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 Cayo Hueso

Cayo Hueso is the original Spanish name for the island of Key West. Spanish-speaking people today also use the term Cayo Hueso when referring to Key West. It literally means "bone key". It is said that the island was littered with the remains (bones) from an Native American battlefield or burial ground. The most widely accepted theory of how the name changed to Key West is that the word "hueso" (pronounced weso) sounds as if it could mean "west" in English. Other theories of how the island was named are that the name indicated that it was the westernmost Key, or that the island was the westernmost Key with a reliable supply of water.

In 1761, when the Kingdom of Great Britain took control of Florida, the community of Spaniards and Native Americans were moved to Havana. Florida returned to Spanish control 20 years later, but there was no official resettlement of the island. Informally the island was used by fishermen from Cuba and from the British Bahamas, who were later joined by others from the United States after the latter nation's independence. While claimed by Spain, no nation exercised de facto control over the community there for some time.

Matthew C. Pettyfield and the Opening of "Thompson's Islya"

In 1815 the Spanish governor in Havana, Cuba, deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in St. Augustine, Florida. After Florida was transferred to the United States, Salas was so eager to sell the island that he sold it twice - first for a sloop valued at $575, and then to U.S. businessman John W. Simonton, during a meeting in a Havana café, for the equivalent of $2,000 in pesos in 1821. The sloop trader quickly sold the island to a General John Geddes, a former governor of South Carolina, who tried in vain to secure his rights to the property before Simonton, with the aid of some influential friends in Washington, was able to gain clear title to the island. Simonton had wide-ranging business interests in Mobile, Alabama. He bought the island because a friend, John Whitehead, had drawn his attention to the opportunities presented by the island's strategic location. John Whitehead had been stranded in Key West after a shipwreck in 1819 and he had been impressed by the potential offered by the deep harbor of the island. The island was indeed considered the "Gibraltar of the West" because of its strategic location on the 90-mile (140 km)–wide deep shipping lane, the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico. On March 25 1822, Matthew C. Perry sailed the schooner USS Shark (1821) to Key West and planted the U.S flag, physically claiming the Keys as United States property. Perry reported on piracy problems in the Caribbean. Perry renamed Cayo Hueso (Key West) to "Thompson's Island" for the Secretary of the Navy, Smith Thompson, and the harbor "Port Rodgers" for War of 1812 hero John Rodgers. Neither name was to stick. In 1823 Commodore David Porter of the United States Navy West Indies Anti-Pirate Squadron took charge of Key West, which he ruled (but, according to some, exceeding his authority) as military dictator under martial law.

First Developers

Soon after his purchase, Simonton subdivided the island into plots and sold three undivided quarters of each plot to:

  • John Mountain and U.S. Consul John Warner, who quickly resold their quarter to Pardon C. Greene, who took up residence on the island
  • John Whitehead, his friend who had advised him to buy Key West
  • John Flemming (nowadays spelled Fleming)

John Simonton spent the winter in Key West and the summer in Washington, where he lobbied hard for the development of the island and to establish a naval base on the island, both to take advantage of the island's strategic location and to bring law and order to the town. He died in 1854.

Pardon C. Greene is the only one of the four "founding fathers" to establish himself permanently on the island, where he became quite prominent as head of P.C. Greene and Company. He also served briefly as mayor. He died in 1838 at the age of 57.

John Whitehead lived in Key West for only eight years. He became a partner in the firm of P.C. Greene and Company from 1824 to 1827. A lifelong bachelor, he left the island for good in 1832. He came back only once, during the Civil War in 1861, and died the next year.

John W.C. Flemming was English-born and was active in mercantile business in Mobile, Alabama, where he befriended John Simonton. Flemming spent only a few months in Key West in 1822 and left for Massachusetts, where he married. He returned to Key West in 1832 with the intention of developing salt manufacturing on the island but died the same year at the young age of 51.

The names of the four "founding fathers" of modern Key West were given to main arteries of the island when it was first platted in 1829 by William Adee Whitehead, John Whitehead's younger brother. That first plat and the names used remained mostly intact and are still in use today. Duval Street, the island's main street, is named after Florida's first territorial governor, who served between 1822 and 1834 as the longest serving governor in Florida's U.S. history.

William Whitehead became chief editorial writer for the Enquirer, a local newspaper, in 1834. He had the genius of preserving copies of his newspaper as well as copies from the Key West Gazette, its predecessor. He later sent those copies to the Monroe County clerk for preservation, which gives us a precious view of life in Key West in the early days (1820-1840).

