The Ottoman historian Mustafa Naima (1655-1716) is distinguished among his peers for the popularity his writing enjoyed not only in his own lifetime but also throughout the later Ottoman era. His imperial chronicle, which covers the period from 1590 until 1660, has attracted scholarly attention for its historiographical sophistication, synthesis of a wide range of sources, and promotion of an agenda of state reform. Not surprisingly, scholarly studies of the Mustafa Naima have tended to concentrate on his career in Istanbul as a scribal official and official state historian (veka’i-nuvis). They place his education and cultural formation in the Ottoman capital and narrate his success in securing the patronage of high-ranking ministers. Relatively little attention has been paid to Naima’s social background, specifically his childhood and youth in the provincial city of Aleppo, and how that experience may have shaped his writing. This paper explores that world and draws attention to Naima’s deep connections to the military establishment of that city, especially the Janissary units settled there. This analysis relies not only on autobiographical narratives in Naima’s chronicle but also on new information on Naima’s family and social milieu found in the law court registers of Aleppo and in fiscal documents found in the Prime Ministry Archives. Naima begins his family history with his grandfather, a Janissary officer named Kuchuk ‘Ali Agha who settled in Aleppo in the early seventeenth century and established a prominent household. Woven into the grand narrative of Naima’s chronicle are multiple episodes that relate in telling detail the crucial intermediary functions of the Kuchuk ‘Ali Agha family and other localized Janissary officers in provincial political affairs, most notably in administering the powerful nomadic tribal confederations of the region. Tax survey documents and local court records reveal, among other things, an affluent family that produced the city’s Janissary commander (serdar), possessed several properties in prestigious quarters of both Aleppo and Istanbul, and owned slaves. While living most of his adult life as a scribe in Istanbul, Naima clearly had access to a rich store of family oral history and connections that informed his analyses of provincial affairs and made them relatively nuanced and balanced. His wide-ranging history was enabled by his social and cultural upbringing within a family that, in its intermediary functions between capital and countryside, transcended geographical and political boundaries.