Heading out from Spain, the main problem Gaspar encountered was one of timing. He was entering this new career close to the end of the 'Golden Age of Piracy,' which began in the late 1600s and lasted until the late 1700s. In fact, given the years from 1783 to 1821 before his privately funded pension was to kick in, he may be among the last pirates standing. The problem of timing manifests itself primarily in the fact that most of the more lucrative routes had already been taken. Most of the piracy was concentrated along merchant and trade routes on the Eastern Seaboard and Caribbean, where Captain Edward Teach, for example, after a career as a "privateer," established his territory along the British colony of North Carolina. Those choicer locations, where the pickings were easy, had already been spoken for, forcing Gaspar, like some Florida wildcat, to develop a new territory on the west coast, more specifically Charlotte Harbor. So by 1783 Gaspar and crew had hijacked a ship, sailed to Charlotte Harbor and promptly began a semi-lucrative career of pirating. So without putting a lot of distasteful images in your brain, let's simply say during those years he amassed gobs of money, killed lots of men, terrorized island neighborhoods, attacked untold merchant ships, and kidnapped distressed beautiful women - most of whom were kept, by no small coincidence on Captiva Island, many of whom were wealthy and would bring large ransoms, but not before he would have his way with them. But then there is the Spanish princess named Joseffa de Mayorga who Gaspar kidnapped, did a back-flip over and keeps here on her own island, Joseffa's Island, which he then named after her.^2* And while Halloween seems like an appropriate date on which to celebrate Gaspar's (aka Gasparilla's) legendary accomplishments April first would also be appropriate.

2* Anyone adept at Gaspar's language by now would have realized that Joseffa is phonetically Useppa. What you might not know however is that Spain's Queen Santa Isabell was Gaspar's inspiration for naming Sanibel Island.