The article studies a complex of little known historical processes in Southwestern Maluku and East Timor in the late 17th century. These occurred in the intersection between early colonial attempts at political and economic control, and local strategies to either accommodate or avoid such control. The article argues that the aspirations of European or Eurasian groups - the Dutch VOC and the ethnically mixed Portuguese Topasses - allowed certain local leaders to use early colonial rivalries to build up positions that transgressed their customary prerogatives. Moreover, the processes must be seen as an interplay between global, regional and local spatial levels. The article focuses in particular on two protagonists. Bakker, a chief in the island of Kisar, was briefly expelled through a Topass invasion in 1668 but reinstated by a Dutch expeditionary force, henceforth cooperating closely with the Dutch post in Banda. Sili Saba (Raja Salomon), was the ruler of Ade (Vemasse) in East Timor. An attempt to ally with the VOC in 1668 misfired as the Topasses invaded East Timor in the same year, and Sili Saba was installed as interlocutor for the VOC in Wetar. The article shows how the Wetar Straits, which had a binding function for culturally similar populations, was turned into a sea border which still persists. It also demonstrates how local groups obstructed the imposed order through resistance and migrations.