This dissertation studies organized charity work as it was performed in Boston, Philadelphia, New York, Charleston, and Kingston, Jamaica from the last decade of the eighteenth century to the middle of the nineteenth century. I study the writings of Charles Brockden Brown, Richard Allen and Absalom Jones, Sarah Pogson Smith, Nancy Prince, and Sarah Josepha Hale alongside other primary and secondary texts to show the mutually sustaining bond between benevolence and other forms of capitalistic labor of this period, particularly literary production. I argue that charity work functioned during the late-eighteenth and nineteenth centuries as an innovative and profitable form of labor that allowed marginalized individuals to contravene the strictures surrounding race, gender, and class that determined a laborer's earning potential within the American workforce. My research closely analyzes a variety of literary and historical sources to demonstrate that women, people of color, the disabled, and other disenfranchised groups carefully positioned themselves along circuits of exchange in a global economy because they recognized that charity was not a hobby but a business, successful only to the extent that it adapted itself to viable economic models and responded rapidly to shifts in larger market trends