Home Ports: The Best Bay

Pensacola, Florida, is now a booming community with a split personality. Hard working port on the one hand, it is also the playground of the idle who have time for golfing, yachting, and spring breaks on the beach. It may even be the haunt of a phantom or two. The long history of Pensacola, not surprisingly, is more about the port than the playground. And both pirates and privateers figure prominently in that mix.


The area surrounding what is now known as Pensacola Bay was populated for thousands of years by Native American groups who subsisted largely off the water, building dug out canoes and fishing in the bay. By the time the first European explorers arrived, the dominant group called themselves the Panzacola and eventually gave their name to the area.

The first explorers to poke around Pensacola were all Spanish. Visits from Ponce de Leon in 1513 and Hernando de Soto about thirty years later established that the area had potential for colonization. It wasn’t until 1559 that Tristan de Luna brought a group of close to 1,500 settlers to the bay from Vera Cruz in Mexico. The pilgrims arrived in August and barely had time to set up a makeshift camp before a hurricane blew through on September 19. It is estimated that a good half of the potential colonists were killed. Some people immediately left for the Carolinas while others tried to make a go of it on the island they called Santa Elena. Lack of fresh water and simmering tropical heat took their toll. Fifty remaining colonists returned to Vera Cruz two years later to the utter dismay of Mexico’s Viceroy.

The French exploration of what would become Louisiana brought Spanish attention back to western Florida. On the hunt for La Salle’s French explorers in the Gulf of Mexico, Juan Enriquez Barroto and Antonio Romero visited Pensacola in 1686. On the expedition was Juan Jordan de Reina, an amateur naturalist and all-pro exaggerator, who described the area as a lush tropical paradise where fruit dripped from trees, game was plentiful and the bay was “… the best I have ever seen in my life.” De Reina’s assessment highly influenced the Mexican Viceroy, Don Silva y Mendoza, to fund another colonial undertaking to Pensacola.

By 1700, a new colony had been established under the governorship of Andres de Arriola. This time the bay was christened Bahia Santa Maria de Galve (after the Viceroy, who was also the Count of Galve) and the land around it began to be known as Panzacola. Much to everyone’s dismay, the soil turned out to be almost useless for growing food stuffs, the area wildlife was hostile, yellow fever and malaria hung over the place every summer and hurricanes continued to wreak havoc. The settlement persevered, however, mostly in response to the growing numbers of French colonists in Mobile, Baton Rouge and New Orleans.

The area slowly urbanized with the Spanish building forts on the mainland. Money became available and with it came smuggling. British and American colonial pirate ships began to appear in the bay, exchanging prize goods for hard Spanish gold or silver. Famous names like Edward Teach and Edward England were known on the waterfront, much to the dismay of Governor Arriola. Raiding by the British and the Creeks during Queen Anne’s War, which took up a little more than the first decade of the 18th century, broke the settlement’s infrastructure down and soon Pensacola was hanging on for dear life.

The French took the settlement from the Spanish some time in 1719, but they could not hold it capably and it returned to Spanish hands. During the French period, the incidents of pirate interaction with local smugglers increased. Only a lack of organization kept early 18th century Pensacola from mirroring the future operation of the Laffite brothers in Barataria.

The French and Indian War brought British rule in 1763 and the area began to prosper. Cotton planting was stepped up, more building took place and Britain hoped to make Pensacola a new Jamaica. Those hopes were dashed with the Revolutionary War. After losing the Battle of Pensacola in 1781, Britain returned the area to the Spanish.

Despite controlling all of Florida and the vast Louisiana territory, Spain’s colonial grip loosened as her troubles mounted in Europe.

Napoleon sold Louisiana to Jefferson; by 1812 much of what had been Spain was the U.S. Andrew Jackson harassed the Spanish with raids on Pensacola and the chaos created opportunities for a new breed of free booters: the privateers. Pierre Laffite probably began the slave trading that would serve him and his brother so well in Pensacola during the first decade of the 19th century. Louis Aury briefly used the bay as a base. Dominique Youx may have considered settling there later in life. According to William C. Davis, Renato Beluche stopped in to the bay just as Britain was amassing warships in preparation for their invasion of New Orleans in late 1814. Beluche may very well have written a letter to the Laffite brothers warning them of the coming storm.

By the 1820s, Florida was U.S. soil. Andrew Jackson briefly took up residence at Pensacola as the area’s first Territorial Governor. By the mid-20s, a Navy Yard was established. Pensacola was used as a supply port for David Porter’s pirate hunting Mosquito Fleet based on Thompson’s Island (now Key West). The worm had turned completely; the frontier town that once welcomed pirates became the urban center that supplied the machinery for their downfall. Hard work at the docks and on the plantations funded gracious living for the wealthy.

