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You make your living through games of chance. Being lucky helps. Being able to cheat helps even more.

 
Skill Proficiencies: Skill Proficiencies: Sleight of Hand, Insight, Deception
Tool Proficiencies: Tool Proficiencies: Three Types of Gaming Set
Equipment:
A deck of cards, a deck of marked cards, a set of dice, a set of loaded dice, and a pouch containing 15 gp.

 

 
Deceptive Specialty

Most con artists have a specialty, a specific way to do business or a certain set of items they can always sell to someone, no matter the circumstances.

d7 Deceptive Specialty
1 You sell items that you steal from other people, usually claiming they are magical.
2 You say you will save others from their sins. With a fee of course.
3 You bet on rigged games, or you rig the games yourself.
4 You sell people 'potions' which are really just bottles of colored water.
5 You perform magic tricks as a show. But it is all slight of hand and a great way to distract people.
6 You sell stolen weapons, claiming that they had a long and valiant backstory.
7 You trick honorable adventurers to sign a pact with you that guaranties protection or riches.
 
Feature: Cheater

You know how to cheat at games of chance.  When playing such games, you can make a sleight of hand check with advantage to substitute in marked cards, loaded dice, or any other appropriate manner of cheating.  The other players contest your sleight of hand check with a perception check.  If any other player succeeds in their perception check, you are caught, and consequences will follow (violence, calls for the sheriff, etc.). If you are not caught, you win the game.

 
Suggested Characteristics

Your persuasive charm and experience in deceiving others have led you towards a more chaotic and fun-loving personality.

d5 Personality Trait
1 I like seeing how far I can go with people before striking a nerve, and I’ll purposely lie, make things up, or avoid speaking the truth to see what happens.
2 I never really plan anything out, I go with the flow and see what I want to do in the current moment.
3 I think anyone who’s nice to me is hiding evil intent.
4 I don’t like to bathe.
5 I like to sleep by myself, it's much safer and more comfortable.
d5 Ideal
1 Respect. All people, rich or poor, deserve respect. (Good)
2 Aspiration. I’m going to prove that I’m worthy of a better life.
3 Community. We have to take care of each other, because no one else is going to do it. (Lawful)
4 Retribution. The rich need to be shown what life and death are like in the gutters. (Evil)
5 Change. The low are lifted up, and the high and mighty are brought down. Change is the nature of things. (Chaotic)
d5 Bond
1 I sponsor an orphanage to keep others from enduring what I was forced to endure.
2 I owe my survival to another urchin who taught me to live on the streets.
3 I escaped my life of poverty by robbing an important person, and I’m wanted for it.
4 I scammed the wrong person and I’m currently on the run, trying to find something that can help fix this situation.
5 I need to collect money for a dream that I have.
d5 Flaw
1 If I’m outnumbered, I will run away from a fight.
2 I’d rather kill someone in their sleep than fight fair.
3 It’s not stealing if I need it more than someone else.
4 The truth can be painful to deal with, so I lie in attempts to smooth everything over easily.
5 Sometimes things that are shiny are hard to resist.
 
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