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You are an experienced criminal with a history of breaking the law. You have spent a lot of time among other criminals 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. Your family is everything, and so is its loyalty. If either is threatened you have to take care of it, for the family.

 
Skill Proficiencies: Deception, Stealth, Survival
Tool Proficiencies:  Thieves’ Tools
Languages: Thieves Cant
Equipment: A crowbar, a set of dark common clothes including a hood, a pouch containing 20 gp, and a Disguise Kit
 
"I know a guy."

As the head of a powerful family you have a reliable and trustworthy network of contacts who act as your liaisons and goons. You know how to get messages to and from your contact, even over great distances; specifically, you know the local messengers, corrupt caravan masters, and seedy sailors who can deliver messages for you, or whatever you need from the table below.

d7 "I know a guy."
1 Right-hand-man
2 Enforcer
3 Fence
4 Family Doctor
5 Cleaner
6 Goon
7 Smuggler
 
Feature: Heartless

Sometimes, you need to teach someone a lesson. You may need to encourage someone to get a job done. Maybe you need to put the squeeze on some schmuck who doesn't know his place Twice per short rest you can add a D4 to any charisma roll

 
Suggested Characteristics
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 disrespect.
d6 Ideal
1 Honor. I don’t steal from others in the trade. (Lawful)
2 Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3 Charity. I do my best in the community to help the community. (Good)
4 Greed. I will do whatever it takes to become wealthy. (Evil)
5 Family. I’m loyal to my family, not to any ideals, and everyone else can take a trip down the Styx 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 benefactor.
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 boss 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 friends, 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 It took a mountain of bodies to get where I am, and I’m okay with that.
 
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