U.S. Civil War

During the American Civil War, while Florida seceded and joined the Confederate States of America, Key West remained in U.S. Union hands because of the naval base. However, most locals were sympathetic to the South, and many flew Confederate flags over their homes. Fort Zachary Taylor, constructed from 1845 to 1866, was an important Key West outpost during the Civil War. Construction began in 1861 on two other forts, East and West Martello Towers, which served as side armories and batteries for the larger fort. When completed, they were connected to Fort Taylor by railroad tracks for movement of munitions. Fort Jefferson, located about 68 miles (109 km) from Key West on Garden Key in the Dry Tortugas, served after the Civil War as the prison for Dr. Samuel A. Mudd, convicted of conspiracy for setting the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln.

The Emancipation Proclamation went into immediate effect in Key West on January 1, 1863, and local blacks celebrated accordingly.

In the late 19th century, salt and salvage declined as industries, but Key West gained a thriving cigar-making industry.

By 1889 Key West was the largest and wealthiest city in Florida.

Many Cubans moved to Key West during Cuba's unsuccessful war for independence in the 1860s and 1870s.

Overseas by Rail and Road

Key West was relatively isolated until 1912, when it was connected to the Florida mainland via the Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway (FEC). Flagler created a landfill at Trumbo Point for his railyards. The Labor Day Hurricane of 1935 destroyed much of the railroad and killed hundreds of residents, including around 400 World War I veterans who were living in camps and working on federal road and mosquito control projects in the Middle Keys. The FEC could not afford to restore the railroad.

The U.S. government then rebuilt the rail route as an automobile highway, completed in 1938, which became an extension of United States Highway 1. The portion of U.S. 1 through the Keys is called the Overseas Highway. Franklin Roosevelt toured the road in 1939.

Winter White House

Several U.S. presidents have visited Key West. Harry Truman visited for 175 days on 11 visits during his presidency and visited several times after he left office (see Truman Annex)

Key West was in a down cycle when Franklin D. Roosevelt visited in 1939. The buildup of military bases on the island occurred shortly thereafter.

In addition to Truman, Dwight D. Eisenhower stayed in Key West following a heart attack. In November 1962, John F. Kennedy visited Key West a month after the resolution of the Cuban Missile Crisis. Jimmy Carter held a family reunion in Key West after leaving office.

Ernest Hemingway

Legend has it that Ernest Hemingway wrote A Farewell to Arms while living above the showroom of a Key West Ford dealership at 314 Simonton Street while awaiting delivery of a Ford Model A roadster purchased by the uncle of his wife Pauline in 1928.

Hardware store owner Charles Thompson introduced him to deep-sea fishing. Among the group who went fishing was Joe Russell (also known as Sloppy Joe). Russell was reportedly the model for Freddy in To Have and Have Not. Portions of the original manuscript were found at Sloppy Joe's Bar after his death. The group had nicknames for each other, and Hemingway wound up with "Papa".

Pauline's rich uncle Gus Pfeiffer bought the 907 Whitehead Street house  in 1931 as a wedding present. Legend says the Hemingways installed a swimming pool for $20,000 in the late 1930s (equivalent in 2006 to $250,000). It was such a high price that Hemingway is said to have put a penny in the concrete, saying, "Here, take the last penny I've got!" The penny is still there.

During his stay he wrote or worked on Death in the Afternoon, For Whom the Bell Tolls, The Snows of Kilimanjaro, and The Short Happy Life of Francis Macomber. He used Depression-era Key West as the locale for To Have and Have Not — his only novel set in the United States.

Pauline and Hemingway divorced in 1939, and Hemingway only occasionally visited while returning from Havana until his suicide in 1961.

The six- or seven-toed polydactyl cats descended from Hemingway's original pet 'Snowball' still live on the grounds and are cared for at the Hemingway House, despite complaints by the U.S. Department of Agriculture that they are not kept free from visitor contact, and the Key West City Commission exempted the house from a law prohibiting more than four domestic animals per household.