As an aside, another seafaring point of interest is the Pensacola Lighthouse. Originally built in 1826 it was first kept by Jeremiah and Micheala Ingraham. Jeremiah died under mysterious circumstances (rumor has it Micheala killed him) and his wife was appointed keeper, a job she did faithfully for fifteen years. When the lighthouse was rebuilt in 1859, a violent haunting began to manifest including objects flying across rooms and unexplained stains on floors. The lighthouse, which is still kept by the Coast Guard, is said to be inhabited by Micheala Ingraham who is angered and offended by the disturbance to her former home. The Coasties say it’s all bologna, but the tourists flock to the sunset tours nonetheless.

Doubtless Pensacola is haunted by more that just the lighthouse keeper’s wife considering all that has happened there. But the locals, and the tourists, probably don’t pay much more attention than the occasional ghost story will rouse. The best bay continues to work and play hard, just as it always has.

Header: Map of Pensacola Bay c 1763 via Wikimedia

Home Ports: Saint Mary's Island

Just north and east of the island of Madagascar is a small group of islets that are perfectly situated. Perfectly, that is, for a pirate looking to score some of the fattest prices in the 18th century world. The islets sit on the edge of the Indian Ocean and just south of the Red Sea and the Gulf of Persia. Using any of them as a port, a clever pirate could take a fat East Indiaman returning to England or Holland one evening and then cruise north the following day to snatch the treasure galley of some Ottoman pasha. All this and home in time for supper. Or so the rumors that circulated in places like the West Indies and the Guinea coast said.

Ile Sainte-Marie is the largest islet of the group in question. As piracy became a target of aggressive persecution by the various European powers in the early 18th century, the men who plied the sweet trade turned their eyes to the wealth of the East and set sail for Africa. They found Sainte-Mary quite to their liking. Not only was it abundant in fruits and game, its native people were friendly – particularly when they found that most of the pirates had not come to enslave them – and the island was surrounded by shallow cays and inlets. These were perfect for hiding from aggressors, evaluating a prize or simply pulling a ship up on her keel and giving her a good careening. It seems, at least on the face of it, a veritable pirate paradise.

This idea caught the imagination of European writers and one in particular, the man who fancied himself Captain Charles Johnson, devoted a good deal of paper to writings on the piratical community he call Libertalia. Johnson, the author of A General History of Pyrates, has come down to us as either an eye witness authority on piracy or a complete crank. It just depends on who is commenting on his work. The idea of Libertalia, which is often reputed to have been based on Ile Sainte-Marie, has caught the imagination of many moderns because of its very modern take on community. Whether or not it actually existed is the point that must be questioned.

Libertalia according to Johnson’s book was the brainchild of a merchant seaman turned pirate named James Misson. In his vision, which was spurred on by his association with a “lewd Priest” from Rome named Giacomo Caraccioli, the Frenchman saw all men as brothers, no organized religion as valid, and slavery as the cruelest of human ills. His pirate utopia was established under a white flag and Libertalia’s motto was “For God and Liberty”. The pirates cruising out of Ile Saint-Marie called themselves Liberi and shared all goods and prizes in common. They routinely set any slaves they came upon free and so their numbers were increased rapidly by the grateful Africans joining up right away. According to Johnson’s description, Libertalia lasted 25 years and welcomed such famous and infamous captains as Thomas Tew, Christopher Condent, Henry Avery and William Kidd. The end of Libertalia is as egalitarian as its founding was revolutionary. Eventually the pirates grew weary of their lives at sea and settled down with the local girls to farm land where “… no hedge bounded any particular man’s property…” and the fruits of their labors were “… carried into the Common Treasury”.

No one would deny that the idea of Libertalia is delightful. Of course, we would all like to imagine the lion lying down with the lamb and beating swords into plowshares. The reality, however, is that Johnson chose unwisely in his fantasy populace. Pirates, though in many ways more democratic than the societies they preyed upon, were also ruthless brigands who were far from altruistic. Slaves were more often than not prizes to be sold, other pirate crews could be a threat to the amount of loot each individual might get, and the last thing these sailors were cut out for was farming. In many cases, getting away from the drudgery of agriculture was why they went to sea in the first place. Then, too, there’s the harsh fact that to take a prize or prizes, some killing will probably have to be done and that seems a poor way to treat a brother.

Ile Sainte-Marie was certainly a pirate base during the heyday of the “pirate round” from approximately 1690 to 1725. There can be no doubt that men like Tew, Edward England, Avery and Kidd at least touched at the island and several shipwrecks dating from the era have been found in the waters around Sainte-Marie. One in particular, sunk in Baie des Forbans not far from the island’s capital, is thought by the explorer Barry Clifford (of Whydah fame) to be Christopher Condent’s Flying Dragon. There is also the old cemetery that overlooks the bay (pictured above) known as le Cimitere des Pirates where modern residents continue to leave offerings for their freebooting ancestors. That seems to me a far more factual legacy than any pirate utopia could ever be.

