Pirates, Trade Routes, and Coastal Conflict in Florida History

At Shank Gym, the authentic history of pirates and their legacy captivate us, inspiring our gym logo. Beyond their notorious acts of murder and plunder, pirates were entrepreneurs who established a democratic society grounded in meritocracy and pioneered the earliest forms of workers' compensation programs.

Types of Pirate Flags

Jolly Roger (Skull & Crossbones) – Linked to pirates like Edward England and Calico Jack Rackham.

• Black Flag – Meant "give up and you might live."

• Red Flag ("Bloody Flag") – Showed no mercy would be given.

• Bartholomew Roberts’ Flag – Had a pirate standing on skulls marked "ABH" and "AMH" (for "A Barbadian’s Head" and "A Martinican’s Head").

• Edward Teach (Blackbeard)’s Flag – Featured a skeleton stabbing a heart with a spear, symbolizing terror and death.

• Christopher Moody’s Red Flag – Showed a winged hourglass, arm with sword, and skull, meaning time was running out for the captured crew (red flag in picture).

For a great intro to pirate history, I highly recommend Stephen Talty's Empire of the Blue Water, which inspired this post.

Early Piracy (1500s - 1600s)

Spanish Treasure Fleets & Privateers

• Once Spain set up its colonies in the New World, treasure fleets were regularly shipping gold, silver, and other goods back to Spain.

• The Florida Straits turned into a risky route where Spanish galleons often got hit by English, French, and Dutch privateers (basically pirates with government approval).

• One of the early privateers was Sir Francis Drake, who attacked St. Augustine in 1586 and burned down the Spanish settlement.

The Golden Age of Piracy (1660s - 1730s)

• Back in the late 1600s and early 1700s, piracy was at its height in the Caribbean, and Florida was a prime hangout.

• A bunch of pirates made use of Florida’s islands, inlets, and secret coves to launch attacks on Spanish ships.

A historical depiction of Blackbeard the pirate, as showcased by the Smithsodean Institute, illustrating his menacing presence with a drawn sword and surrounding ships.

Pirate Dream Team

• Blackbeard (Edward Teach) – Mostly hung out around the Carolinas, but people say he might have cruised through Florida.

• Calico Jack (John Rackham) – Did his pirating thing in the Caribbean, but could have sailed close to Florida.

• Anne Bonny & Mary Read – Famous lady pirates who teamed up with Calico Jack.

• Henry Jennings – Hit up the Spanish treasure from shipwrecks off Florida’s coast back in 1715.

The 1715 Treasure Fleet Disaster

• A Spanish treasure fleet got wiped out by a hurricane near Florida's east coast.

• This caught the attention of pirates like Jennings, who swooped in to plunder the wrecks.

• The spots near Vero Beach and Sebastian Inlet are still called the "Treasure Coast."

Piracy in Florida's Frontier (1750s - Early 1800s)

• Even after the peak of piracy was over, Florida was still a hotspot for outlaws, smugglers, and rogue privateers.

• In the late 1700s, Spain and Britain were fighting over Florida, which led to some opportunistic pirate raids.

• Jean Lafitte, a French pirate and smuggler, was active in the Gulf of Mexico and might have used Florida’s waters.

The End of Piracy (Early - Mid 1800s)

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  • The U.S. got Florida from Spain back in 1821, and the Navy started tackling piracy.

  • In the 1820s, Commodore David Porter was in charge of anti-piracy patrols around the Caribbean and Gulf of Mexico.

  • By the mid-1800s, piracy in Florida was mostly wiped out, but smuggling and wrecking (salvaging shipwrecks, sometimes on the sly) kept happening in Key West.

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References

Rediker, Marcus – Villains of All Nations: Atlantic Pirates in the Golden Age (2004)

Cordingly, David – Under the Black Flag: The Romance and the Reality of Life Among the Pirates (1995)

Konstam, Angus – Piracy: The Complete History (2008)

Gosse, Philip – The History of Piracy (1932)

Talty, Stephen - Empire of the Blue Water, (2007).