Alexander Exquemelin, who first published his Buccaneers of America in 1678, is a ton of fun to read. His prose is delightfully fresh and some of his vignettes have become legendary. Whether or not all of them are true and accurate is a point still debated among scholars who study piracy but, to my way of thinking, that's not the point. I'm fairly certain in my own mind that at some point some freebooter did something at least very similar to what Exquemelin describes.
A good instance is today's slice of history from the good Doctor's prose. According to Exquemelin our story occurred around 1602 and was the first instance of a Tortugan flibuste raid on a Spanish ship. Most sources say the date is in error and the incident probably took place in the mid-1600s if at all. What is not open to debate is that Pierre le Grand probably was one of the first successful rovers based on the Island of Tortuga.
Pierre le Grand - another shadowy figure in the annals of buccaneers, pirates and privateers - was a merchant in Dieppe, France at some point in the 1600s. Rather romantically, he is said to have lost everything to freebooters and speculation whereupon he pulled up stakes and made his way to Tortuga. He assembled a crew of 30 and headed out into the Caribbean in what was then referred to as a chaloupe - the precursor of the 18th century sloop.
Time dragged on in the small, close packed boat and provisions and water went from low to nonexistent. Desperately, the men scanned the horizon for a ship to raid. As the old sea chanty tells us: "...no purchase no pay" and the men aboard le Grand's chaloupe were quite literally starving for a prize. When things seemed at their most dire, the buccaneers spotted a large Spanish merchant and decided unanimously to take her or die.
They immediately packed on sail and went after the merchant with no pretense as to their intent. The people aboard the Spanish ship could certainly ascertain why the little chaloupe was giving chase but when the situation was reported to the Captain he refused to take it seriously. What cannon the merchant had were stored in her hold and, despite advice to the contrary, the Captain would not have them brought on deck. He acquiesced somewhat by ordering tackle rigged to pull the guns up if necessary, and then retired to his great cabin to play cards with some of his passengers.
Le Grand and his men were not letting up and they eventually came alongside the merchantman. Le Grand, in order to avoid any last minute attempts by his crew to second guess the plan, had his surgeon drill a hole in the hull of the chaloupe. Now it truly was an all or nothing game for the flibustes. Their ship was sinking. Taking the merchant was their only option.
Grabbing every portable armament they had at hand, le Grand and his men boarded the Spaniard. A bloodbath ensued, with everyone who showed any resistance slaughtered. Without much trouble, le Grand made it down to the great cabin where the merchant Captain was still at cards. Leveling a pistol at the Captain, le Grand demanded unconditional surrender. As the sun set and the merchant Captain no doubt contemplated his own foolish hubris, the buccaneers stowed their prisoners in the merchant's hold. Exquemelin notes that the Spaniards grumbled to one another as they went below: "Jesus! They are demons."
The point of the story, as I see it, is that a large ship could be overcome by a much smaller and more poorly armed vessel if the attitudes of both crews were in line. Le Grand and his men needed a prize at any cost and were willing to sacrifice all for it. The Spanish merchant imagined herself impenetrable to such a small force, and took no heed of them until it was way too late. Hollywood broadsides and rope-swinging boarding not withstanding, I've a feeling that the incident Exquemelin described occurred over and over on more than one coast.
So stay a little hungry, Brethren, and keep your eye on the horizon. You never know when that rich merchant that imagines you pose them no threat might appear.