Scholars have recently argued that New Netherland should be studied as an integral part of the Atlantic World. One important aspect that has been largely neglected in this wider geographical approach is that of Dutch interactions with native peoples. This dissertation addresses this issue by comparing Dutch-Indian relations in New Netherland and Dutch Brazil. I use intercultural mediators as a tool to analyze Dutch-native relations in the two Dutch American colonies. Because mediators frequently crossed cultural boundaries as interpreters, diplomats, and negotiators, they are fascinating characters for scholars studying interactions between Indians and colonists.  In comparing mediators in New Netherland with those in Dutch Brazil, this dissertation demonstrates that local contexts played an important role in shaping cross-cultural interactions in each colony. In Brazil, the Dutch struggle against Portuguese colonists primarily determined Dutch-Indian relations. Both the Dutch West India Company and the various Tupi and Tarairiu peoples of northeastern Brazil needed each other as allies against the Portuguese. In New Netherland the situation was different because there was less fear of a European enemy until the rise of English aggression in the 1650s. In contrast to Brazil, Indians and colonists in New Netherland were brought in close and frequent contact by an informal frontier exchange economy. Despite their different responses to the Dutch, the native peoples in Brazil and New Netherland shared the goal of maintaining independence from their Dutch allies and trading partners.  My comparative analysis also complicates commonly held views of Dutch attitudes toward Native Americans. Contrary to traditional assertions that depict the Dutch as solely driven by material exchange, this dissertation shows that Dutch-native interactions in the Atlantic world were also shaped by religious and imperial motives. Finally, this study of mediators in two different colonies demonstrates that the go-betweens did not bring the Indians and Dutch colonists closer together. Although Dutch and Indian negotiators often crossed cultural boundaries to maintain alliances or to prevent bloodshed, they did not create a middle ground of shared symbols and practices. By taking a comparative perspective this dissertation reveals the complexities of Dutch-Indian relations in the Atlantic world.