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Key West 200: Celebrating the History of Key West

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Happy Birthday!

Guess who's turning 200?!

Key West!

March 25, 1822: Lt. Commander Matthew Perry planted the USA flag on Key West claiming the Florida Keys as United States property.

Of course, there was a little controversy over the actual ownership of Key Wes. The island was sold twice. Two different buyers thought they had purchased it. It was a reverse two for one special.

Here’s the gist of it: In 1815, the Spanish governor of Cuba had deeded the island to a Spanish officer stationed in St. Augustine (Juan Salas). Salas cut two deals, but by 1821 Florida had been transferred to the USA from Spain. A bit of a scam, but it worked.

There was a bunch of back/forth between a former governor of South Carolina who got swindled in the transaction, and John Simonton who paid about $2,000 to Salas.

In fact, the $2,000 deal with Simonton was cut at a café in Cuba in January of 1822.

Simonton got the island based on his deeper connections with the powers in DC.

As a tip of the hat to the game Salas and Simonton played, the 2-for-1 special became an island happy hour tradition. Yep, it goes that far back.

After claiming all of the keys as US property, Perry renamed the island known as “Cayo Hueso:” (Key West) to “Thompson’s Island” after then Secretary of the Navy, Smith Thompson. Of course, a “pay-back” honor given that DC powers sided with him in the ownership controversy.

It was considered the “Gibraltar of the West”. At that time, not all that much was happening in Florida nor in the keys. Mostly some Bahamian and Cuban fisherman would wander over for a stretch to collect wood or do some fishing. Plus, it was (and is) a haven for pirates and salvagers.

After Simonton took control, and with the help of few influential business partners, the island started to build up. A few notes of interest:

  • By the 1830’s, Key West was the richest city, per capita, in the United States.
  • 1846: Heavy damage from the Havana Hurricane
  • 1852: St. Mary’s Star of the Sea built
  • 1845-1866: Fort Zac Taylor built. While Florida succeeded, Key West remained a Union garrison.
  • 1830-1861: Major center of salt production
  • 1860’s on through today: Major producer of cigars (less so today, but you can still get fresh rolled cigars at a few popular spots)
  • 1890’s: Largest city in Florida. By contrast KW was 18,000, Miami 500.
  • 1909, 1910, 1919: Florida Keys and Cuban Hurricanes caused wide spread devastation
  • 1912: Connected to mainland Florida by the Overseas Railway
  • 1927: Pan American airline founded in Key West
  • 1933 Sloppy Joe’s opens
  • 1946: President Harry Truman established a working vacation home, The Little White House
  • 1959: Cuban revolution ceased the regular flights and ferry services between Havana and KW
  • 1982: On April 23rd the Conch Republic was formed and independence from USA briefly established

And of course, most importantly, in 2019 Madda Fella established its base operations at Zero Duval Street, just steps away from Sunset Pier.


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