Tracing the relationship between the African American poet James David Corrothers and the influential political theorist Henry Demarest Lloyd, this chapter provides an example of interracial patronage that nuances our sense of black-white relations in late-nineteenth-century Chicago. As a man of means and a leading progressive activist, Lloyd supplied Corrothers with both financial support and also access to the emerging world of social reform. His impact on Corrothers’s political views is traced through the younger man’s letters to Lloyd in which he addresses the “free silver” debate, labor conflicts, African emigration, and the “Negro Problem” broadly. Moreover, the correspondence reveals the challenges confronting Corrothers as he struggled to launch a writing career while earning a living in a city offering limited employment opportunities for blacks.