Pirate legend has always held a certain romanticism, a sense of adventure and freedom that we feel drawn to. In fact, the famous pirates we still read about today—Blackbeard, Calico Jack, Charles Vane—were themselves inspired by stories and legends they’d heard about the pirates who came before them.
One pirate in particular, and his arrival in Nassau, inspired a generation of swashbucklers and began an era we now call the Golden Age of Piracy. That pirate’s name was Henry Avery and his story begins in the last few years of the 1600s.
Among history’s first mentions of Avery are of his position as first mate aboard the privateering ship Charles II, where he led a mutiny and was elected captain. After renaming the Charles II the Fancy, he and his crew began their life of piracy, setting sail for the Indian Ocean.
Along their way, they robbed three English merchant ships, with several crew members from these ships joining Avery’s band of pirates. They also made sure to clean, repair, and strip out unnecessary parts of the Fancy’s structure, making it one of the fastest ships at sea. Now, Avery was ready to take on the ships that would earn him his fortune.
Avery and the other ships in his growing fleet (of which he was now Admiral) prepared to take on the Grand Mughal’s fleet on its way to its annual pilgrimage to Mecca. The 25 ships in the fleet were led by its 80-cannon flagship Gunsway. After chasing the convoy for several days, Avery and his men captured an escort ship. But the real prize was the Gunsway.
The history of piracy would be very different—and, perhaps, much shorter—if the Fancy’s first broadside against the much larger and more powerful Gunsway had been even a few inches off course. But history records that the opening broadside crippled the Gunsway’s mainmast, which left it unable to escape the pirates.
Though Avery and his pirate fleet were outnumbered by the more than 400 aboard the Gunsway, they prevailed after three hours of hand-to-hand fighting on the blood-soaked deck. While many future pirates would gain reputations as men of honor, Avery and his crew were of a different sort. History records a series of horrors committed against the Gunsway’s crew and passengers.
Now it was time to divide the treasure. The Fancy sailed for Bourbon, a French island off the east coast of Madagascar. Here, the crew were given their shares of the spoils, which amounted to about $100,000 in today’s currency—more than many would have been able to spend in a lifetime.
Of course, a score this big made them all criminals and, therefore, on the run. Some stayed in Bourbon, others set off on their own adventures, but Avery and the Fancy set course for Nassau, The Bahamas, halfway around the world.