Captain William Kidd – From Privateer to Pirate Hunter to Pirate

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In the world at large, Captain Kidd is regarded as one of the most dreaded pirates in history, often mentioned alongside the likes of Blackbeard and Henry Avery. However, to those who learn his story, William Kidd becomes a much more complex and controversial figure, even a tragic one. It seems that although he chased glory, fame, and fortune, he wanted to do it as a legitimate captain and not as a criminal. He tried to resist crossing that line for as long as he could, but in the face of adversity, great misfortune, and a mutinous crew, Captain Kidd could seemingly turn to the dark side.

William Kidd was born circa 1654 in Dundee, Scotland, to John Kidd and Bessie Bashart. Other places, such as Granac, have tried to claim to be the true birthplace of the infamous Captain Kidd. However, during his trial, Kidd’s own written testimony stated that he was originally from Dundee, so we presume he knew his own place of birth. The city also has a record of a sailor’s pension that his mother received after his father died when he was five years old.

As is the case with most pirates, the early life of William Kidd is pretty obscure. Raised by a widow on a sailor’s pension, he didn’t have many options and needed to find work from an early age. After a few years of basic schooling, it is likely that William Kidd took to the seas just like his father. Consequently, we now enter a black hole regarding his life story and emerge decades later in the mid-1680s when Kidd was already an experienced seaman in his early 30s.

At that point, Kidd made his way to a tiny speck of land off the coast of Hispaniola in the Caribbean, where he met his future companion and arch-nemesis, Robert Calico, a sailor from Cornwall. The duo struck up a friendship as they were both looking for work on a vessel. They found it upon the San Rose, a French privateer captained by Jean Phantal, that came into port to recruit crew. It wasn’t an ideal position, as the crew was predominantly French while Kidd was the only Scottish sailor alongside a dozen or so Englishmen. However, work was scarce at the time since all maritime nations were at peace with each other.

Piracy was always an option, but once you raise the black flag, you can’t go back. Kidd seemed particularly inclined toward life as an outlaw. Privateering was basically legalized piracy, where a ship received a letter of marque from a governor that entitled it to attack and plunder vessels deemed enemies of the state. The downside was that you could only attack approved targets and had to kick back a share of the spoils to the government. However, you didn’t have a noose waiting for you when you got back home, so that was a plus.

Even though things were quiet at the time, there were rumblings of war breaking out between France and the Netherlands. Ultimately, Kidd decided he probably didn’t have to wait for action, so he signed up with the San Rose and went out looking for Dutch merchants. During his voyages, the San Rose ran into a French fleet led by Admiral Jean-Baptiste de Cass. The fleet was looking to cause trouble for the Dutch, so Kidd’s ship joined them as they sailed to Suriname on the northern coast of South America.

On the way there, they stumbled upon a cargo-laden vessel coming from Havana. Just one problem: it was Spanish, not Dutch. Even at the best of times, the line between piracy and privateering can get a little hazy. The French really didn’t want to lose this prize, so they found a loophole. Since the San Rose technically didn’t hold a valid commission, only they would take the capture, while the other ships would simply observe with their cannons pointed at the Spanish vessel. If the plunder was divided equally, it would indeed be a fortuitous series of unexpected events.

And wouldn’t you know it, that was exactly what happened. The crew of the San Rose abandoned their former vessel and upgraded to the faster, better-armored Spanish ship. They continued on to Dutch Guiana to attack the port town, only to discover seven armed Dutch warships sitting in the harbor, eagerly awaiting a little dust-up. The French fleet got walloped pretty badly by cannon fire and sailed away with its mast tucked between its legs.

The fleet was trying to decide its next move when the stunning news reached it: in July 1688, England had declared war on France. In fact, pretty much every European maritime power had done so, triggering the Nine Years’ War, or the War of the Grand Alliance. This created a bit of an awkward situation for William Kidd and the other British crewmen who now found themselves sailing with the enemy. However, the French seemed cool about it, assuming that everyone aboard valued plunder above patriotism and that this new war simply gave them more targets to attack.

This, however, was a miscalculation on the part of the French, as their British crewmen were more loyal to their king and country than expected. Once the war had started, Kidd’s fleet attacked the island of Saint Christophers, jointly owned by the French and the English. They launched a full-scale land assault, leaving behind only a handful of men to watch the ships. On the vessel commanded by Jean Phantal, this included William Kidd and all the English sailors, who generally stuck together.

Once all the land troops were out of sight and the tide was out, Kidd gave the signal to strike. The English crewmen sheathed their daggers and attacked the remaining Frenchmen, who were taken completely by surprise. Throats were cut, and backs were stabbed as the British threw their former comrades in the water and prepared the ship to cast off. Kidd and his men had just stolen a ship from a French fleet and headed for the neighboring British Isle of Nevis, where they received a hero’s welcome and were invited to drink with the governor. It was there that William was introduced for the first time in his life as Captain Kidd.

