The Key West Mystique

Key West Island News

 

Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

DNA with dollar signs(1)

Living in Key West | An island rooted in unabashed exploitation

Living in Key West | An island rooted in unabashed exploitation

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.
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02/23/2026

Key West is an island of unabashed exploitation. Making money is our DNA. Creativity is our currency.

For a 4-square-mile Miami Oolite rock 150 miles from the mainland, Key West sure carries outsized swagger. From the time Solaris Hill poked above the Atlantic Ocean 125,000 years ago, the island’s hypnotic song has lured the adventurous, the avaricious, the outcasts and misfits and the just plain curious. Some stayed; lots died; others simply moved on.

The Calusa and (occasionally) the Tequesta indigenous tribes made Key West a fishing destination, attracted by fresh water and abundant sea creatures. They rarely stayed long and left little behind. In 1513 Spanish explorer Juan Ponce de León mapped the Keys, calling our island Cayo Hueso. The Calusa were not amused by the unwelcome Spaniards and they violently resisted forced conversion to Catholicism. That meant the Spaniards were also not amused, and by the 1760s, they’d wiped out the Calusa with plagues of smallpox, measles, mumps and flu.

In 1822 Key West caught the attention of New-Jersey-by-way-of-Alabama businessman John W. Simonton, who bought the island from Juan Pablo Salas and set up a booming real estate development. The first wave of the American Industrial Revolution paved the way for steamship service to the once-isolated island, which caught the attention of the U.S. military, which turned the island into a major player in the Civil War and the military decided to stick around.

With the second wave of the industrial revolution came highways, Flagler’s legendary Over-Sea Railroad and an influx of the curious and avaricious. Boom times! Making money, building willy-nilly with nary a zoning code. In 1934 the Great Depression pushed Key West into bankruptcy, and Mother Nature wiped out the railroad in 1935. Not to be undone, we invited the artists and writers and tourists down to remake the rock, not because we were lovers of the arts, but because we loved making money.

We’re an intractably creative lot, so if it took exporting turtle soup, harvesting sponges, making cigars, carting tourists around on trolleys, celebrating sunsets, idealizing misogynistic authors, mucking up the ocean and gulf with cruise ships or killing the reef with sunscreen and snorkeling gear, we did what it took to keep the economy rolling.

Tropical Garden

Making money is in our DNA

If you chafe against the idea of DNA with dollar signs, Key West can make you miserable. As I often do, you’ll rail against vacation rentals, traffic, environmental disasters in the making, government corruption and assorted ills of modern society. If you lament the passing of the “good old days,” which are more marketing myth than real life, and think kicking out a couple million visitors and hangers-on will give us OUR island back, well, good luck with that.

None of which means we should capitulate to our worst instincts. Making money isn’t inherently evil and our creativity is a boon when it comes to figuring out how to do the right things even when two forces collide. (I’m in awe of this example: “They” tell you can’t paint your white picket fence with seven rainbow stripes? Hang a mini-fence on the big fence, your bike, the house, the window.)

Our island’s deep-baked moneymaking culture has always been shaped by our creativity and tempered — eventually — by its people, the ones born here and the ones who choose to make it home.

There’s no such thing as the “real Key West.” Key West is a state of mind unique to each of the adventurous, the avaricious, the artists and entrepreneurs, the Bahamian, Cuban and Haitian immigrants, the hippies-turned-retirees, the liberals, conservatives and libertarians and, yes, the tourists, snowbirds and part-time residents. It’s a miracle such a gaggle of humanity lives (mostly) harmoniously so close together.

We have these things in common: We will protect the fragile environment, either because it’s the right thing to do or because we know if we destroy it, there’s no money to be made. We will help those who help others, either because it’s the right thing to do or because we know individuals and nonprofits pick up the load public institutions won’t or can’t. We will take care of those at risk, either because it’s the right thing to do or because we need a workforce that shows up.

Our creativity determines how successfully we balance those either-or imperatives. I’m inclined to think we’ll be OK.

LEARN MORE

https://www.gilderlehrman.org/history-resources/essays/rise-industrial-america-1877-1900

https://www.keyshistory.org/keywest.html

https://www.floridastateparks.org/learn/calusa-native-americans

https://www.hmdb.org/m.asp?m=223755

https://www.facebook.com/watch/?v=273383237410102

6 Comments

  1. Robert Ward

    Your gift of being able to write so exquisitely is appreciated. Thank you

    • Linda Grist Cunningham

      Thank you, Robert!

    • Linda Grist Cunningham

      Thanks, Mike!

  2. Name *

    Well written, and hopefully spot-on.

    • Linda Grist Cunningham

      Thank you — and I hope so, too!

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