Alternate histories about the American Civil War seem ideally set up to explore the possibilities and tensions of social criticism through art and literature. Counterfactual stories about the war easily invoke contemporary issues of inequality and exploitation, and they are part of a genre—alternate history—that has traditionally lent itself to social commentary. Yet while scholarship on alternate history has captured the presentist orientation of many alternate histories in the fantasy-nightmare dichotomy, these categories appear reductive as a reflection of the layered and intriguing forms social criticism takes in Civil War alternate history. This article examines two examples of this genre that position themselves as political statements. Frank Purdy Williams’s largely forgotten novel Hallie Marshall: A True Daughter of the South (1900) subverts major literary traditions of its time to mount a counterintuitive critique of capitalist exploitation. Kevin Willmott’s mockumentary C.S.A.: The Confederate States of America (2004) is both a scathing critique of American racism and a multilayered satire on the distortion of history in popular culture. Both works use the conventions of alternate history as conduits for critique and provocation, which makes the revelation of their ideological investments ingenious but perhaps dangerously circuitous.