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An Introduction to Pirates in D&D | World Building Dungeons and Dragons 5e

Introduction to Pirates in your D&D Campaign.

How do I run Pirates in my home game?

I love pirate history and I love pirate fantasy. Both are fascinating and something I spend a lot of time thinking about. I almost started up a pirate podcast and sometimes I go spend an entire weekend dressed like a pirate. This is known among my friends, so I often get the question ‘Am I running these pirates right?’ or the request that I left them know if they do something wrong. To this, I always say ‘You’re doing great’, ‘Run them however you want’, or ‘It is your campaign’.

So here I am, going to set the record straight, on how to run pirates in your Dungeons and Dragons home game!

Pirates fighting for Treasure

Two Pirates fight for an extra share of treasure while the rest of the crew cheers them on

You are already running pirates right, you’re doing great, run them however you want, it’s your campaign. And that’s it. You are now running pirates in your game. You see, the thing about having swashbuckling rogues or fearsome buccaneers in your game is that they need to fit the way that you see them and fill the purpose of your story.

With that out of the way, we are going to get into how I would run pirates in a Dungeons and Dragons game. So let’s go ahead and get a few things out of the way. First, pirates where and still are scum, they are murderous criminals that attack ships and kill people for their own personal gain. Second, pirates are masters of their own destiny, of the open seas, and seek adventure in the furthest reaches of the world. They are both of these things. This is one of the first places we will point out the divide between fact and fiction. The fact, well even the facts about pirates, at least from The Golden Age of Piracy, are a little dicey at best. And, the fiction well, may be closer to what we consider fact. As I go through this guide I will try to inject some facts here and there so you can change the way you see pirates in your game, for me I will be referencing mostly The Golden Age of Piracy, and for the fiction side of things I am going to be focusing mostly on the Dragon Coast of the Forgotten Realms, but you can adapt much of what I have to say to any coastal, sky fairing, desert skiffing, or anything else with fantastic freebooters or the worst of scurvy black hearted dogs of the sea. Lastly, the history of The Golden Age of Pirates is amazing to read about, however, it is a very interesting time period since there is not a lot of truly reliable information about there about that small sliver of history. One of the best sources for lore on piratactical history is a book called “A General History of the Robberies and Murder of the most Notorious Pyrates” by Captain Charles Johnson, Nathaniel Mist, or Daniel Defoe, and the validity of many of the stories in here have been called to question over the years. Even the references to the many different ‘jolly rogers’ flown could have been partially, mostly, or even completely made up. And, even though there isn’t a ton of 100% solid fact, it is fun to read what historians have parted together to paint the tapestry of these masters of the sea and sail.

Okay, so how do I do pirates in my D&D game?

Anne Bonny

Anne Bonny firing her pistol

When you look at pirates they were rebelling against something and in rebelling they came up against the law and merchants; who happened to pretty much be the law as well as merchants. Some pirates where sailors with the royal navy and after their ships got captured they joined the pirate crew through the lure or riches. Or, there is always the privateers who are not part of the right country, so they are considered pirates too. What are your pirates? What Drives them? These are questions that borrowing a little from history will help you find the motivations begins their actions

Very little of the Pirate history tells of stories of people striking out for adventure, there was always something that drove them to fly under the black flag. From poverty to oppression, to being in the wrong place at the wrong time drove these men and women to the sea.

During the golden age there were stories of men being drafted into the navy and paid half of this pay up front and the second have when they returned to port. However, the issue was that these men would be at sea for six months or more at a time and not be able to get enough money to their loved ones to be able to survive. These men often signed up with the first pirate crew that would take them, it allowed them to send money back to those who were most important to them. A pirate like this might be a bit more forgiving when capturing a ship, but his top concerns are supporting his family, not getting caught, and making it home alive.

Handsome Pirate

This handsome pirate is ready to ship out with his new rifle.

