Captain William Trader Jackbiographies, Captain William Trader Jack 1:04 π.μ.
Physical characteristics: Trader Jack was over six feet tall, muscular, broad of shoulder and narrow of hip, with the carriage of the trained fighting man. He had a long scar that ran the length of his face. Handsome, his features were regular, and clear cut with long dark hair and a black beard. Piercing dark blue eyes.
Early Life: Much of his early life was never known. Some have said that he was the child of a Spanish nobleman and a peasant girl. He joined the Naval Academy and went on to become a well-respected Commander of a privateer. By the age of 27 he was an Admiral and naval attaché to the king of Spain. Some say he was actually a mercenary backed by the Spanish government and several New World investors to track down pirates and reclaim their stolen wares.
How he became a pirate: Instead of being acclaimed a national hero, a jealous member of the Royal family accused him of becoming a pirate. Charges of theft were soon invented against him and his arrest was authorized. So Trader Jack commandeered a ship and sailed for the Americas and a life of piracy. Soon towns all over New England would each have their own tale of Trader Jack secreting his treasures in the darkness of night.
His main territory: Cape Cod and the island of Martha’s Vineyard. The waters off the coast of New England down the North American coastline to the Florida peninsula.
Famous/Infamous for: Martha’s Vineyard was home to many buccaneers and fishermen, but Trader Jack organized them into a company of privateers and smugglers. He built houses, cottages, warehouses, and stockades that held slaves awaiting auction, a cafe, gambling den, and brothel. His men numbered over a thousand; some came from many countries, and included navigators, gunners, carpenters, cooks, sail makers and riggers. They plundered cargoes of ships for slaves, silks, spices, jewels, furniture, household goods, art, food, and medicines. His fleet consisted of Martha’s Revenge and three other ships as well, the Alabama, the Shenandoah and a tender, which served the three fighting ships. He operated a vast smuggling network in and around Cape Cod and the islands for over twenty years. Many called him a pirate, others called him a friend, after his ship's famous battle with the more heavily gunned British frigate Endymion, and they all called him hero.
Notable battles: No name was given to this battle with the more heavily gunned British frigate Endymion, off the southeastern tip of Martha's Vineyard. Some have called it The Battle of Noepe.
Finally met his end: In the spring of 1822, on the very day Trader Jack and his crew were to begin dividing up the booty amassed during 38 years of pirating together a rich merchantman was seen, and the opportunity for one last prize just seemed too good to miss. Trader Jack and his crew put to sea in pursuit of the prize, but coming within range, they were shocked when she hoisted the flag of the US Navy and ran out her cannons. A fierce battle ensued; the American cannonballs repeatedly punctured the hull of Trader Jack’s flagship, while still more shattered her masts. Martha’s Revenge was sinking as the frigate USS Potomac approached to finish the job. Realizing he could not win it, Trader Jack wrapped himself in his anchor chain and leapt to Davy Jones' locker in the depths of the Atlantic, off the island of Martha’s Vineyard. The rest of his crew were either killed in the battle or were captured and tried as pirates, later to be executed.
Biggest myths: Trader Jack is said to have more than a dozen wives scattered from the coast of Maine down to Florida. It was also rumored that he had a wife and son who had been educated at Harvard, living in Boston, though the truth of his early life was never known.
The Story of Trader Jack
The romantic age of the Vineyard is past, the days when pirate bands preyed upon the peaceful merchantman, stole his goods, and carried away his women passengers, have gone, but romance still holds sway in the minds of each of us, and in the pirate Captain William Trader Jack we find a story that is full of the spice of romantic adventure, that abounds with thrills, and causes the pulse to beat just a little faster at some daring exploit, the eyes to fill with water at some touching story, or the fists to clench in the good American way at the brutal butcheries that authentic documents show were committed. Trader Jack has gone, his pirate gold lies hidden somewhere on the isle of Martha’s Vineyard, but the bleached bones of his murdered victims, with the stories that have drifted down from past generations, give to the world a synopsis of the life and death of Trader Jack, the terror of the New England Seas.
