“Brokering Literacies” is a study of how English acquisition can transform family relations in a specific Latino urban immigrant community. My research examined the effects of English literacy on family structures within ten first-generation Mexican American families participating in an after-school mentoring program in New York City. Through ethnographic observation and discourse analysis, I analyze social relations in the bilingual exchanges among related individuals in this community setting. For these families, becoming bilingual and accumulating linguistic capital had complex unintended impacts on their relationships. Acquisition by some family members of high-value cultural capital thus secured an asset that re-wrote traditional family relations, which consequently affected family attitudes toward schooling. Paying particular attention to the interactions between parents and children, this research investigates how power relations between English and Spanish literacy fluctuated, especially for dependent children who gained the upper-hand in English. This acculturation was identified as a point of intervention for educational support and community building for the grassroots mentoring program.