I moved to the Florida Keys in 2001, so I could live on an island, sip rum and finish my great Florida novel. It seems like a lifetime ago. When I was researching my first book, “Snorkeling Florida,” every dive captain had their own story about how this reef or that reef was named. 

Curious about the facts and the real stories, I began doing a little research, which became the catalyst that forked the road down which I had been traveling. Except for last year’s “The Florida Keys Skunk Ape Files,” my world has been history, history, history ever since.

It was not until 2010 that I started to get serious about the local history. It was not some fleeting interest and has blossomed into something of a job, if not a career. I have learned a thing or two since taking those first steps. One of those things I have come to recognize is the interconnectedness of the islands. Another is the importance of the conduits that have linked the islands, the communities and the pioneer families.

For the early pioneers, water was the conduit – the Atlantic Ocean, Florida Bay and the Gulf of Mexico provided the only link between the islands and the outpost communities that developed upon them. Later it would be Henry Flagler’s Over-Sea Railroad and then State Road 4A, better known as the Overseas Highway. Because of these conduits, these links that connect one island, one community, and one family to another, it is difficult to tell a Key West, Marathon, Islamorada, Key Largo, or even Elliott Key story without telling a larger Florida Keys story. 

As someone who spends an excessive amount of time researching, reading and learning about these islands, what becomes clear over and over again is that the more I learn, the less I know about the local history. The legendary pirate Black Caesar has become the latest example. 

I knew nothing but the usual stories often told between sips of rum or other adult beverages 10 years ago. Black Caesar was an escaped slave who used Elliott Key as his pirate lair, and that is why Caesars Creek is still called Caesars Creek on modern charts. I have learned that the Black Caesar legend is bigger and more fantastic than I could have ever imagined. In fact, I have been working on a new book called “The Black Caesar Files to make sense of all the stories about his remarkable life.

Like every other great Florida Keys story, a single island cannot contain the legend of Black Caesar. While his story is primarily focused on Elliott Key, it extends as far down the island chain as Key West and as far west as the barrier islands of Southwest Florida. According to the article “Pirates and Treasure Trove of South Florida,” written by David O. True and published in Tequesta Number VI, 1946: “Caesar was an escaped negro slave, half Scotch from his father and a negro mother. Escaped and joined the pirates, and worked himself up. He moved to San Carlos Bay on the west coast when settlers began to settle along the east coast. Was finally whipped and captured and taken to Key West by U.S. Sailors where he was burned to death tied to a tree, fire lit by the widow of the preacher from Baltimore whose eyes he had burned out and who engineered his capture on Sanibel Island.”

No matter what the author wrote, none of it is true. Even though it is entirely legend, the Black Caesar story is fascinating and deserves more attention, and it has also become one of my favorites. At this point, I might know more about the many lives of Black Caesar than just about anyone. 

When I moved to the Florida Keys in 2001, I had never heard of him. Now, I consider myself an expert. Still, I am continually surprised by new historical facts revealed about him. Included in this is the fact that five Black Caesars have been identified so far, and who knows what tomorrow might reveal? 

Thankfully, I moved to the Florida Keys in 2001, so I could live on an island and write. I never thought I would be writing my own column for a newspaper or books about the local history, especially pirates, but then sometimes roads fork, and instead of going left, you go right. Fortunately, nothing goes better with a legendary pirate story than rum.

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Brad Bertelli is an author, speaker, and Florida Keys historian. His latest book, “The Florida Keys Skunk Ape Files,” is a fun blend of two of his favorite subjects — Florida Keys history and the Skunk Ape.