Critical scholarship on migrant brokers and brokerage have problematized the popular dichotomy of brokers as either altruistic or exploitative. Current research seeks instead to understand the diverse relationships and power dynamics between such migration intermediaries and migrants, and the strategies that both parties employ to reduce the risks inherent in long-distance international migration journeys. Drawing from a broader ethnographic project on Southeast Asian migration to Chile, this article presents the narratives of two Filipina women who facilitated the migration of Filipina domestic workers to Chile. Analysis of their experiences contributes to problematizing the category of “broker” and to understanding the complex and gendered dynamics of care and control that some intermediaries establish with migrants. I emphasize how these brokers’ gendered migrant subjectivities shape their processes and strategies of mediation. In the specific context of Southeast Asian migration, focusing on these intermediaries sheds light on more individualized forms of migrant brokerage, in contrast to the predominant research on migration policies and commercial migrant recruitment and placement agencies. Attending to the complexity of who “brokers” are and their roles is important in apprehending migration and border policies that depend on defining their roles in the migration process.