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Now back to today’s video. It was now official: the ship that Kidd had stolen was renamed the Blessed William, and he was appointed the new captain. The Blessed William joined a small fleet commanded by the local governor, Colonel Christopher Codrington. By Christmas, the fleet was joined by another privateer captain, Edwards, and together with Kidd, they led an assault on the French island of Marie Galante as revenge for the attack on Saint Christopher.

The following year, Kidd locked horns with his former running mates led by De Cass and mounted a successful rescue of some English troops who had been taken prisoner. Hudson was very complimentary of Kidd’s skills in naval warfare, later writing that Kidd was with him in two engagements against the French and fought as well as any man he ever saw. Back in the English Isles, Captain Kidd was hailed a hero and feasted at banquets. It seemed like he was the man of the hour, but there was one group of people who weren’t particularly thrilled with him at that moment: his own men. Fighting for their country was fine and dandy, but only as long as it was rewarded with shiny coins and precious gems. Risking their lives for the English Navy was not something they signed up for, and they made it clear to Kidd that they wanted to go pirating—French, Spanish, Dutch—it didn’t really matter as long as there was booty to be had. Kidd refused, so Calico persuaded the men to mutiny, sailing away on the Blessed William during the night.

All of a sudden, Kidd found himself not only bereft of his ship and crew but also of his share of the plunder when they sacked Marie Galante. He was penniless and shipless, but his reputation was still in good standing in the Caribbean, so Governor Codrington hired him to command one of his privateers in the war with France. After a year of loyal service, Kidd was rewarded with his own ship, a modest 16-gun sloop they captured from the French, which was renamed the Antiguan. Now that he was Captain Kidd again, he could travel at his leisure once more.

His hatred for Calico and the rest of the mutineers still burned in his heart, so when he received word that the Blessed William had been spotted in New York City, he weighed anchor and set sail for revenge. Upon arrival in New York, Kidd discovered that he had missed his former ship by a few months. However, he found himself embroiled in someone else’s conflict. Kidd arrived just in time to take part in the conclusion of a bizarre episode from New York’s early history known as Leisler’s Rebellion. Back in 1689, wealthy Protestant merchant and militia captain Jacob Leisler took over part of the colony by force when he heard that English King James II, who was Catholic, had been deposed by William of Orange, a fellow Protestant. Leisler named himself acting governor, fully expecting to receive the backing of the new King William. However, William wasn’t impressed with his efforts, despite his Protestant pedigree, and instead declared him to be a usurper and ordered that all Leisler’s supporters be arrested and executed.

As it happened, Captain Kidd arrived in New York at the same time as the new governor, Henry Sloughter, and his support troops commanded by Colonel Ingoldsby. As one might expect, Leisler wasn’t in a hurry for a date with the gallows, so he barricaded himself inside the fort. Since Kidd happened to be in the neighborhood and had cannons to spare, the real governor asked him if he wouldn’t mind lending a hand. Kidd accepted, although ultimately it proved unnecessary. Leisler eventually surrendered peacefully, presumably at the insistence of his own weary garrison, who had no interest in fighting their own countrymen just to keep him in power. Leisler was arrested and executed for treason, Sloughter became the new governor of New York, and Captain Kidd was once again hailed as a hero for saving the colony from tyranny.

New York’s wealthy merchants were particularly grateful, and Captain Kidd found himself as the guest of honor at many banquets and social events. At one such function, Kidd made the acquaintance of Sarah Bradley, one of the most beautiful, desirable, and wealthiest widows in town. The captain put his Scottish charms to work, and after just a few months of wooing, the former widow became Sarah Bradley Kidd. The marriage turned William Kidd into one of the richest and most respected men in New York. For the next few years, he was content with living the life of a colonial patrician. He bought some land and a couple of daughters and served as a respectable pillar of the community.

He still kept the Antiguan ready for action since England and France were still at war. Kidd had a privateering commission from the New York governor to attack French ships that got too close to their shores, and he later received a similar commission from Massachusetts. However, this life proved too quaint and too quiet for a man of action like William Kidd, and ultimately he decided that it was time for a career change.

In 1695, Kidd sailed to London hoping to secure a captain’s post with the Royal Navy. This was phenomenally ambitious, even foolhardy. The Navy had a pretty strict promotion system; maybe if you were the son of a lord, you could skip a few steps, but Kidd was the son of a deceased Scottish sailor and, as far as we know, had never served aboard a Royal Navy vessel. Now he was hoping to be made captain of his own ship. This was never going to happen; in fact, Kidd couldn’t even secure a meeting where he could be told no to his face.

