The figure of the dragoman, interpreter and intermediary between linguistic, diplomatic, and religious worlds, emerges in this monograph as a central figure in the daily and institutional life of the Custody of the Holy Land during the Ottoman period. Through the publication and commentary of an unpublished documentary corpus – twenty records of the Sharia court of Jerusalem (1561-1671) and three accounting documents from the monastery of St. Saviour (1711-1773) – the author recovers the profile of these figures not only as interpreters, but also as legal mediators, economic administrators, and protagonists of the complex social and linguistic fabric of Ottoman Jerusalem. This book has been funded by the European Research Council (ERC) under the European Union’s Horizon 2020 Research and Innovation programme (Grant Agreement 101001857) as part of the project ‘HOLYLAB – A global economic organization in the early modern period: The Custody of the Holy Land through its account books (1600–1800)’.