Pirate Raider

You spent your youth under the sway of a dread pirate, a ruthless cutthroat who taught you how to survive the high seas. You've indulged in larceny and sent more than one deserving soul to a briny grave. Fear and bloodshed are no strangers to you, and you've garnered a somewhat unsavory reputation in many a port town.

For a similar background, see my Pirate Captain homebrew.

Skill Proficiencies: Intimidation, Deception

Tool Proficiencies:

• navigator's tools and sky/sea vehicles
• (a) cook's tools, (b) disguise kit, (c) forgery kit, (d) poisoner's tools, (e) thieves' kit, or (f) gaming set

Languages: Common and Thieves' Cant

Equipment:

• (a) disguise kit, (b) forgery kit, (c) thieves tools, (d) poisoner's tools
• (a) hand crossbow or (b) shortbow
• (a) hidden dagger or (b) palm pistol
• rope (50 ft), money pouch (10 gp), gaming set, flask, lucky charm, and pirate hat
• crew-specific equipment

Crew-Specific Equipment

1. First Mate: studded leather armor, rapier, blunderbuss, navigator's tools, spyglass
2. Crow's Nest: leather armor, dart gun, spyglass, torch, signal whistle, 10-ft ladder, compass
3. Ship Cook: leather armor, simple melee weapon, cook's utensils, poison vial, compass
4. Quartermaster: studded leather armor, shotgun, whip, navigator's tools, hooded lantern, rations/supplies
5. Gunner: leather armor, pistol, musket, simple melee weapon, gunpowder horn, compass
6. Powder Monkey: leather armor, grenade launcher, simple melee weapon, bombs (3), dynamite (3), blasting powder, compass
7. Navigator: leather armor, rapier, navigator's tools, cartographer's tools, spyglass, maps/scrolls
8. Surgeon: leather armor, healing kit, compass

Suggested Characteristics

Optional: Choose one or two from each category or make up your own.

d8	Personality Trait
1	You always work hard at sea and play hard on land.
2	You have a way of getting people to do what you want them to by making them think it’s their idea.
3	You are uneasy on land and prefer to be aboard a ship whenever possible.
4	You are a prolific gambler, always willing to take a risk on a game of chance.
5	Most people find your speech very difficult to understand, but that doesn't stop you from talking.
6	You are very direct and usually speak your mind without worrying about the feelings of other people.
7	You are always willing to switch allegiances if doing so will help you get what you want.
8	To you, a tavern brawl is a nice way to get to know a new city.

d6	Ideal
1	Superiority. Anything worth doing is worth doing better.
2	Opportunism. Life is not just a matter of having good cards, but of playing a poor hand well.
3	Ambition. Everyone wants things, I am just better than most at getting them.
4	Dominance. Aboard my ship, anyone who doesn't follow my orders is welcome to walk back to dry land.
5	Autonomy. My life means nothing if I can’t live it on my own terms.
6	Coercion. It is better to be feared than to be respected.

d6	Bond
1	A rival pirate has a vendetta against you for your role in some past misadventure.
2	Your life of piracy on the seas has separated you from your true love and you long to be reunited.
3	The ship you served aboard or the crew that you served with has gotten you out of danger on too many occasions to count and are now the most important thing to you.
4	There was once a great treasure within your reach but you lost it and now seek nothing more than to reclaim it.
5	The dread pirate that taught you was once the victim of a mutiny and you will not rest until every mutineer has paid for their disloyalty.
6	You are being relentlessly pursued by a naval officer dead-set on bringing you to justice.

d6	Flaw
1	You revel in your infamy and can’t resist the urge tell everyone you encounter who you are and what you're capable of.
2	You bristle under authority and rarely follow orders without challenging them.
3	You are overconfident in your plans, especially when the odds are stacked against you.
4	You never tell the truth when a lie will suffice.
5	Although you feign apathy, your conscience is a constant companion.
6	You are impulsive and often make important decisions without first gauging the options.

Contacts

Optional: Choose an ally and an antagonist.

d4	Contact
1	Shady merchant who doesn't ask questions
2	Cartographer, archeologist, or treasure hunter
3	Oracle who owes you a favor
4	Dirty official you blackmailed into helping you

d4	Non-contact
1	Ship officer with a vendetta
2	Captain you mutineered against
3	Vengeful pirate victim
4	Sea creature with a grudge