Pathetic Pirates: Maybe The Trade Isn't For You

I have a sneaking suspicion that the star of today's post would have much preferred that I pick someone else to go first. Its probably like that feeling in middle school when you have to give a speech and you want the teacher to call any name that isn't yours. And then it is your name that rings through the air and damn! Shamble to the head of the class and hope for the best. Sorry, Bart, but your up.

Today begins a new feature here at Triple P: Pathetic Pirates. There's a tendency to imagine the historical freebooters as rough and ready and just ahead of the law. At the very least we think of them dying with fortitude on the deck of a ship or at the end of a rope. But, just like every other profession, piracy has its share of Milton Wademses, ineffectually asking for their stapler and their paycheck, metaphorically speaking. So lets kick off our occasional discussions of the less than adept buccaneers with the sad career of Bartolomeo el Portugues.

Bart's early history is a mystery. I cannot find any mention of him before 1655 when he turns up in Port Royal, Jamaica. Given that this was the age of buccaneers, it is entirely possible that Bart had been an indentured servant somewhere in the Caribbean and then made his way to the infamous pirate haven seeking his fortune, but that is purely speculation on my part. At any rate he was keen to get in on the pirate action and he signed aboard a ship heading for the Gulf and Mexico.

Eventually, Bart managed to get his own small sloop and round up a crew of thirty or so men. They cruised the waters around Jamaica and Cuba, hunting for Spanish merchants. Bart got lucky and spotted a ship laden with cocoa beans and chests of silver coin. The merchant chose to fight and, though ultimately victorious, Bart lost something like half his crew in the melee. He put the prize's crew on his sloop and headed back to Jamaica in the merchant vessel. The weather turned ugly, and Bart was forced to turn his new ship toward Cuba. Here, he ran into three Spanish frigates that captured he and his crew and took them to Campeche in Mexico to be hanged.

Bart and his remaining men were held aboard one of the frigates while the gallows for their execution were being built. At some point, they managed to escape and the story goes that, though he couldn't swim, Bart made "water wings" out of two big jars emptied of their contents. He and his crew made it to land and then walked across the Yucatan peninsula (no kidding!) and managed to hitch a ride on another buccaneer's vessel. This may very well have been the luckiest point in Bartolomeo's life.

Returning to Port Royal, Bart plotted revenge on the Spaniards who had taken "his" wealth. He managed to score a canoe and twenty guys and headed back to Campeche where he once again attempted to take a Spanish merchant. This didn't work out so he returned to Port Royal. He somehow got another ship and went back out but was wrecked on an island off southern Cuba after taking a prize. He made it back to Port Royal once again, this time in one of his ship's boats.

At this point, specifics about Bart's career drop off. I imagine that might be simply because every attempt ends the same way: in disaster. Alexander Exquemelin, a former buccaneer whose book "The Buccaneers in the Indies" gives us most of our knowledge about Bartolomeo el Portugues, closes out his segment on the unfortunate pirate with a literary shake of the head. "He made many violent attacks on the Spaniards without gaining much profit from marauding, for I saw him dying in the greatest wretchedness in the world."

It seems that Bart was so unlucky that he couldn't even die quickly. I hope he, at the very least, rests in peace. Happy Friday, Brethren! See you tomorrow for Sailor Mouth Saturday!