How America's Richest City Sold Itself to Survive: Key West, Florida

Key West was once more than a tropical island at the edge of America — it was one of the richest cities in the United States, built on shipwrecks, cigar fortunes, sponge docks, and a harbor that connected the Gulf of Mexico to the wider world. But by the twentieth century, that wealth began to disappear. The city that had once lived from the sea was suddenly fighting to survive. Before highways, tourists, postcards, and sunset celebrations transformed its image, Key West was a working island with a hard past. Its streets were filled with sailors, cigar workers, wreckers, merchants, and families who depended on industries that slowly collapsed one by one. When the money left, the island was forced to make an impossible choice: fade into poverty, or sell its own history, beauty, and identity to stay alive. This is the story of how America’s once-rich island city reinvented itself — not through factories, railroads, or industry, but through memory, myth, tourism, and survival. Key West did not simply become a vacation destination. It turned its past into its future. Copyright & Fair Use Disclaimer • This video is a non-commercial, educational history documentary created for commentary, criticism and research. • Some archival photos and footage are used under the principles of Fair Use (Section 107, U.S. Copyright Act) for purposes such as criticism, comment, news reporting, teaching, scholarship, and research.