The South has never been a real space in the imaginations of authors from colonization-forward. From early works from the colonial era to the wave of Afrofuturist texts of the past several decades, the South has been a space of alternative realities, a site of speculation upon which authors projected imagined presents and futures. The “otherness” of the South has always lent the region a speculative bent in the United States and global imagination. This essay examines literature from the antebellum South itself, the supposedly geographically fixed monolith of plantation culture. Written by a majority white, proslavery authorship, southern imaginative writing before the Civil War always speculated on the “South” and shaped it as a cultural identity. To understand the endurance and widespread influence of the dominant versions of “South,” it is necessary to examine their literary origin point and not just the aftershocks and reverberations. Like writing about the South, writing from the South during the nineteenth century was always a speculative exercise, made especially evident when focusing on works by those invested in continuing an idea of “South” that lay the foundation for ideologies circulating long after the Emancipation Proclamation and the end of the Civil War.