Tennessee Williams

Tennessee Williams first became a regular visitor to Key West in 1941 and is said to have written the first draft of A Streetcar Named Desire while staying in 1947 at the La Concha Hotel. He bought a permanent house in 1949 and listed Key West as his primary residence until his death in 1983. In contrast to Hemingway's grand house in Old Town, the Williams home at 1431 Duncan Street  in the "unfashionable" New Town neighborhood is a very modest bungalow. The house is privately owned and not open to the public. The Academy Award–winning film version of his play The Rose Tattoo was shot on the island in 1956. The Tennessee Williams Theatre is located on the campus of Florida Keys Community College on Stock Island. 

Williams had a series of rented homes all over the U.S., but the only home he owned was in Key West.

Even though Hemingway and Williams were in Key West at the same time, they reportedly met only once -- at Hemingway's Cuba home Finca Vigía.

Cuban Presence

Key West is much closer to Havana than it is to Miami.

In 1890 Key West had a population of nearly 18,800 and was the biggest and richest city in Florida. Half the residents were said to be of Cuban origin, and Key West regularly had Cuban mayors, including Carlos Manuel de Céspedes, father of the Cuban Republic, who was elected mayor in 1876.  Cubans were actively involved in reportedly 200 factories in town, producing 100 million cigars annually. José Martí made several visits to seek recruits for Cuban independence starting in 1891 and founded the Cuban Revolutionary Party during his visits to Key West. 

The Battleship USS Maine (ACR-1) sailed from Key West on its fateful visit to Havana, where it exploded, igniting the Spanish-American War. Crewmen from the ship are buried in Key West, and the Navy investigation into the blast occurred at the Key West Customs House.

Pan American Airlines was founded in Key West, originally to fly visitors to Havana, in 1926.

John F. Kennedy was to use "90 miles from Cuba" extensively in his speeches against Fidel Castro. Kennedy himself visited Key West a month after the resolution of the Cuban Missile Crisis.

Prior to the Cuban revolution of 1959, there were regular ferry and airplane services between Key West and Havana.

Key West was flooded with refugees during the Mariel Boatlift. Refugees continue to come ashore and, on at least one occasion, most notably in April 2003, flew hijacked Cuban Airlines planes into the city's airport.

Naval Air Station Key West

Key West was always an important military post, since it sits at the northern edge of the deepwater channel connecting the Atlantic and the Gulf of Mexico (the southern edge 90 miles (140 km) away is Cuba) via the Florida Straits. Because of this, Key West since the 1820s had been dubbed the "Gibraltar of the West." Fort Taylor was initially built on the island. The Navy added a small base from which the USS Maine (ACR-1) sailed to its demise in Havana at the beginning of the Spanish-American War.

At the beginning of World War II the Navy increased its presence from 50 acres (200,000 m2) to 3,000 acres (12 km²), including all of Boca Chica Key's 1,700 acres (7 km2) and the construction of Fleming Key from landfill. The Navy built the first water pipeline extending the length of the keys, bringing fresh water from the mainland to supply its bases. At its peak 15,000 military personnel and 3,400 civilians were at the base. Included in the base are:

  • NAS Key West - This is the main facility on Boca Chica, where the Navy trains its pilots. Staff are housed at Sigsbee Park. In 2006 there were 1,650 active-duty personnel; 2,507 family members; 35 Reserve members; and 1,312 civilians listed at the base. In the 1990s the Navy worked out an agreement with the National Park Service to stop sonic booms near Fort Jefferson in the Dry Tortugas. Many of the training missions are directed at the Marquesas "Patricia" Target 29 nautical miles (54 km) due west of the base. The target is a grounded ship hulk 306 feet (93 m) in length that is visible only at low tide. Bombs are not actually dropped on the target.
  • Truman Annex - The area next to Fort Taylor became a submarine pen and was used for the Fleet Sonar School. President Harry S. Truman was to make the commandant's house his winter White House. The Fort Taylor Annex was later renamed the Truman Annex. This portion has largely been decommissioned and turned over to private developers and the city of Key West. However, there are still a few government offices there, including the new NOAA Hurricane Forecasting Center. The Navy still owns its piers.
  • Trumbo Annex - The docking area on what had been the railroad yard for Flagler's Overseas Railroad is now used by the Coast Guard.

Port of Key West

The first cruise ship was the Sunward in 1969, which docked at the Navy's pier in the Truman Annex or the privately owned Pier B. The Navy's pier is called the Navy Mole.

In 1984 the city opened a pier right on Mallory Square. The decision was met with considerable opposition from people who felt it would disrupt the tradition of watching the sunset at Mallory Square.

Cruise ships now dock at all three piers.