Columbus Day: 17 Days Until Halloween

Today in our Haunted Halloween Countdown we present a legend about the pirate haven of Port Royal, Jamaica, in honor of the island’s discovery by Christopher Columbus.



Peter Painter’s Revenge

Abridged from Outer Banks Tales to Remember
by Judge Charles Harry Whedbee

That Peter Painter actually existed in the late 1600s and early 1700s there can be no doubt. His name does appear in the colonial records of that day. However, it is the gaps in his recorded history that make Mr. Painter fascinating.

People say (and the records agree) that Peter Painter was a pirate, and a very successful one….Painter’s happy hunting ground was the Caribbean Sea, and his home away from home was the notorious pirate town of Port Royal on the island of Jamaica in that sea. This small city was a phenomenon not seen before or since in this hemisphere.

Christopher Columbus discovered the island of Jamaica on the morning of May 3, 1494, and he was greatly impressed with the beauty and charm of the place. He anchored in what was later to be the Port Royal harbor and took possession in the name of the royal government of Spain. From that time the island changed hands a number of times as the unsuccessful Dutch, the frustrated French, and the eventually victorious British all tried in turn to conquer and to hold the verdant land. The English finally solidified their hold in 1655, and the island has been British ever since.

In terms of actual government, however, the pirates took hold of the town of Port Royal and ruled that city for years….

That lovely city became the most wide-open, rip-roaring center of debauchery you could imagine. One reliable report of the time estimated that for every one hundred people in Port Royal, there were at least fifty establishments that sold strong drink. Even then Jamaican rum was famous, and the pirates guzzled it with abandon. Prostitutes were encouraged and were on hand by the hundreds, plying their ancient profession where they chose. Many of them returned to England rich beyond belief after a few years. Public drunkenness was the accepted norm, and fist fights and duels were an everyday occurrence. So long as the pirates paid their bills, they could do just about anything they pleased without let or hindrance….

The chief revenue of this administrative body was a port tax that was imposed on each incoming pirate ship…. It was truly a pirate sanctuary run by pirates for pirates, and it roared with revelry both night and day….

It was in 1692 that Captain Painter returned to this city…No sooner had he gotten into town and gotten drunk than he was clapped into jail on a charge of not paying his port fee. The captain was furious. He knew full well he had paid his entry fee, but he could not find his receipt. Although he was well known in the town and respected among the other pirates, his protests against the new administration were in vain. He was tried quickly and as quickly sentenced to remain in prison until he paid five times the port fee for his vessel.

The visiting pirate might well have stayed in that stinking prison for the rest of his life had not his quartermaster and several of his crew gotten together and sold what remained of their share of the last conquest to raise money to pay him out. As soon as he was out of jail, Captain Painter lost no time in setting sail toward the west.

Once out of the harbor and well away from the island, the outraged captain walked to the rail at the stern of his quarterdeck. Shaking his clenched fist at the city in the distance, he swore an awful pirate oath. The story goes that he actually called on the devil himself and all the evil spirits of the undersea world to avenge his treatment, promising to serve the devil the rest of his days in return.

Even as the crewmen watched in terror, there came an awful rumbling from the very depths of the sea. The ocean became violently agitated with waves running in every direction and colliding with each other in confusion.

Ashore, a violent earthquake shook the island of Jamaica from end to end. Before the eyes of Painter’s crew, the city of Port Royal suddenly sank beneath the sea, lock, stock, and barrel. It just disappeared as though some giant sea creature had swallowed it up. Where the town had been, the turbulent sea was dotted with the struggling figures of men and women drowning. Boats were capsized like so many toys. The whole town was destroyed, and the human survivors were few indeed. A tremendous tidal wave followed the earthquake, but it caught Captain Painter’s ship squarely on her high stern and the vessel somehow managed to ride up and over the huge surge without loss of life. The entire crew escaped to the open sea….

…History records the earthquake and the complete destruction of Port Royal. The folklore of the coastal people to this day describes the event as the pirate’s revenge, and it has been so handed down through the years from generation to generation.


Check back for more tales of terror and legend in our Haunted Halloween Countdown or pick up one of the spooky books they come from.


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