A Short History of Key West

By Tom Hambright, Monroe County Historian

This small coral island’s strategic location has played a major role in its history and a part in the development of the United States and Florida. Key West is on the treacherous Florida Reefs and lies at the western gateway to the Florida Straits, one of the world’s busiest sea lanes. Across the Florida Straits are Cuba and the Bahamas, Key West’s foreign neighbors.

Native people settled on the island up to 1,000 years before the Europeans arrived. Legend maintains bones were left on sand dunes along the south shore of the island and later when the Spanish explorers found the bones, they named the island Cayo Hueso which means Bone Island. Hueso is pronounced “weso;” the English corrupted it into “Key West.”

Juan Pablo Salas, a Spanish military officer of St. Augustine, received the island as a land grant in 1815. When Florida became a territory of the United States in 1821, Salas sold the island to John Simonton, an American businessman, for $2,000. Simonton was aware of the island’s deep and natural harbor and its strategic location. Simonton would soon take in John Whitehead, John Fleming and Pardon Greene as partners.

In 1822, the Navy ordered Lt. Matthew C. Perry to the island to make a survey and to claim it as part of the U.S. Territory of Florida. The next year Commodore David Porter arrived and established the first Naval Station on the island as a base for his Anti-Pirate Squadron. From here he was able to clear the Caribbean of pirates.

In 1823, Monroe County, named for President Monroe, was created. The County originally included all of South Florida. Although Key West was made the county seat, it was not until 1828 that it became incorporated as a city. By 1831, an Army post had been established and in 1845 the construction of two great forts, Fort Jefferson at the Dry Tortugas and Fort Taylor in Key West, had begun. Due to the military presence and a civilian population, which did not favor the Confederate States, Key West was the only southern city to remain in the Union for the Civil War. The Navy’s Gulf Blockading Squadron brought a total of 199 captured ships, attempting to run the Union blockade of the Confederate States, to Key West to be adjudicated in the Federal Court.

The first white American settlers on the island were New Englanders and Bahamians who were wreckers and fishermen. Wreckers saved ships stranded on the Florida Reef and were regulated by the Federal Court in Key West, which awarded the wreckers a percentage of the ships and cargoes saved. Several great fortunes were made from this industry. The construction of lighthouses on the reef began the decline of wrecking but the sea-going men developed other sources of income from the sponging, shipping, and fishing industries.

In the 1870sCubans fleeing the revolution began to settle in Key West. They brought Latin tolerance, gaiety and an entrepreneurial spirit. Key West became known as the cradle of Cuban Independence when Jose Marti came to the island seeking support for his Partido Revolutionary Cubano. The Cubans also brought the hand-rolled Cuban cigar industry to Key West and by 1900 knew the island as “Cigar City USA.” The 1890 Federal Census showed Key West as the largest city in Florida.

In 1898, the USS Maine sailed from Key West to Havana Harbor where it was destroyed by an explosion. Some of the dead were brought here for burial and the wounded were taken to the Marine Hospital and St. Mary’s Convent in Key West. The destruction of the USS Maine led to the Spanish-American War which resulted in a free Cuba with very close ties to Key West. After the war, the Naval Station was expanded to support and protect the new nation of Cuba and to guard the Panama Canal, which was under construction.

In the early 1900s, in need of a deep-water port for his railroad, the desire to connect the state’s largest city to his railroad and seeing the possibility of trade with Cuba and the new Panama Canal, Henry M. Flagler ordered the Florida East Coast Railroad built to Key West. The first train with Flagler onboard arrived in Key West on January 22, 1912.

During World War I, the island was a strategic training base for Army and Naval forces. Prohibition, which began after the war, was an invitation to rum running from the Bahamas and Cuba. Bootlegging became a lucrative business. In the meantime, the big Florida land boom was sweeping mainland Florida and Key West’s desire to take part led to the construction of a highway with a ferry/water gap which was completed in 1927 to run alongside the railroad; the future of the island seemed assured.

Then came the Great Depression. Key West was one of the earliest and hardest hit. Causes were many… collapse of trade with Cuba, decline of the cigar industry, closing of the Naval Station and the Labor Day hurricane of 1935 that destroyed the railroad in the Upper Keys. These events resulted in the creation of a unique experiment in rehabilitation. In 1934 the legal, political and economic problems of the County and its only city, Key West, were turned over by the Governor of Florida to the Emergency Relief Administration. This large-scale plan was aimed at attracting tourists and to make Key West “the Bermuda” of the United States. The completion of the Overseas Highway using the old railroad bridges to eliminate the ferry in July 1938 saw tourists arriving to improve the economy. But full recovery would not happen until World War II saw reactivation of the Naval Station, increases in military and other related personnel, the establishment of the Seaplane Base, the Boca Chica Air Station and the Naval Hospital. The Fleet Sonar School trained more than 18,000 Sonar operators who helped win the Battle of the Atlantic against the German U-boats.

Key West remained a major military base and played an important part in national defense during the Cold War. The Base and Key West’s climate attracted President Harry Truman, who spent eleven working vacations in Key West during his term in office. Key West was again on the front line during the Cuban Missile Crisis of 1962. During the early 1970s military presence was considerably reduced. Once again Key West turned to tourism to fuel the economy. The 1980s and 90s saw a considerable increase in the number of tourists, as the military presence grew smaller.

One of the main reasons for the islands popularity as a vacation destination, aside from the year-round perfect climate, is the fascination with the Old World scale and extraordinary number of 19th century houses in Old Town, in fact, the largest historical district of wooden structures on the Department of the Interior’s National Register of Historic Places. That so many wooden houses from the last century still exist in such close proximity is due to a number of historical reasons. During the 1930s, when most parts of the U.S. were considering Victorian buildings outmoded and replacing them with structures in a modern idiom, Key West was too impoverished to partake in wanton demolition. For obvious reasons, very little rebuilding took place during the war years. By the late 1940s and into the 1950s, housing shortages were able to be satiated with all the acres of vacant land in New Town suitable for economical tract housing development. Also, the hard Dade County pine used to construct the 19th century houses in Old Town had endured the test of time and in these years of the baby boom, it would have been counter productive to remove these perfectly serviceable residences. Houses too large for modern families were carved up into apartments. By the late 1950s, forward thinking individuals were bright enough to recognize the treasure of history and architecture that had survived in Old Town and began to actively work toward protection and preservation. In 1960, the Old Island Restoration Foundation was founded to protect and restore historic buildings of Key West. While other parts of the world regret the loss of their heritage via the forces of modernization, Key West stands proud with its rare piece of American history protected for now and many generations to come.