The biggest clues to a region’s past are in its names: Collier County, Hendry Street, Manuels Branch, Wiggins Pass—stalwart pioneers of Fort Myers and Naples. But behind other names lies a darker legacy.
Like Captiva. The infamous Jose Gaspar reportedly held women captive on this barrier island until their ransoms were paid. Gaspar, who was swashbuckling in the late 1700s and early 1800s, is our best-known pirate, and the force behind many of Southwest Florida’s more scurrilous episodes. Short of stature and outsize in temper, Gaspar is better known as “Gasparilla,” as in Gasparilla Island off the Lee County coast where the pirate headquartered his operation. Legend has it that he kidnapped a beautiful Spanish princess, Useppa (or Joseffa by many accounts), took her to an island even more isolated than Captiva and made repeated advances at her. The woman held firm in her refusal until the incensed pirate sliced off her head.
Naturally, her namesake island is said to be haunted by a headless ghost.
At age 65, Gasparilla decided to pull off one last heist, retire and distribute his wealth among his crew. He identified a British ship to make his final victim. But the ship wasn’t British at all—it was the USS Enterprise, a Navy warship, determined to snare the old pirate. Facing the imminent destruction of his Floridablanca, the pirate captain wrapped anchor chains around his waist and jumped into Boca Grande Pass, reportedly shouting, “Gasparilla dies by his own hand, not the enemy’s!”
His treasure was never fully recovered, though in 2015 a brother and sister who were cleaning out their grandfather’s attic in Tampa found a box containing a skeletal hand, a tattered map of the Hillsborough River, old coins and a photo of a couple who may have been their great-grandparents. As children, their grandfather had told them stories about how his father had recovered part of Gasparilla’s treasure. While we can’t attest to the veracity of the old legends, the family discovery is absolutely true. We read it in the news!
[Incidentally, Gasparilla Island was later found to contain loot of a very different sort—phosphate. By the early 1900s, Boca Grande, the island’s hub, had become the nation’s fourth-busiest port and supplied half the nation’s phosphate. Also famous to Gaspar’s former stomping ground is the 106-year-old Gasparilla Inn & Club, which boasts drawing celebrities including Thomas Edison, Harvey Firestone, Katharine Hepburn and the George H.W. Bush family.]
Read more tales of local lore in our December issue.