The Golden Age of Piracy

According to the legend, Don José Gaspar was a Spanish naval officer who turned to piracy after a falling-out at the court of King Charles III. From a base on the SW Florida Gulf coast, he and his crew preyed on merchant shipping in the Gulf of Mexico for nearly forty years, amassing a vast hoard buried somewhere along Charlotte Harbor.

A 1774 chart of Charlotte Harbor, the labyrinth of mangrove keys and shallow passes Gaspar is said to have used as his base. The names "Gasparilla Island," "Captiva," and "Sanibel" are all woven into versions of the story — though no contemporary record places Gaspar there.

In December 1821 — so the story goes — a US Navy schooner disguised as a British merchantman lured Gaspar's flagship into close range and opened fire. As his ship sank, Gaspar wrapped a length of anchor chain around his waist and leapt into the sea shouting "Gasparilla dies by his own hand, not the enemy's."

No record of José Gaspar exists in any archive — Spanish, British, or American — before about 1900. The earliest written version is this promotional pamphlet, produced by the passenger agent of the Charlotte Harbor & Northern Railway to attract tourists and land buyers to the SW Florida coast. The hand-script "biography" was the railroad's marketing copy.

John Gomez (c. 1778–1900), a real Portuguese hermit who lived alone on Panther Key into his 100s, claimed to be Gaspar's surviving cabin boy. He sold his story for drinks. After his death (drowned tangled in his own fishing net), the legend ballooned. He is the closest thing to a primary source — and almost certainly a fabulist.

Tampa's annual invasion parade has run almost continuously since 1904. The fully-rigged José Gasparilla II — built in 1954, the world's only fully-functional pirate ship of its kind — sails into Hillsborough Bay each January, fires its cannons, and "captures" the city. Hundreds of thousands attend.

A Gasparilla parade float, 1934. By the 1930s the festival had become Tampa's defining civic event. Ye Mystic Krewe of Gasparilla — the original krewe — now shares the streets with dozens of other costumed krewes during the season's parades and "invasions."

The Tampa Bay Buccaneers (NFL, founded 1976), Gasparilla Island, the city of Boca Grande's "Gasparilla Inn," countless local businesses, schools, streets, and parks — all carry the name. A pirate the railway invented to sell lots is now the most recognizable symbol of Florida's Gulf coast.

A 1724 depiction of Blackbeard from "A General History of the Pyrates." He commanded the Queen Anne's Revenge and was feared across the Caribbean and American colonies.

A 1736 engraving commonly identified as Blackbeard (Edward Teach/Thatch). He famously braided slow-burning fuses into his beard to appear wreathed in smoke and fire during battle.

Jean Leon Gerome Ferris' dramatic 1920 painting of the final battle between Blackbeard and Lt. Robert Maynard at Ocracoke Inlet, North Carolina.

A 1724 portrait of Anne Bonny, one of the most famous female pirates. She sailed with Calico Jack Rackham and reportedly fought fiercely when their crew was captured.

A 1724 woodcut of John "Calico Jack" Rackham, who designed the most recognizable Jolly Roger skull-and-crossswords flag. Hanged in Jamaica in 1720.

A museum model of Blackbeard's flagship — originally the French slave ship La Concorde, captured in 1717 and converted to a 40-gun warship. Its wreck was discovered off North Carolina in 1996.