Born near Seville, Spain in 1756, his name was William Trader Jack. In 1774, at the age of 18, he was arrested for running away with his young lover (kidnapping a young girl who was pregnant with his child) and given the choice of joining the Naval Academy or going to prison. Unsurprisingly William Trader Jack chose the Navy. Before gaining his reputation as a pirate though, he was a well-respected Commander of a privateer. Known for his skill and bravery as a Captain, he later was commissioned to fight a war against the pirates that haunted the Atlantic. By the age of 27 he was a naval attaché to King Charles III's court. Some records give him the honor of being what we would call an admiral. Jack was also an officer of high standing in the naval affairs of the Spaniards. Jack's romantic intrigues at the court were worthy of Don Juan himself until he spurned the advances of a member of the Royal family. From this point on it wasn’t long before he was accused of becoming a pirate himself. Charges of theft, that he filched the crown jewels, were invented against him and his arrest was authorized. So Trader Jack deserted his wife and children, gathered together a nice lot of cutthroats, stole the prize vessel of the Spanish fleet, he later renamed Martha’s Revenge, and sailed for the Americas and a life of piracy. This happened in the year 1782. A price was declared upon his head, and it is stated, when Trader Jack heard this decree, he swore eternal vengeance upon all Spaniards in general, and commenced to destroy the commerce of Spain
Trader Jack was one of the most revered and feared pirates that lurked around New England. His career of piracy began and ended in Massachusetts. Towns all over New England each have their own tale of Trader Jack secreting his treasures in the darkness of night. Between 1783 and 1821 Trader Jack captured over 400 ships from the coast of Maine to the Florida peninsula, making him one of the most successful pirates of all time.
He showed no mercy in battle, killed all passengers and crew, with the exception of beautiful women (whom he made concubines). He sometimes took wealthy people prisoner for ransom, holding them at Captiva Island (some claim that this is how the island got its name). From time to time, Trader Jack could be found pirating in the company of other pirates, including the famous Jean Lafitte, Long John Silver, Billy Bones, and Black Caesar also known as the Black Dog. Some writers have said that Trader Jack joined Blackbeard, who mastered the psychology of terror and made sailors shiver and surrender at the sound of his name, while others have stated on good authority that Blackbeard joined Trader Jack’s band, contributing a boat and thirty men.
Cape Cod and the island of Martha’s Vineyard at that time being a rendezvous for pirate fleets, Trader Jack settled in Oak Bluffs Harbor and built upon the shores of what is now called Cottage City, thirty houses, where, under guard, his female captives were placed, all male prisoners being killed when captured. The buildings were constructed of ship’s beams, and arranged in a semi-circle close to the water’s edge.
About one hundred yards farther inland an burying ground was discovered, containing not only the bones of his men, but the skeletons of his murdered women captives. Many a touching story has been unearthed when the ghostly remains were uncovered. Stories of great strong men who died in the fight, of women who died to save their honor, and of nobility we even find a trace, but these are only traditions.
Located at the center of Cottage City lies a burial mound fifty feet high and four hundred feet in circumference at the base, built centuries earlier, it is thought, by the Vikings. Excavations in this mound have produced ornaments of gold and silver, together with hundreds of human skeletons. On its summit Trader Jack constructed an observation tower, the Trinity Park Tabernacle now stands in it’s place, where always a grim sentinel was stationed and looked across the warm, smiling waters off the island of Martha’s Vineyard.
The present island of Martha’s Vineyard, the pirate named after his lovely bride Martha, also known as The Little Spanish Princess. Taking the best of everything when a capture was made, he chose the best of the islands in Oak Bluffs for his own secret haunts. It is said that Trader Jack was saluted the King of the Pirates, and his home on the island of Martha’s Vineyard was regal in its fittings.
While taking the census of 1900 two gentlemen stopped at Vineyard Haven and spent the night with Samuel Bellamy. The race of the old buccaneer was nearly run, but all through that night he told a story of piracy that could scarce be believed, yet it was a dying man that was clearing his soul before his Maker. He told of the looting of ships, the massacre of innocents, and last of all, when his life had nearly passed, he told the story of “The Little Spanish Princess”. He told where the body would be found, and a sketch was prepared under his direction, and in recent years in the exact location as described the skeleton of a beheaded woman was found. This is the story.
In the early days of the year 1801, a princess of Spain sailed in great state for Mexico. While in that country she was royally entertained by its Ruler, and to show her appreciation to the Mexican people she prevailed upon the nobles to allow her to take eleven of Mexico’s fairest daughters away with her to be educated in Spanish customs. A treasure of much gold, bound in chests of copper, it is said, was in cargo. When about forty miles from what is now Boca Grande, Trader Jack engaged them in combat, killed the crew, took the gold, and carried away as captives the princess and the eleven Mexican girls. The princess he kept for himself, the maids were divided among his men. The little Spanish princess spurned the one-time favorite of the King, and Trader Jack swore that if she did not return of her own free will the affections lavished upon her, she would be beheaded, and the story goes the threat of Trader Jack was fulfilled. Far away from her native land, alone on a tropical isle, the little princess still lies in the lonely bed made for her by Trader Jack. The night birds sing in the dusk and lull her spirit to rest in the evening, and the moon throws kindly shadows o’er the spot where royalty sleeps.
