin. Diallo’s actions allowed him to regain enough social capital to travel to England and eventually return home to Bondu in present-day Senegal. Once home, he participated in the trade of enslaved people far more zealously than before his capture, which emphasizes how the Senegambian markets had transitioned away from being goods-centered during his absence in response to British demand. Diallo’s story illustrates the changing nature of Trans-Atlantic slave trade as well as eighteenth-century attitudes towards race and slavery.