The story of Jose Gaspar lacks certainty, based mainly on tales as wobbly as the planks his prisoners walked.
Many of the stories about Gaspar are fairly consistent and claim he was born sometime in 1756 in Spain. He terrorized the coastal waters of West Florida in the early 19th century. After he turned from a loyal member of the Spanish Navy to an outlaw of the sea, he made his crew call him “Captain Gasparilla.” In the first 12 years, Gasparilla captured or burned 36 ships. The crews of the ships he destroyed chose to either join his crew or walk the plank.
Gasparilla once reportedly captured a Mexican princess and forcefully tried to win her love. When that failed, he beheaded her but later regretted his decision. He buried her on a nearby island that he named after her.
In 1821 when Spain sold the Florida territory back to the United States, Gasparilla retired. As he and his crew were dividing up their treasures they saw a large merchant vessel, an opportunity they couldn’t pass up. However, luck would have it that it was an American pirate-hunting ship. After Gasparilla’s ship was struck by cannon balls and gunfire, he chained an anchor to his waist, filled his hands with as much gold as he could, and leapt from the the boat.
As he jumped, he yelled, “Gasparilla dies by his own hand, not the enemy’s!”