Gangster Dropout

As a kid, you joined a gang. It was all fun and games at first, until the first time they asked you to commit your first truly evil act. You refused, and they mocked you for it. They said it was because you were a coward, but you knew better: it was because you knew it was wrong. Nevertheless, you began to fall lower and lower in the gang's hierarchy.

The final straw was when they undid a particular act of your kindness. Perhaps you saved a small cat from drowning, then they chucked it right back into the river the next day. Maybe you helped an old grandma cross the road, and they drove a horse into her right after. Whatever the case, you were done with the gang. You walked, and you didn't care whether the gang liked it or not.

But here comes the problem: You're not smart. You're not good at magic. You're not even that good-looking. What are you good at? Well, your fists, you suppose. With nothing but your brawn, you set out to make your own way in the world, and prove to yourself that only you can shape the person you're going to be.

Skill Proficiencies: Intimidation, Medicine (more for role-playing purposes) or Acrobatics (more for practical purposes)

Tool Proficiencies: One type of gaming set, thieves’ tools

Languages: Common, Thieves' Cant

Equipment: A crowbar, a set of dark common clothes including a hood, and a pouch containing 15 gp

Suggested Characteristics

As a far more humble take on the villain archetype, your character is rather conflicted. From your time spent in the gang, you picked up ways of acting belligerent and pushing people around to get what you want, but underneath, you have a far less villainous heart. You don't have to be Good, but you're definitely not Evil. You might act like a hoodlum, but you refuse to perform any acts that will bring true harm to anyone.

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. Chains are meant to be broken, as are those who would forge them. (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 friends, 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 thief 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	An innocent person is in prison for a crime that I committed. I’m okay with that.