This chapter explores Jean Fouchard’s body of work on the history of culture and literacy in Saint-Domingue and its implications for the study of the long-term history of Haitian literature. Fouchard’s books, I argue, opened up portals into the worlds of Saint-Domingue that had previously been evoked in certain writings but not explored in the depth he offered: indigenous cultures and their continuing legacies, theatre, music, dance, and a constellation of handwritten texts produced by both enslaved and free people of African descent, and through these the broader cultural and intellectual visions and aspirations of these communities. Fouchard saw the history of writing, and literature, in Saint-Domingue as part of a deep and long process stretching from colonial times to the present day, and to identify continuities between different eras. Ultimately, Fouchard’s collective of work, which can be seen as all part of a larger overarching project, asks of us to see the cultural and literary history of his country holistically, as a connected and enduring series of struggles driven by a search for true expression, and therefore freedom.