This book explores the humanities as an insightful platform for understanding and responding to the military prison at Guantánamo Bay, other manifestations of “Guantánamo,” and the contested place of freedom in American Empire. It presents the work of scholars and writers based in Cuba’s Guantánamo Province and various parts of the US. Its essays, short stories, poetry, and other texts engage the far-reaching meaning and significance of Gitmo by bringing together what happens on the U.S. side of the fence—or “la cerca,” as it is called in Cuba—with perspectives from the outside world. Chapters include critiques of artistic renderings of the Guantánamo region; historical narratives contemplating the significance of freedom; analyses of the ways the base and region inform the Cuban imaginary; and fiction and poetry published for the first time in English. Not simply a critique of imperialism, this volume presents politically engaged commentary that suggests a way forward for a site of global contact and conflict.