This article argues that Ralph Ellison in Three Days Before the Shooting... radicalizes John Dewey’s pragmatic philosophy. To that end, the character arc of the black jazzman LeeWillie Minifees, who sets his expensive Cadillac aflame in the public sphere, discloses a dormant revolutionary zeal in Ellison’s political imagination. The two narrative spaces Minifees occupies—chapters four and fifteen—articulate a scathing critique of late capitalism and its attendant effect on US democracy. This article therefore posits that Minifees’s Cadillac-burning dissent constitutes a mode of creative democratic experimentation that is typical of the Deweyan pragmatic tradition, except that the jazzman’s actions suggest that the unmaking of the extant material conditions of existence is a precondition for African American subjects’ acquisition of proper political agency. In light of the analysis conducted herein, this article concludes that Minifees’s character arc should occasion a reassessment of Ellison’s textual politics, which are too often reduced to the thesis that black and white US citizens cannot escape their shared histories.