Mafia Boss

You were raised by a mafia boss to be their successor. You know all about street life, and it's familiar to you. You're a hardened criminal, and you have been for all your life.

Skill Proficiencies: Choose two. Sleight of Hand, Perception, Deception, Intimidation, Stealth, and Persuasion. 

Tool Proficiencies: Choose one. Thieves’ tools, forgery kit, and disguise kit.

Languages: Choose one. Deep Speech, Primordial, Infernal, Orc, and Abyssal.

Equipment: Pepperbox and 20 pepperbox ammunition or 25gp 

Suggested Characteristics

I've killed many men, and I'm not afraid to kill more.

I'll lay down my life for my companions.

If my companion betrays me, they'll face a worse fate than my enemy.

 

d5	Personality Trait
1	I always have a plan for what to do when things go wrong.
2	The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden.
3	I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
4	I blow up at the slightest insult.
5	If you help me, I'll always return the favor, no matter what it may be.

d3	Ideal
1	Allies. My allies are the only things that matter to me. (Lawful)
2	Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3	Greed. I will do whatever it takes to become wealthy. (Evil)

d3	Bond
1	I’m trying to pay off an old debt I owe to a generous benefactor.
2	Someone I loved died because of a mistake I made. That will never happen again.
3	My ill-gotten gains go to support my family.

d4	Flaw
1	An innocent person is in prison for a crime that I committed. I’m okay with that.
2	If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
3	When faced with a choice between money and my friends, I usually choose the money.
4	When I see something valuable, I can’t think about anything but how to steal it.