Published in 1853 as part of Julia Griffiths’ abolitionist gift-book and fundraiser Autographs for Freedom, the novella The Heroic Slave became canonized as Frederick Douglass’s sole and somewhat negligible attempt at sentimental fiction. The novella offers a speculative account of moments in the life of Madison Washington, one of the ring-leaders of the 1841 slave revolt aboard the brig Creole. The following essay proposes a rereading of The Heroic Slave in light of the historic events of the Creole incident and the subsequent tort lawsuit Thomas McCargo v. The New Orleans Insurance Company. I outline how Douglass’s novella taps into the probabilistic logic of the legal case and thus traces the lineage that historically connects slavery, risk, and marine insurance. My essay proposes a reconsideration of Douglass’s novella as an aesthetic experiment; it shows how The Heroic Slave employs elements of genre convention, narrative form, and symbolically charged spaces to present the reader with a case for self-empowered, African American agency, which hinges on a newly emergent probabilistic paradigm rather than providential convictions. A radical and deeply ambiguous text, the novella confronts the reader with the racial bias of historiography; it struggles to find a form that reflect slaves’ experiences of exposure to the seemingly aleatory uncertainties of the slave-keeping system, in which bodies became chattel and risks turned human futures into tradable commodities. Douglass’s text presents Madison Washington’s heroism not primarily as based on escape and violent revolt but on his voluntary and self-conscious act of seizing self-ownership and charge of his future. Thus, the novella bears witness to the inherently Janus-faced nature of risk, which indelibly ties its historic function as an economic tool of profitable slave trade to the liberating potential a probabilistic paradigm may hold for individual self-empowerment.