Tools Of The Trade: The Big Score

Yesterday we spoke of “Long Ben” and his enormous treasure ripped from the Grand Moghul’s ship Ganj-i-Sawai. But Henry Avery was not the only pirate to profit in the extreme from prizes in the Red Sea and Indian Ocean. Here, courtesy of The Wordsworth Dictionary of Pirates, is a surprising list of enormous booty taken by ships from 1690 to 1725 that worked the same round as modern Somali pirates. The new kids only wish they could do so well.

First, Avery himself, whose booty in jewels, gold and silver taken in his 40 gun ship Fancy amounted to approximately 105 million in modern dollars.

Dirk Chivers commanding Soldado and Robert Culliford commanding Mocha took Great Mohammed in the Red Sea in 1698. The total haul was in cash amounting to about $190,000.

John Bowen in Speaker raided what may have been an Indian Pilgrim vessel off Arabia in 1700 and came away with $175,000. In 1703, while working with Thomas Howard in command of Speedy Return, Bowen took two Arabs in the Red Sea for a total prize of $100,000.

Edmund Condent (sometimes called Christopher Condent, although the two pirates may be different people all together) sailing in the Flying Dragon in 1720 brought down an Arab merchant carrying specie, silk, spices and opium to the tune of $200,000.

Also in 1720, the unfortunate Edward England took the East Indiaman Cassandra with his Fancy and Victory, netting about $100,000. The prize was taken not far from the port of Johanna, Madagascar and not long before England’s crew dumped him to beg in the streets of that same port.

Finally, in one of the last great strikes in and around the Indian Ocean, John Taylor in Cassandro in consort with former buccaneer Olivier La Bouche in Victoire took the Portuguese treasure galleon Nostra Senhora de Cabo in 1721. The total prize, including a large chest of diamonds along with other salable goods may have amounted to nearly 100 million dollars.

For those brave, or crazy, enough the money was good. When the Royal, French and later the American navies cracked down and began a system of escorts for merchants in and around India and Arabia, the well dried up. But the prizes are still spoken of, often with awe. Most of us could find a lot to do with our share of a million dollars.

People: The Welsh Pirate

Howell Davis was most probably born toward the end of the 17th century somewhere on the coast of Wales. He is frequently referred to as "The Welsh Pirate" in short biographical snippets on blogs and in books. This always elicits a chuckle from your humble hostess because Davis, as fascinating as his story is, can hardly be consider The Welsh pirate. There were scores of freebooters from the rugged land of Wales, first of all. Second - and perhaps more importantly - when the debate gets heated it has to come down to two very familiar names: Henry Morgan of buccaneering fame or Bartholomew Roberts, the most successful pirate of the Golden Age. But wait; maybe there's a tie-in after all...

By 1718, Davis was serving as Lieutenant on the British slaver Cadogan when she was taken off the West African coast by our old friend Edward England. England had the Captain and any crewmen who did not care to sign on with him killed. Davis was one of the men who decided to turn pirate. He evidently impressed England because, after the slaves were sold and the booty was shared out, Davis was given command of Cadogan.

Davis headed for Brazil but his crew had other ideas. They steered the ship to Barbados where they betrayed Davis, telling dockside authorities who boarded to inspect the ship that their Captain had forced them into piracy. Davis was jailed in Barbados but eventually released when none of his turn-coat crew showed up to testify.

Hoping to continue in the pirate profession, Davis took passage to New Providence but arrived too late. New Governor Woodes Rogers was already sweeping the former pirate den clean. Nothing if not persistent, Davis boarded the former pirate sloop Buck bound for Jamaica. En route, he managed to talk the crew into returning to their former piratical adventures. Davis was elected Captain and Buck made her new base in Cuba.

Davis and his men quickly took two French warships, using ruses both times to avoid injury to vessels or men. Davis appears to have been both crafty and charming and he virtually talked his way onto a prize rather than waisting time with messy cannon fire and boarding actions. His men looted the French ships, goods aboard were sold in Cuba, and then Buck headed across the Atlantic to the rich hunting ground off West Africa.

Buck and her Captain had a deal of success in African waters. When things got tight, especially close to shore when a refit or supplies were needed, Davis had no trouble convincing authorities that we was a legitimate English privateer. He managed to get a larger, heavier gunned flagship which he renamed Saint James by using his smooth talk on a local Portuguese governor. Further up the coast, he convinced the Governor of a Royal African Company slaving fort that he was a pirate hunter. Invited to dine aboard Saint James, the Governor realized the ruse too late. He was held until the Company paid Davis a substantial ransom.

