In September 1928 a tremendous storm impacted the Caribbean, with particularly devastating effects in Guadeloupe, Puerto Rico, and Florida. This hurricane exposed the ways in which the disastrous legacies of colonialism and slavery structured the infrastructure and institutions of the region deep into the twentieth century, decades after abolition. The responses of governments and private organizations to the cyclone were shaped and limited by these structures inherited from slavery and both prior and ongoing colonialisms. This dissertation explores not only these responses, but how members of these communities participated in these colonial responses and shaped the memory and legacy of these storm through cultural productions after its passing. Incorporating government reports, newspaper articles, Red Cross records, personal diaries, and interviews along with songs, paintings, literature, and more sources in English, French, and Spanish from national archives, university special collections, local historical societies, commemorative sites, and museums in North America, the Caribbean, and Europe this project is multilingual, multi-archival, and transnational. In Guadeloupe, I show that despite its special status within the empire allowing some local input in the recovery, the French colonial service from exercising significant control over the rebuilding efforts. In Puerto Rico, I argue that, by fostering relationships between professionals and bureaucrats on both sides through collaboration in recovery and loans to farmers which created private debt owed to the U.S. government, the colonial relationship with the U.S. was strengthened. In Florida I demonstrate that Jim Crow structures shaped racialized injustices, including at least one lynching and forced labor, in the wake of the storm. Finally, I analyze art, music, literature, community archives, and sites of commemoration from throughout the region. I show how collectively these formed an infrastructure of public memory, an infrastructure itself shaped by colonialism, which allowed citizens to shape and interpret the historical memory of the storm.