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.
- Skill Proficiencies: Intimidation, your choice of one between Sleight of Hand or Stealth
- Tool Proficiencies: Your choice of one from Thieves’ Tools, Forgery Kit, or Disguise Kit.
- Languages: your choice of one
- Equipment: A set of dark common clothes including a hood, a set of tools to match your choice of tool proficiency, and a pouch containing 15 gp
There are many kinds of criminals, and within a thieves’ guild or similar criminal organization, individual members have particular specialties. Even criminals who operate outside of such organizations have strong preferences for certain kinds of crimes over others. Choose the role you played in your criminal life, or roll on the table below.
| d8 | Criminal Specialty |
|---|---|
| 1 | Blackmailer |
| 2 | Burglar |
| 3 | Enforcer |
| 4 | Fence |
| 5 | Highway robber |
| 6 | Hired killer |
| 7 | Pickpocket |
| 8 | Smuggler |
You have gained enough clout within your organization that you can call in a favor from your contacts, should you be close enough to a center of your organization's activity. A request for a favor can be no longer than 20 words and is passed up the chain to an undisclosed officer for approval. This favor can take a shape up to the DM’s discretion depending on the request, with varying speeds of fulfillment: If muscle is requested, an NPC minion of your organization can temporarily aid the party. If money is needed, a small loan can be provided. If you’ve been imprisoned, they can look into breaking you free, or paying off the jailer.
The turn comes when a favor is asked to be repaid. The favor debt can be called in without warning, and many times with intended immediacy. Perhaps the player is called to commit a specific burglary without the option to decline. Maybe they must press a dignitary for a specific secret at an upcoming ball. your organization could even request a hit on an NPC, no questions asked or answered. The DM is to provide a debt call proportionate to the favor fulfilled. If a favor is not repaid within a reasonable period of time, membership to your organization can be revoked, and if the debt is large enough, the player may become the next hit contract to make the rounds
Suggested Characteristics
Criminals 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 thieves, but criminals 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. 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. |
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