Your family has a history of crime, and you lost one or more members this way. Seemingly from birth, you've always had a penchant for stealing shiny objects, food, whatever might strike your fancy. Knowing a second language has always been helpful, allowing you to understand the gray areas of communication even better than your peers. You have always had a way with people, talking your way out of rope since you could speak. You know what makes them tick, you can tease out their hearts’ desires after a few minutes of conversation, and with a few leading questions you can read them like they were children’s books. It’s a useful talent, and one that you’re perfectly willing to use for your advantage.

Perhaps you previously retired from a life of crime, have been working to kick the habit, or were forced back into it by circumstance. It seems no matter what you do, you always end back up here. Mostly, you don't think on it too much-- everyone has to get by, right? And besides, the only way you fit in is by going against the status quo. You were born a swindler, and will die a swindler.

Skill Proficiencies: Deception, Perception

Tool Proficiencies: Disguise kit, Forgery kit

Equipment: A set of fine clothes, a disguise kit, tools of the con of your choice (ten stoppered bottles filled with colored liquid, a set of weighted dice, a deck of marked cards, or a signet ring of an imaginary duke), and a pouch containing 15 gp

Suggested Characteristics

Swindlers are colorful characters who conceal their true selves behind the masks they construct. They reflect what people want to see, what they want to believe, and how they see the world. But their true selves are sometimes plagued by an uneasy conscience, an old enemy, or deep-seated trust issues.

d8	Personality Trait
1	I fall in and out of love easily, and am always pursuing someone.
2	I have a joke for every occasion, especially occasions where humor is inappropriate.
3	Flattery is my preferred trick for getting what I want.
4	I’m a born gambler who can’t resist taking a risk for a potential payoff.
5	I lie about almost everything, even when there’s no good reason to.
6	Sarcasm and insults are my weapons of choice.
7	I keep multiple holy symbols on me and invoke whatever deity might come in useful at any given moment.
8	I pocket anything I see that might have some value.

d6	Ideal
1	Independence. I am a free spirit—no one tells me what to do. (Chaotic)
2	Fairness. I never target people who can’t afford to lose a few coins. (Lawful)
3	Charity. I distribute the money I acquire to the people who really need it. (Good)
4	Creativity. I never run the same con twice. (Chaotic)
5	Friendship. Material goods come and go. Bonds of friendship last forever. (Good)
6	Aspiration. I’m determined to make something of myself. (Any)

d6	Bond
1	I fleeced the wrong person and must work to ensure that this individual never crosses paths with me or those I care about.
2	I owe everything to my mentor—a horrible person who’s probably rotting in jail somewhere.
3	Somewhere out there, I have a child who doesn’t know me. I’m making the world better for him or her.
4	I come from a noble family, and one day I’ll reclaim my lands and title from those who stole them from me.
5	A powerful person killed someone I love. Some day soon, I’ll have my revenge.
6	I swindled and ruined a person who didn’t deserve it. I seek to atone for my misdeeds but might never be able to forgive myself.

d6	Flaw
1	I can’t resist a pretty face.
2	I’m always in debt. I spend my ill-gotten gains on decadent luxuries faster than I bring them in...
3	I’m convinced that no one could ever fool me the way I fool others.
4	I’m too greedy for my own good. I can’t resist taking a risk if there’s money involved.
5	I can’t resist swindling people who are more powerful than me.
6	I hate to admit it and will hate myself for it, but I’ll run and preserve my own hide if the going gets tough.