The article explores the common Southeast Asian epistemological theme of a “stranger king” as an ordering principle in a polity, a principle that was also relevant in a colonial context. The case studied here is the Dutch colonial post in Kupang, West Timor, in the VOC period, 1653-1800. The Dutch fort was surrounded by five princedoms, which stood in the relation of subordinate allies to the VOC. Four of the five groups had migrated to Kupang due to pressure from the Portuguese and their clients, which dominated the rest of Timor. Arenas of interaction were developed, whereby the elites of the five princedoms deliberated with the Dutch authorities on a regular basis. Their attachment to the Dutch colonial apparatus was actually never broken until the twentieth century, in spite of several reasons for discontent. The article argues that the peculiar situation on Timor, where the five allies were under siege from the clients of the Portuguese, underpinned a system in which the colonial masters were seen as legitimate “princes”, ultimate referents of authority whose very strange-ness enabled them to hold the system in place.