This paper investigates the role that Dicky Barrett played as interpreter for the New Zealand Company from 1839 to 1840. Barrett was instrumented in the Company’s purchase of vast areas of land. Within a short time, however, it became apparent that the Maori and the Europeans participating in the sales had different perceptions of what had taken place. The legality of the transactions and Barrett’s role as mediator between Pakeha and Maori were questioned in the Land Court three years later. The court records and diary entries of Dicky Barrett’s contemporaries and superiors shed some light on how Barrett himself understood his role and how he acted as an interpreter, working at the faultline of cultural understanding, in the service of the New Zealand Company.