You can see her coming from miles away—a ship with masts, lurching ever-nearer, slowly coming out of the wide, gleaming bay and up the Hillsborough River.
Eventually, you’ll spot it: the black flag bearing a white skull over crossbones, a symbol of unmistakable meaning. The crew will debark at a bend in the river that cuts through the city. They’ll find the mayor, demand the key to the city, and delve into revelries.
There’s a bustle on deck. Tankards clack, people shout, though you probably can’t hear them because of the noise a smaller fleet of gathering vessels stirs.
But the sailors on them aren’t here to repulse the invaders; they’ve congregated to welcome them. That’s right—in Tampa, these “pirates” are honored guests.
Welcome to the Gasparilla Festival.
It began in 1904 when Ye Mystic Krewe of Gasparilla, a group of Tampa citizens, held the first “invasion.” Since then, it’s evolved into a tradition that draws crowds and boosts cash flow for local businesses.
It’s named after the pirate Jose Gaspar. Search for info on him, and you’ll find a patchwork of lore. Though his existence is questionable, he’s the festival’s “patron rogue.”
The event is filled with festivities: fun runs, live music, even a flotilla of yachts, pontoons, and fishing boats. The chief spectacle is a parade with pirate ship floats that pass through city streets. Those aboard—many in pirate garb—hurl candy and beads to packed crowds lining the roadways.
“Pirates” sail the Jose Gasparilla II into downtown, and amidst smiles and jest, the mayor hands over the key to the city.
More than 300,000 likely will attend. Seems like harmless fun—until you crack open a history book.
Pirates were a scourge of trade throughout the New World. With fast, heavily armed vessels, they patrolled shipping lanes and hunted down merchant and treasure ships like sharks after blood. They’d also strike coastal settlements, pillaging, raping, and killing inhabitants.
It was a terrifying and brutal reality for those on America’s East Coast and speckled about the islands dotting the Western Hemisphere tropics and the Caribbean. Nations with financial stake and an obligation to protect citizens and colonists in the New World had them hunted out.
While Tampa police will handle a few drunk and disorderly citizens at the festival, the city will hardly resemble one sacked by pirates.
Some still roam, targeting freighters and container ships. But culture, it seems, trivializes piracy (at least that of antiquity) through books, shows, and films, such as Disney’s “Pirates of the Caribbean” franchise, cajoling mere chuckles and eye-rolls. And although the pirates who “invade” Tampa for a spell are armed with mostly beaded necklaces and booze, a nagging question hovers: Is this a legacy we should be celebrating?
The dilemma speaks to a broader issue: In refusing or simply failing to educate ourselves on the past, we’ve fallen to accepting, even glorifying, the wrongs of those before us. Swapping true history for revelry has resulted in a celebration of treachery; Tampa’s swashbuckling masquerade dances around the ugly reality of piracy so many sailors and settlers in the New World witnessed.
A 20-minute drive from Tampa will land you in a town called Brandon. That’s where I grew up. It’s a quiet place, with stretches of neighborhoods strewn through cow pastures and patches of swampy, scrub oak runs.
My grandfather lived nearby. He brought my brother and I to local reenactments, museums, even Seminole burial mounds. If it had to do with history, he loved it, and he engrained that love in us—and through that sort of education, and his own life, taught us that virtue, not notoriety, or dash, or even fame, are to be praised.
That said, it felt fitting to present two figures significant to Tampa who deserve to be remembered. Research them yourself. It’ll be worth it:
- Vicente Martinez-Ybor: A Cuban businessman and namesake of Tampa’s Ybor City district, he developed a section of Tampa many of his fellow immigrants would come to call home. His efforts to employ and house fellow immigrants helped the area thrive.
- Kate Jackson: Though her father and a brother served as Tampa mayors, Jackson devoted herself to a variety of causes, including improving public infrastructure and works, helping establish both the Tampa Civic Association and the city’s first public play-ground, and other philanthropic causes.
The Gasparilla Festival eventually ends, and the pirates debark (literally), and although digging probably won’t turn up treasure chests, it should yield something worth a whole lot more valuable—that is, if you’re searching for history rather than buried gold.
And if what you find scares you, don’t worry; forgetting it—leaving it buried—would mean something far scarier.
Scarier than pirates.