How much truth is there in the Pirates of the Caribbean auction scene, and what role does Key West play in its history?
Pirates of the Caribbean … what fun! How can you not love the pirate skeleton steering a ghost ship, the prisoners trying to lure the dog closer, and that classic song?
Oh, and the pirate auction. That’s my favorite. Why? Because it reminds me of Key West.
The Pirates of the Caribbean Auction and Key West

A cannon at Fort Jefferson on Dry Tortugas, 70 miles off Key West. Photo by Timothy Moore
Confused? I get it. After all, how could a pirate auction possibly have anything to do with Duval Street, or Fantasy Fest, or sunsets in Mallory Square?
Let’s face it: If there’s anything less Disney than the Duval Crawl, I’ve yet to find it.
Nevertheless, of all the many “little-known facts” I’ve read about Pirates of the Caribbean, I’ve yet to see anyone mention the obvious tie to Key West.
While popular films and art—like the Thomas Kinkade painting—don’t pay much mind to Florida (it’s not often you find a two-story Mediterranean right at a deepwater port), the Pirates of the Caribbean pirate auction could easily have happened in Key West—200 years ago.
Pirate History in Florida

Fort Jefferson on Dry Tortugas, 70 miles off Key West. Photo by Timothy Moore
Here’s a crash course in Florida history: We were perfectly happy as a Spanish territory—twice.
Spain discovered Florida and claimed it in the early 16th century, and except for 20 British years (1763-1783), Spanish wine flowed over Florida shores like… well, Spanish wine.
That is, until 1821, when the US persuaded—through highly suspect covert operations—Spain to hand over Florida.
The very next year, the US government decided Key West was an excellent home base to rid the West Indies of pirates.
Pirate Isn’t a Bad Word!

Photo by Cliff Wang
Everyone knows the Captain Morgan of rum bottle and history fame, right? Well, he was only a pirate if you supported the Spanish Crown. In the United Kingdom, he was Sir Henry Morgan, doing the Crown’s work down in the Caribbean.
To some, he was a hero, a buccaneer; to others, a villain, a dastardly pirate. Other words for pirates? Privateers or wreckers, and, in Key West, “wrecking” was honorable, profitable work.
Say you’re a boat captain hauling gold and silk and rum through the Caribbean and you hit a reef. Bad news, right? That’s where wreckers come in—they “rescue” your ship.
Wreckers got the boat’s crew to safety and, if they could, they’d tow your ship or get it off the reef. If your ship was sinking, they’d salvage what they could before it did.
But were they pirates? Welllll … some historical accounts suggest those wreckers may have lured boats onto reefs so they’d need saving. Also, wreckers negotiated payment for their services as boats were sinking, which doesn’t give a panicking boat captain a lot of time to bargain …
The Key West Pirate Auction

Fort Zachary Taylor in Key West. Photo by Timothy Moore
…which is why the US government based its anti-pirate operations in Key West. We set up a maritime court in Key West, but fighting piracy wasn’t about stopping the pirates (aka wreckers)—the court only had to make sure pirates didn’t take the salvaged booty outside the US.
The court supervised the sale of the booty, not to make sure the captain of the boat (or the country he might have represented) got the money; it made sure the US government got its cut of the proceeds.
How did these sales look? A lot like the pirate auction in Pirates of the Caribbean. People from across the United States would send agents to bid on lace, liquor, and silver from the pirated vessels.
This type of piracy, incidentally, could total $1.5 million—in 1820s money. That’s more than $38 million in today’s dollars. (Isn’t it nice to know there’s still something more expensive than a Disney World vacation?)
These auctions took place in Key West, in public, often on the street or in a public warehouse near the water. And yes, they looked a lot like the auction in Pirates of the Caribbean. Imagineers certainly did their homework.

Photo by Mike Billick
The only bit that may not be true? People selling ladies at auction, which has been removed from the Orlando version of the ride (though it still lingers in the Tokyo version).
Then again, there’s no proof that such sales didn’t happen, either.
So the next time you ride Pirates of the Caribbean, remember, you’re not simply sailing through the imagination of talented Walt Disney World Imagineers—you could very well be looking at history made in Key West.
More Pirates History
Do you love diving deep into Disney history? Are you a mega-fan of Pirates of the Caribbean?
Then make sure you order our Pirates of the Caribbean attraction special, a 32-page exploration of the history, music, Imagineering, and behind-the scenes details of Pirates of the Caribbean in the US and abroad.
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