History tells us the stories of Anne Bonny and Mary Read; Anne running away from her family looking for acceptance and Read who had a career in the military posing as a man until her ship was caught and she signed up with “Calico Jack” Rackham. While on that ship Anne Bonny and Mary Read where thought to be lovers. This is speculation, but looking at both of these women you can see people who were driven by trying to escape aspects of society that were keeping them chained down. Neither of these women wanted to stay home and be wed off to whomever their fathers wanted them to marry. A pirate like either of these women could be running away from the regime of society. They don’t want to conform to society and they are willing to die trying to prevent that.

Mary Read with Axe and Sword

Mary Read with Axe and Sword

There are two different types of mugs and the stories of these two particular type each have a story back to piracy. These mugs are those with a clear bottom and those with a lid. Now, I know that these are just myths and I am sure the fact is much more reasonable as to why these kinds of mugs exist, but it is more fun to think of pirates as the reason. The story goes, you are drinking in an inn and as you take your last drag of ale you find a shiny coin in the bottom of your mug. Congrats you have just accepted payment of the king to be conscripted into his royal highness’s navy. You will start in the morning, don’t be late or that is treason. So they put the glass on the bottom so you could see if a coin was in your drink or maybe that is why they put the lid on it, so when you weren’t paying attention someone couldn’t slip a coin in. These sailors would jump crew at the first chance they got. These are fun ways to getting characters onto a boat, or meeting sympathetic NPCs. Pirates like this are more likely to be kind to those they capture offering them the same kindness they got from the pirates before them, they might also be so disenfranchised they will just gut your captain and throw you to the sharks.

Then there are the tales of powerful villains of the sea like Black Beard and Black Bart. These fearsome pirate captains had crews of well-trained sailors who would follow their captains into battle and not worry about the consequences. These facts may not be completely true, however they were still criminals and guilty of many crimes. But, having these types of pirate captains who are out for blood and a hungry crew that follows their every order, are a fantastic way of having a villain who will do anything to get what they want. They won’t back down from a fight, they will enslave, and they will kill in the most brutal way possible. There are very few groups that are more fearsome and more fun for a table full of players to encounter.

Captain Blackbeard

A brace of pistols was one of the many ways Blackbeard struck fear into the hearts of his captives

The last kind of pirate we are going to outline are the ones that just happen to be flying the wrong flag at the time. During the golden age of piracy there was something a king or queen could give a private ship called a writ. The writ was a contract from a King or Queen that you could go out and sack enemy ships taking most if not all of the cargo for yourself and your crew. You would return a hero. And, while you are out being a hero to your country you would be a pirate to the enemy. And even so, sometimes you would return home and not get the hero’s welcome. Captain William Kidd was a privateer for the Queen’s navy and while he was out sinking ships and taking his share with the writ from the Queen she then shifted alliances and he was then taking allied ships not knowing, and returning home a villain. Now, there is much more to that story, including the myth about buried treasure. But, these are great pirates when you have different rulers. They may give you no quarter, they may be heavily armed and ready to kill. I often find these pirates interesting in larger scale campaigns.

When you want pirates in your campaign it always adds more depth to them when you have the motivation of your sailors. And, I feel like with that kind of information you can easily build an entire campaign around them. Once you know why is pirate is doing what they do, the easier it will be for you to answer the question “Am I running these pirates correctly?”

What’s Next?

Pirates are great enemies, fantastic heroes, and amazing NPCs to put into your home D&D game. It is also a great jumping off point, chapter, or even the entire campaign worth of stories. Over the next few months, I plan to outline more details on how to use pirates in Dungeons and Dragons, Forgotten Realms, or any RPG out there. I hope you find great ways to introduce these colorful and interesting characters into your game, and maybe learn a little along the way. So please check back soon when we move to our next chapter on Pirates.

Do you have any opinions, things you would like to see a write-up on, or fun ways you present pirates? Feel free to let me know

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