ong before Johnny Depp made teenage girls swoon by caking on


the eyeliner and acting like a slightly effeminate palsy patient on acid in Disney’s Pirates of the Caribbean franchise, SW Florida had its fair share of unsavory swashbucklers. While perhaps none of our homegrown marauders were nearly as dreamy or charming as Captain Jack Sparrow, they nevertheless plundered and pillaged their way into our hearts and history books in ways that would make Depp envious. After all, pirates are part of a golden age in history; an age when men were


truly men and only the strongest survived. It was a time when hard, rugged sailors explored the seven seas while sporting ruffled shirts and billowy Capri pants, drinking copious amounts of rum, and constantly attempting to usurp one another’s “booty.” On second thought, those may not be the best examples of their legendary machismo. However, pirates of yore were also known to rock eye patches, fire off cannonballs at enemy ships, and engage in massive swordfights (the cool kind that is, not the drunken collegiate pool party kind). So in honor of our one-eyed, peg-legged predecessors, we have compiled


a list of our favorite seafarers from around the state - so strap on your boot-toppers, leave the Revlon at home, and prepare to uncover buried treasure from the illustrious, if not altogether scrupulous, history of the Sunshine State. • Ponce de Leon was not a pirate per se, but the man who discovered


known as Gasparilla, whose name inspires the extravagant annual Pirate Festival in Tampa. According to legend, the opulence of Gasparilla’s treasure was unparalleled, amassed during the late 18th and early 19th centuries by sacking every possible ship up and down the Florida coastline. Allegedly, the bloodthirsty buccaneer kept captured women forced to serve as his concubines, sold into slavery, or traded for ransom on land we now know as Captiva Island. In 1821, Gasparilla’s ship was attacked by a U.S. Navy man-of-war disguised as a helpless merchant vessel. As the pirate’s ship was pummeled by enemy cannons, Gasparilla chained the anchor around his waist and jumped overboard, shouting, “I die by my own hand, not the enemy’s!” – a battle cry since adopted as the official motto of the Tampa Bay Buccaneers. Please come back, Jon Gruden. • Black Caesar was an 18th century African pirate who terrorized ships


and named this state surely deserves to be on our list. The fearless Spanish explorer was seeking the Fountain of Youth in April of 1513, when he washed ashore on the beaches of what is now the city of St. Augustine. He claimed the land for Spain and named it Pascua de Florida (Festival of Flowers). Luckily for us, that name narrowly beat out the apropos name suggested by his crew, Pantano Grande (Big Swamp). Sadly, Ponce de Leon died in 1521 of an arrow wound at the hands of Calusa Indians near present day Fort Myers before finding the fabled Fountain of Youth. Today, tourists flock to St. Augustine’s 15 acre Fountain of Youth Archaeological Park to drink from a natural spring touted to be the actual Fountain of Youth. It’s worth a try! According to our sources, that’s Demi Moore’s secret, but don’t tell Ashton! www.fountainofyouthhlorida.com • Perhaps Florida’s most infamous pirate was Jose Gaspar, better


also known as Blackbeard, operated as a pirate on the east coast of the United States, including the waters of Florida. Coincidentally, Black Caesar was one of Blackbeard’s primary lieutenants aboard his infamous ship, Queen Anne’s Revenge. Allegedly, the crew of Queen Anne’s Revenge was obsessed with black, serving as early acolytes of the Goth movement. However, one can hardly blame Teach for adopting the cognomen of Blackbeard. After all, not very many pirates would willingly surrender to the foppish British Captain Edward Teach. Teach had a thick black beard which gave him a fearsome looking visage, and he reportedly used intimidation rather than violence to elicit cooperation from those he robbed. To this end, Blackbeard flew a flag depicting a skeleton spearing a heart and toasting the devil. Scary stuff for someone whose name sounds like a biology professor from Andover! • Calico Jack Rackham was an English pirate pillaging in the early 18th


• For many years in the early 18th century Englishman, Edward Teach,


century who got his nickname from the calico clothing he often wore. Aside from being voted “Worst Dressed Pirate,” Calico Jack is remembered for designing the Jolly Roger flag with its infamous skull and crossed swords. Now mainstream, the Jolly Roger can be found on screen-printed Urban Outfitter t-shirts in malls across the country. In 1720, Calico Jack was captured in Jamaica while at anchor, promptly tried, then tarred and hanged for piracy. Anne Bonny, Rackham’s shipmate and lover, was asked to testify on his behalf at trial, where she told the court the famous line, “If he had fought like a man, he need not have hanged like a dog.” Historians agree that this was one of the first documented cases where a woman turned traitor because her man refused to wear the clothing that she liked.


Thus concludes coverage of our top five favorite scallywags from SW


Florida lore. There are countless tales about these and other pirates who were busy burying treasure along our coasts – but does “X” really mark the spot? Don’t be afraid to borrow grandpa’s metal detector and find out! This summer, try to uncover one of Gasparilla’s caches of coins or Black Caesar’s buried bling at your local beach.


Finally, below are a few more famous Captains who didn’t quite make


the sabre cut, but deserve a brief honorable mention: • Captain Billy Bowlegs – There is no official documentation proving


such a person even existed, but that doesn’t keep the residents of Fort Walton Beach from drinking to his memory at their annual Pirate Festival. Well played, Bowlegs. • Captain Morgan – Not only is the flamboyantly attired Morgan


responsible for countless successful frat parties, but his raised knee pose has become one of the most easily recognizable cultural icons since Hammer Pants in the early 90s. • Captain Ron – For those of you who haven’t seen Kurt Russell’s


in the Florida Keys for decades. Coincidentally, Black Caesar shares his name with the newest addition to the Bad Boy Records lineup, but that is a different article. This swarthy swashbuckler kept most of his booty and an alleged harem on present day Caesar’s Rock, one of the three islands located to the north of Key Largo, which was eventually named in his honor. In 1718, Black Caesar was captured and hanged for piracy in Williamsburg, Virginia, never realizing his dream of starting an eponymous salad dressing line.


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portrayal of the lovably dim, eye-patch clad Captain Ron, get thee to a Blockbuster immediately. The flick, Captain Ron, is perhaps the most underrated film of all time. • The Captain & Tennille – Neither is an actual captain, but they do


have quite the enthusiastic following in this area. The pop duo steals our hearts every time they rock “Love Will Keep Us Together.” • Captain America – Need I say more? I think we’re done here.


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