From members of Trader Jack’s crew many a strange story has drifted down concerning him, his traits, his ways, and his passions. He was polished in his manners and a great lover of fashionable clothes; fearless in fight, and at all times cruel in his nature. Concerning women he was fanatical, and his houses were always filled with captives. It is stated beauty was essential with him. He kept for himself a certain number of picked beauties, but so fickle was his nature that when an additional capture was made and a new face appealed to him, one of his old loves must forfeit her life to make room for the new favorite. That this was true there is no doubt, as the graveyard of Trader Jack tells its own terrible story.
By 1821 Trader Jack was 65 years old and ready to retire. The Florida peninsula and the North American coastline were now in American hands, and there had been a determined and unrelenting effort by the US Navy to destroy the pirates that preyed in their waters. In October 1821 the USS Potomac captured 4 pirate ships in the waters off of New England. The war on piracy becoming too severe, so it seemed like a good time for Trader Jack to hang up his cutlass. That December, Trader Jack announced his retirement to his crew. Trader Jack and his crew agreed to divide their wealth, which was then estimated at thirty million dollars, to give up piracy, and live as honest men the rest of their lives. This was decided upon and plans made accordingly.
In the spring of 1822, on the very day they were to begin dividing up the booty amassed during 38 years of pirating together, which at that time was hidden in six separate hiding places, he cited what appeared to be a large English merchantman just off the island of Martha’s Vineyard. It is said his greedy eyes lit with pleasure at the thoughts of just one more victim before his piratical days were over.
Closely following the shoreline, they crept around the island of Martha’s Vineyard and slipped into Oaks Bluff Harbor through what is now known as Little Trader Jack Pass, and gathered together his crew. Great excitement reigned when the plans were unfolded. The band of eighty men was divided into two parts, he commanding thirty-five men, Billy Bones thirty-five, while ten were left in charge of the camp. At about four in the afternoon Trader Jack and his crew put to sea in pursuit of the prize. His men dashed through Little Trader Jack Pass for the English prize; fast overtaking the fleeing ship, the black flag was hoisted, and his men stood ready with the grappling hooks, but coming within range, they were shocked when suddenly the English flag floated down and the Stars and Stripe pulled in place and ran out her cannons. The helpless merchantman was no other than the war vessel USS Potomac! In a moment guns were uncovered on deck, a fierce battle ensued, the American cannonballs, repeatedly punctured the hull of Martha’s Revenge, while still more shattered her masts. Martha’s Revenge was sinking, as the USS Potomac approached to finish the job and Trader Jack realizing he could not win it, his boat disabled by the shots from the war vessel and capture staring him in the face, he wrapped a piece of anchor chain around his waist and leapt to Davy Jones' locker in the depths of the Atlantic, off the island of Martha’s Vineyard. His age at his death was about sixty-five. The rest of his crew were either killed in the battle or were captured and tried as pirates, later to be hanged at the yardarms, with the exception of the cabin boy and the ten men left in charge of the captives, they having escaped to the mainland. Samuel Bellamy was in this gang. The cabin boy was carried to Boston, where he remained for many years.
Watching from the shore were Billy Bones and a handful of men who, seeing the end of their comrades, turned and fled, and then packed up the treasure of many years which had been loaded into twenty large chests, filled with gold and jewels and buried it somewhere along the shore of Oak Bluffs, a booty reputed to be worth $30 million. The next morning Billy Bones’ boat was captured, set a fire and sunk off the coast of the island of Martha’s Vineyard. Whether he was captured at this point is not known, as so many conflicting stories arose concerning him, still it is a positive fact that he was buried on Martha’s Vineyard.
For thirty years the craft of Trader Jack, Martha’s Revenge, was visible from Cape Cod and the island of Martha’s Vineyard, lying five miles off Oak Bluffs Harbor, but the sand has now completely covered the wreck.
The treasure of Trader Jack still lies unmoved. The bones of the bold buccaneer, with his pirate ship, have vanished, but legends from the vineyarders say that some times in the dead of night, off the Island of Martha’s Vineyard, when the waves are singing a lullaby to the weary and the wind is whispering soft messages through the pine trees/palmettos, the phantom fleets of the pirate crew arise from their ocean resting places and pursue, as in days of old, the ghost ships of the merchantmen.
Who really knows? If you see something odd sticking out of the sands of Martha’s Vineyard, take a closer look, it just might belong to the most famous pirate ever, Captain William Trader Jack.