You are an experienced pirate with a history of breaking the law. You have spent a lot of time among other pirates and still have contacts within the criminal underworld. You’re far closer than most people to the world of murder, theft, and violence that pervades the underbelly of civilization, and you have survived up to this point by flouting the rules and regulations of society.
- Skill Proficiencies: Deception, Intimidation
- Tool Proficiencies: Water vehicles, Navigator's tools
- Languages: You know the thieves cant, and one other language of your choice.
- Equipment: A flask, a [Tooltip Not Found], a rapier, and a pouch containing 15 gp
There are many kinds of pirates, and within a crew , individual members have particular specialties. Even pirates who operate outside of such organizations have strong preferences for certain roles over others. Choose the role you played in your criminal life, or roll on the table below.
| d8 | Position |
|---|---|
| 1 | Captain |
| 2 | First Mate |
| 3 | Boarding Party |
| 4 | Firearms/Explosives expert |
| 5 | Cook |
| 6 | Slave |
| 7 | Ambassador |
| 8 | Common Crewmember |
You have a reliable and trustworthy crew who you can call upon when needed. They can deliver messages and contraband or assist in battle
Suggested Characteristics
Pirates might seem like villains on the surface, and many of them are villainous to the core. But some have an abundance of endearing, if not redeeming, characteristics. There might be honor among pirates, but they rarely show any respect for law or authority.
| d8 | Personality Trait |
|---|---|
| 1 | I always have a plan for what to do when things go wrong. |
| 2 | I am always calm, no matter what the situation. I never raise my voice or let my emotions control me. |
| 3 | The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden. |
| 4 | I would rather make a new friend than a new enemy. |
| 5 | I am incredibly slow to trust. Those who seem the fairest often have the most to hide. |
| 6 | I don’t pay attention to the risks in a situation. Never tell me the odds. |
| 7 | The best way to get me to do something is to tell me I can’t do it. |
| 8 | I blow up at the slightest insult. |
| d6 | Ideal |
|---|---|
| 1 | Honor. I don’t steal from others in the trade. (Lawful) |
| 2 | Freedom. A ship and a good crew is freedom from the chains of land. (Chaotic) |
| 3 | Charity. I steal from the wealthy so that I can help people in need. (Good) |
| 4 | Greed. I will do whatever it takes to become wealthy. (Evil) |
| 5 | People. I’m loyal to my crew, not to any ideals, and everyone else can take a trip down to Davy Jones' locker for all I care. (Neutral) |
| 6 | Redemption. There’s a spark of good in everyone. (Good) |
| d6 | Bond |
|---|---|
| 1 | I’m trying to pay off an old debt I owe to a generous captain. |
| 2 | My ill-gotten gains go to support my family. |
| 3 | Something important was taken from me, and I aim to steal it back. |
| 4 | I will become the greatest pirate that ever lived. |
| 5 | I’m guilty of a terrible crime. I hope I can redeem myself for it. |
| 6 | Someone I loved died because of a mistake I made. That will never happen again. |
| d6 | Flaw |
|---|---|
| 1 | When I see something valuable, I can’t think about anything but how to steal it. |
| 2 | When faced with a choice between money and my crew, I usually choose the money. |
| 3 | If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it. |
| 4 | I have a “tell” that reveals when I’m lying. |
| 5 | I turn tail and run when things look bad. |
| 6 | An innocent person is in prison for a crime that I committed. I’m okay with that. |
Although your capabilities are not much different from those of pirate, you learned and practiced them in a very different context: as a privateer. You might have been an officially sanctioned agent of the crown, or perhaps you sold your bounties to the highest bidder.
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