Toussaint Louverture, hero of the Haitian Revolution, occupies a key space in the imagination of Black masculinity across his own time up through the present day.This chapter traces the way Toussaint Louverture’s body, in particular, is reimagined and represented both as a symbol for Black heroism and, taken together as an oeuvre, as a figure that undoes this masculine paradigm of Black politics. In texts as varied as C. L. R. James’s, The Black Jacobins, Toussaint L’Ouverture, Édouard Glissant’s Monsieur Toussaint, and Ntozake Shange’s For Colored Girls, as well as visual art, cinema, public monuments, performances, children’s books, and his own memoir, Louverture’s body reads across various times, spaces, and forms as a site of desire, vulnerability, and contested lineage for Black masculine “freedom dreams.” His continued embodied celebrity is more complex than an individual text’s objectification, and instead acts as a recurring scenario of Black political negotiation across key historical moments.