Now at the height of his game, Davis found a protege in Bartholomew Roberts who had been a mate aboard a slaver captured by Saint James. Roberts was with Davis as he and the French pirate La Bouche went on a joint cruise. They took several slavers, including a ship that would become Davis' new flagship, Rover.

The word got out that there was a charming pirate passing himself off as a British privateer and authorities up and down the African coast became more suspicious. When Rover put in at Principe, off the coast Guinea, the Portuguese Governor was ready for his shenanigans. Smiling to his face as if he believed Davis' pirate hunter story, the Governor gave Davis open access to his city. Treachery was afoot, though. Davis and a group of his men were ambushed and brutally slaughtered by the Governor's men while away from their ship.

When word of the butchery got back to Rover, Davis' remaining crewmen elected Roberts Captain. Roberts took the well gunned ships captured by his mentor and bombarded the town with cannon in revenge. He then sailed off into history to use every trick he had learned from Davis.

Howell Davis was certainly an intelligent man who was able to appear comfortable in any situation or company. His brutal end was probably inevitable. But then that seems to be the case with most freebooters Welsh or not.

Pathetic Pirates: Bad Company and Good Intentions

Today's entry under the Double P title is not as pathetic as some of our previous guests. He seems like a diligent sort, brave under fire and capable of command. All the same he ended up far worse than many less famous than himself. His two fatal flaws - neither of which might have bothered him much in another profession - were being a bad judge of character and lacking natural cruelty. And so, a brief look at the life of Edward Seegar known as pirate Captain Edward England.

Born some time around 1700 and probably in Ireland, Edward Seegar joined aboard a merchant ship as a young man. Like so many others whose stories will never be told, Edward was just doing his duty when his ship was taken by pirates. In 1717, Captain Christopher Winter captured the merchant vessel in question and took it back to New Providence, Bahamas as prize. It seems that Seegar voluntarily joined up with Winter and then changed his last name to England.

England crewed with Winter until that fateful August in 1718 when Woodes Rogers showed up and kicked the pirates out of their base on New Providence. England, perhaps seeing an opportunity in the chaos, took a prize sloop with a small crew and became Captain. Shrewdly seeing that the Caribbean would be crowded with displaced pirates, England set out for the west coast of Africa to plunder the rich slave trade.

The new Captain cruised the African coast for some months and took several prizes. He began to amass a small fleet as he went along, always moving to a larger and more heavily gunned flagship as he captured them. Eventually he headed south and rounded the Cape of Good Hope, intending to begin plundering the merchant fleets in the Indian Ocean.

By now, England had given a captured sloop - Victory - to a man he thought he could trust, John Taylor. The two Captains put in at Madagascar for victuals and the careening of their ships. Some surviving documentation of their extended visit recalls that they partied hard with the spoils of their hunting and "...[made] free with the Negroe women." Good times, evidently. But not for long.

Back at sea, England's little flotilla captured his new flagship Fancy of 34 guns. She was certainly a frigate and therefor unusually large for a pirate ship. Taylor moved into England's former ship, Pearl, and the hunting continued. In August of 1720, England and his boys ran into three East India merchants off Johanna Island, north and west of Madagascar. Two of the ships chose to run but the largest and best armed, Cassandra, stood her ground.

While Taylor gave chase to the other ships, the fighting between Fancy and Cassandra was brutal and bloody. The ships exchanged broadside for broadside at close range. Hours later, Cassandra was forced to limp off to Johanna where her Captain, James MacCray (or Macrae) beached her and off loaded those of his crew that survived. Cassandra suffered 37 dead and Fancy lost upwards of 85 men.

While MacCray hid in the jungle, England's men ransacked Cassandra. Goods inside were estimated at a worth of 70,000 English pounds but the magnitude of the prize did not quell the blood lust of the pirates. Some of Fancy's crew grumbled about revenge for their lost mates.

By the time MacCray and his men were forced to reveal themselves for lack of fresh water, Taylor had returned. England took the merchant crew as prisoners and Taylor suggested death for one and all. England put his foot down and, as commander, allowed MacCray to leave the island with his remaining crew. This set Taylor's teeth on edge and he began to suggest mutiny to England's pirates.

It didn't take long for the men to be convinced. England and three others still loyal to him were marooned on a small island not far from Madagascar. Somehow the men managed to make it to the pirate port on the larger island but the damage had already been done. His spirit broken, England was reduced to begging on the streets at Madagascar. In 1721 he died, either of some illness or outright starvation.

Edward Seegar England appears to have been a thoughtful, intelligent and inappropriately kind hearted man who simply couldn't pick a trustworthy second in command. Unfortunately, his shortcomings in the pursuit of pirate glory eventually made him pay the ultimate price.