With the Ottoman conquest of the Mamluk Sultanate in 1516-17, the central Arab lands (Egypt and the Fertile Crescent), entered a new era in their history justifiably described as Early Modern. Scholarly study of the early Ottoman period (1516-1600) has shed light on the marked expansion of central state power, as demonstrated by urban development initiatives, comprehensive tax surveys of agricultural and commercial activity, judicial reform, and the building of infrastructure to facilitate trade and protect pilgrimage routes. The ways in which local Arab society and culture evolved under early Ottoman rule, however, remain greatly understudied. The noticeable decline, from the late Mamluk Sultanate period, in the production of local historical literature has discouraged historians from undertaking close study of this period. The present study seeks to make a micro-historical contribution to the study of early Ottoman-Arab society by examining the life and career of Ibrahim b. Khidr al-Qaramani (d. 1555), a wealthy, long-distance trader and architectural patron in the north Syrian city of Aleppo. Two sources have long been available for the study of al-Qaramani’s life and work, namely, the biographical dictionary of Ibn al-Hanbali (d. 1562), a contemporary Aleppan scholar and historian, and the socio-historical and architectural survey of Aleppo by another Aleppan, Kamal al-Ghazzi (d. 1933). In 2010 the present researcher discovered a third source, a trove of over thirty documents found in the earliest volumes of the Aleppo law court records, housed in the national archives of Syria. While Ibn al-Hanbali’s biography relates elements of al-Qaramani’s social reputation and public image, and al-Ghazzi his architectural vision and legacy, the court records disclose his strategies and methods as a businessman, and his patriarchal sway as father, husband, and slave owner. From these sources emerges some idea of the power, status, and worldview of merchants in early Ottoman Aleppo.