In colonial environments, figures such as the interpreter, dragoman, fixer and ‘native informant’ are rarely viewed as radical. On the contrary, they are more likely to be viewed with suspicion, as ‘collaborators’ or at least unwitting facilitators of the colonial project, passing on knowledge that can be appropriated for nefarious purposes. By exploring these issues through examples from the period of British rule in Palestine (1920–1948), under a League of Nations Mandate, and considering the shifting and contingent place of power in their workings, this chapter considers how such roles might be understood as activist. Going beyond the sometimes uncritical perceptions of cross-cultural contact as inherently generating closeness and understanding, rather than as resistant or assertive, it instead suggests that in the activities of individuals such as Haddad, Docmac and Baydas, who negotiated many paths through colonial institutions and systems of knowledge. This chapter foregrounds the ability of the translator, amid even the most complex of colonial systems, to question, disrupt and fragment conventionally political understandings of power in society.