But destiny soon provided him with another opportunity. While in London, he ran into some merchant acquaintances from New York who knew a friend who knew some friends, and together they hatched a plan to obtain a privateering commission and a new ship for Kidd to go hunting for pirates and Frenchmen. A man named Robert Livingston orchestrated the whole thing and got some very influential noblemen to fund the construction of one of the most powerful ships prowling the Seven Seas: a three-mast, 32-cannon, 287-ton warship called The Adventure Galley. Captain Kidd even signed a performance bond for twenty thousand pounds, guaranteeing that he would deliver to his backers. Kidd was liable for the money himself, which meant that he could not only lose his fortune but even end up in debtors’ prison. Clearly, he was not lacking in confidence, but in the immortal words of Han Solo, “Great, Kidd, don’t get cocky.”

In April 1696, The Adventure was ready to sail, but not so fast, said Captain Stewart of the HMS Duchess. While navigating the waters of the mouth of the Thames, The Adventure failed to follow proper Royal Navy etiquette of dipping the flag or pulling the canvas out of respect when passing a superior. Stewart was the kind of man who took umbrage at such behavior. Since he wasn’t shown the proper deference, he ordered the Duchess to fire a shot across the bow of The Adventure. Then he came aboard the ship and informed the captain that he would be press-ganging his 30 most experienced sailors into service. This was something that Stewart could do as a Royal Navy captain. Kidd appealed to the Lord Admiral, who eventually ordered Stewart to return the men to The Adventure. But the Navy captain still had the last laugh; although he returned the same number of men, they weren’t the ones he originally press-ganged. Instead, he used the opportunity to unload his 30 laziest and most troublesome sailors on Captain Kidd. Not an auspicious start for Kidd’s career as a pirate hunter, and things were about to get worse.

Kidd had made quite lofty promises and needed to plunder a lot of ships to hold up his end of the bargain. It made sense for The Adventure to sail where the pirates were, so it set course for Madagascar, which was supposed to be one of the trendiest pirate havens of the day. However, by the time Kidd got there, the party was over, and everyone had left. There simply weren’t any targets to be had. On top of this, many men were starting to show signs of scurvy, while The Adventure itself wasn’t faring particularly well since it had been built hastily and on a budget. Kidd had no choice but to dock while his men rested and his vessel was patched up. He then sailed to the nearby Comoros Islands, which served as a stop-off point for ships from the East India Trading Company. Kidd hoped to find a peaceful island where he could careen his ship for extensive repairs. Instead, he encountered a violent storm that further damaged The Adventure and an outbreak of cholera that killed 40 of his men within a week. Other crewmen decided to leave Kidd’s command, and to top it all off, the captain learned from passing ships that rumors were spreading that The Adventure had raised the black flag and turned to piracy.

It was hard to think how things could get any worse for Captain Kidd, but then he also started to deal with the looming threat of mutiny. His men were getting fed up with enduring storms, outbreaks, and months at sea with nothing shiny to show for it. They better find something to plunder soon, or else! Captain Kidd and The Adventure spent 1697 in and around the Indian Ocean, with many of his best men either press-ganged or falling victim to cholera. Kidd had no choice but to replenish his ranks with sailors of dubious reputation. Every now and then, The Adventure did take a prize, but nothing big enough to keep the men happy. With each passing day, Kidd’s crew was getting more and more discontent, and the idea of mutiny became more likely.

On one occasion, after refusing to attack a Dutch merchant because it wasn’t a valid target, the captain got into a loud shouting match with the ship’s gunner, William Moore. In the heat of the moment, Kidd threw a bucket at Moore’s head, fracturing his skull and killing him a day later. But this outburst of violence did little to quell the tensions bubbling beneath the surface. With over two-thirds of his crew wanting to turn pirate, Kidd understood that he couldn’t swim against the current forever. He risked mutiny or even worse, so ultimately Kidd relented and thought maybe it would be just this one time.

To his credit, Kidd picked a hell of a target: a giant Indian trading vessel called the Quadar Merchant. In late 1697, the ship filled its cargo hold with cotton and left Surat in Northwest India, rounding the southern tip before arriving in Bengal. There, it sold its goods and started on the journey home with its coffers full of gold and silver, as well as valuable goods such as silk and muslin. It was certainly an inviting prize that would tempt any self-respecting pirate. On January 30, 1698, The Adventure captured the Quadar Merchant off the southern coast of India. No fighting was necessary; the merchant vessel was traveling with a pass issued by the French East India Company. Kidd was aware of this and raised the French flag, boarding the ship without violence.

The Quadar Merchant was an Indian ship hired by Armenian merchants and captured by an Englishman. Despite this, Kidd hoped that he could argue back home that the fact that it was under French authority made it a valid target. After all, governments back then had a tendency to play dumb whenever a privateer got a little too overzealous. But little did Kidd know that the wind was now blowing in a different direction. For starters, the war was over; England and France were at peace once more and eager to show that they were serious about stamping out piracy. But even more importantly, the Quadar Merchant had ties to the emperor of the Mughal Empire himself, Aurangzeb. Just three years earlier