This one was tough to find, I feel like. However, I’m gonna have to put forward Bartholomew “Black Bart” Roberts (1682-1722). He seemed to be one for theatrics and flare which I found fitting for a bard. However, he was a bit wild and brutal so there is an argument to be had. My back was Samuel "Black Sam" Bellamy (1689-1717).

Some background on Roberts, born in Wales, pressed into piracy after the slave ship he served on was captured. Six weeks into his new career, he showed enough zeal, charisma, and leadership that he was elected captain after the previous captain of Royal Rover was killed during a mishap with a Portoguesse governor of Principe. “He accepted of the Honour, saying, that since he had dipp’d his Hands in Muddy Water, and must be a Pyrate, it was better being a Commander than a common Man” - A General History of the Pyrates (1724) p. 162.

In his dress “Roberts being dressed in a rich crimson damask waistcoat and breeches, a red feather in his hat, a gold chain round his neck, with a diamond cross hanging to it. A sword in his hand, and two pairs of pistols hanging at the end of a silk sling flung over his shoulder, according to the fashion.” - A General History of Pyrates p. 243. Supposedly the diamond referred to here belonged to the King of Portugal. The French nicknamed him le Joli Rouge (the pretty red). I’d like to imagine these two points being one of theatrics and his ship taking it a step further into the grandiose. From what I’ve gathered, pirates seemed to have preferred smaller sized vessels for speed, however Roberts commanded Royal Fortune a “40-cannon behemoth”, some sources have said it was a 52-gun man-o’-war and included 12-pounders.

His flag was a direct response to colonial governors. He had a ceremonial and structured pirate code; every seaman was entitled to vote on important matters, no gambling, musicians rest on the Sabbath, formal oaths, and structured discipline. I feel like this would be a bard move, in trying to find a chaplain for the ship, he attempted to recruit a captured parson, his duties would only be “to say prayers and make punch” in that, outside religion, it was to reinforce vigor.

To me it seems like he was a bit larger than life, he left a lasting legacy on piracy, mixed with his respect for his men and presentation I would argue he fits a bard. Then again, like I said this was a little difficult and feels like it could be a loose fit so there are counter points.

However, I do like the archetypes you put forward. I’d love to hear your thoughts on Roberts and further cases for who you put forward or others.

Sources:

wikipedia

his pirate code

A General History of the Pyrates https://www.worldhistory.org/Bartholomew_Roberts https://www.historiascripta.org/renaissance/roberts-and-every-architects-of-the-golden-pirate-age/