The 19th-century author Howard Pyle is responsible for a great many beliefs about 17th-century pirates, from their flamboyant costumes to their buried treasures. Published after his death, the 1921 Howard Pyle’s Book of Pirates contains vivid illustrations alongside rollicking stories of life on the high seas. Historians have dismissed much of it as romanticized exaggeration, but his depiction of Port Royal still rings true:
[T]he town of Port Royal … in the year 1665 … came all the pirates and buccaneers … and men shouted and swore and gambled, and poured out money like water, and then maybe wound up their merrymaking by dying of fever. … Everywhere you might behold a multitude of painted women … and pirates, gaudy with red scarfs and gold braid and all sorts of odds and ends of foolish finery, all fighting and gambling and bartering for that ill-gotten treasure of the be-robbed Spaniard.
The English captured Jamaica from the Spanish in 1655. They noticed the port’s strategic potential at the entrance to Kingston Harbour and set about strengthening its defenses. Bristling with fortifications, the harbor was expanded to accommodate ships. Traders flocked to the protected haven. But in addition to legitimate trade, the port’s prosperity also derived from less salubrious endeavors: piracy.