The pirate fleet had been assembled in haste but not without care, the promise of booty from a Spanish treasure galleon being more than most corsairs in the area could resist. Not a single galleon had been taken in nearly the entire year previously, with all the ships known to attempt the endeavor lost with all hands. There were wild tales of cannonballs bouncing off the sides of treasure galleons, of their own shot and shell tearing through opposing ships with inhuman accuracy and power, but a confederation of five ships was enough to but all such notions—silly superstition in the eyes of their masters—to rest.

The treasure galleon—Nuestra Señora de la Inmaculada Concepción—was quietly shadowed by a pair of skiffs after leaving Veracruz, but to the surprise of its crew, their course took them not to Havana or the open waters of the Atlantic but to the pirate isle of Nativitad, better known to buccaneers as Natty Cove. Arriving in the harbor, Nuestra Señora drove the smaller pirate craft from the harbor before beginning a bombardment of the settlement itself. Its captain informed Natty Cove via note that it was to surrender itself immediately and submit to search and seizure, but as a pirate town there was no mayor or government to treat with. When one of the shadowing skiffs notified the fleet, they proceded at best speed to intercept their prize and save the city.

The five pirate ships—the Surprise, the Gunsway II, the Howdah Keg, the Fancy Rat, and the Duke of New York—engaged the galleon simultaneously, crossing her “T” in what would usually have been a position for a rout.

Twenty minutes later, four of the five ships were ablaze and sinking.

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