This article examines how Miskitu King Robert Charles Frederic (1824–42) used colonial contracts with foreign merchants to advance his political agenda in Moskitia, on Central America’s Caribbean coast. Drawing on European and Central American archives, this study challenges narratives that portray Indigenous leaders as passive actors in colonial expansion, highlighting how the king strategically wielded contracts to facilitate the import of foreign capital through concessions and loans. His mastery of international finance enabled resistance to imperial domination while allowing him to consolidate power, maintain independence, and participate in nineteenth-century Atlantic political transformations. However, this strategy compelled him to facilitate the entry of financial capitalism into Moskitia, subsequently defining his kingdom’s fiscal governance and external relations. By examining Robert Charles Frederic’s learning process in navigating Caribbean political and Atlantic financial systems, this article contributes to scholarship on Indigenous agency in colonial encounters and reveals how peripheral actors mediated the global spread of economic institutions.