My Latest Work – Pirate Illustrations for the Travel Channel

Last fall, I was asked to do some illustrations for a series on The Travel Channel called “Hidden City,” dealing with infamous crimes in places that people like to visit. One of the episodes – which aired Tuesday, January 24 at 9 PM – is about the Florida Keys, and involves a notorious pirate named Black Caesar, who roamed the Keys in the late seventeenth and early eighteenth centuries. The filmmakers at Crazy Legs Productions here in Atlanta, producers of the series, needed some illustrations of the pirate, since very few pictures had ever been done of him. I accepted the commission, and below are the results. I hope you enjoy them. I also hope you got to watch the show. It was very entertaining. If not, I think you can get a copy from The Travel Channel web site.

Pirate Black Caesar with Treasure

The story of Black Caesar is interesting and, in may ways, chilling. He was an African chief of immense size, who, after many failed attempts, was finally lured onto a slave ship with the promise of shiny trinkets. Once on board, the ship raised anchor and set sail for the New World. But on the way, the ship was caught in a storm and all hands were lost – all except for Black Caesar and a sailor that had befriended him. Together they escaped in a longboat to the Florida Keys.

Pirate Black Caesar with Treasure - Detail

Once there, the two castaways decided to turn to piracy, robbing ships by posing as sailors in distress. These were the days of the Spanish Main, when a tremendous volume of gold mined in America was converted into doubloons and then shipped in galleons back to Spain. The idea was to come alongside a vessel in their longboat, and, once on board, to pull out their blunderbusses. The ploy of the pirates worked so well that, over time, they amassed a fortune, as well as built up a harem of over 100 kidnapped women.

Pirate Black Caesar Killing Partner

Black Caesar was a heartless tyrant, who had little regard for anyone but himself. Often, when he and his partner went off on a raid, they left their prisoners without food and water. When they returned, many would be dead. Often the pirates quarreled. On one occasion, they got into such a heated debate over one particularly choice female captive, that Caesar finally ended the argument, and his partnership, on the blade of his knife.

Pirate Black Caesar Killing Partner - Detail 1

As I worked on these paintings, I was struck by the fact that such gruesome events had taken place in such an idyllic setting. I also wondered what in the world these pirates thought they were going to do with so much gold. It’s not as if they could go somewhere to spend it. It seems the surroundings, and the gold, were wasted on these men.

Pirate Black Caesar Killing Partner - Detail 2

Something else I wondered about: What were these women doing in the New World? Were they here with the Conquistadors? Or were they pilgrims, come to the New World to make a new life? If so, what a shocking turn of events – to end up in Black Caesar’s harem, or worse!

Pirate Black Caesar Being Burned to Death

Eventually, Black Caesar was captured and burned at the stake. The wife of one of his victims, a preacher whose eyes Caesar had burned out, had the honor of lighting the pyre. I suppose most of Caesar’s women eventually returned to civilization. But he did have some children by them; and their descendants are said to roam the Florida Keys to this day.

Pirate Black Caesar Being Burned to Death - Detail 1

There’s an alternate ending to this story: instead of being captured and burned, it is said that Black Caesar later joined Blackbeard in the Carolinas, where he became Blackbeard’s right-hand man. Eventually, both men were captured and hung. Whether this was another pirate calling himself Black Caesar, or the same as the one that plagued the Florida Keys, is unknown.

Pirate Black Caesar Being Burned to Death - Detail 2

Also unknown is the whereabouts of Black Caesar’s treasure. Floridians are convinced it is still hidden somewhere among the Keys; and many a treasure hunter has ventured forth hoping to find it, only to return empty-handed. No telling how many human skeletons would be mixed among the chests of doubloons, if they were to find it, since dead men tell no tales.

I have paintings and prints for sale, and I also do commissions. If you’d like to see more of my work, go to or email me at

Waitsel Smith

Waitsel Smith, January 17, 2012

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Text © 2012 Waitsel Smith. Artwork © 2012 Crazy Legs Productions. All Rights Reserved.

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{ 3 comments… add one }
  • Dennis Overton March 3, 2012, 4:29 PM

    Awesome work!

  • Shelton February 14, 2014, 10:30 PM

    Cool story, nice work!

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