Abstract According to an anecdote in al-Tanūkhī’s Nishwār al-Muḥāḍara, a merchant by the name of Ibn Abī ʿAwf (d.297/910) realized every capitalist’s fantasy: he monopolized the market for olive oil in the Abbasid capital of Baghdad, and manipulated market prices for immense personal profit. By examining a series of related anecdotes, this article poses several questions regarding Baghdadi society: What was Ibn Abī ʿAwf’s background? What was the source of his capital, and what social relations did he develop in order to become a prominent merchant? What financial tools were available to him in his mercantile activity? What social norms governed the pursuit of profit? And what sources can we mine for analyzing such socio-economic norms? We will see that the financial world of third/ninth century Baghdad had a variety of tools for debt financing; that an ambitious merchant needed to maneuver a complex web of relationships in order to succeed; and that contemporary sources reflect an ambivalent attitude — a grudging appreciation but also discomfort — with the pursuit of profit.