Gambler / High Roller

You are an experienced gambler with a history of winning - and losing - big. You have spent a lot of time among other gamblers and the criminal underworld. You’re far closer than most people to the world of book-making, theft, severed fingers, and broken knees that pervades the underbelly of civilization, and you have survived up to this point by knowing when to fold and whose bluffs not to call.

Notes:  This background's feature requires a coin with two unique faces that can be designated as heads and tails. Advantage on a coin toss means to flip two coins and take a heads if at least one coin is heads. Disadvantage on a coin toss means to flip two coins and take a tails if at least one coin is tails.

 

Skill Proficiencies: Deception or Persuasion and either Sleight of Hand, Perception, or Insight

Tool Proficiencies: Any two gaming sets

Equipment: A gaming set, a lucky coin, a set of common clothes with a hood or a set of fine clothes, and a pouch containing 20 gp

Suggested Characteristics

Gamblers might seem like lost souls or boisterous scoundrels on the surface, and many of them are lost in the depths of an addiction. But some have an abundance of endearing, if not redeeming, characteristics: boldness, cunning, insight, courage.

Many gamblers are superstitious and believe their personal rituals have the ability to influence chance.

d8	Personality Trait
1	I always know when to stay and when to fold.
2	I can bluff my way out of any situation.
3	I've been known to deal from the bottom of the deck.
4	I like to make friendly wagers during arugments.
5	I don't trust anyone who doesn't believe in luck.
6	I don’t pay attention to the risks in a situation. Luck is on my side.
7	The best way to get me to do something is to tell me the odds are against me.
8	I fall into a depression when my luck runs out.

d6	Ideal
1	Honor. I don’t cheat. (Lawful)
2	Freedom. Let the chips fall where they may. (Chaotic)
3	Charity. If I cheat it's only so that I can help people in need. (Good)
4	Greed. I will do whatever it takes to win. (Evil)
5	People. My wagers are only ever friendly ones. (Neutral)
6	Redemption. Chance smiles upon us for changing out ways. (Good)

d6	Bond
1	I’m trying to pay off an old debt I owe to a dangerous bookie.
2	My winnings are all that supports my family.
3	I bet something important to me and lost to a cheat; I must get it back.
4	I've wagered my life and lost; now I'm on the run.
5	I'm welcome as a high-roller in most gambling dens.
6	I lost my friends and family after gambling away my savings.

d6	Flaw
1	I must perform specific rituals to keep up my luck.
2	When faced with a choice between doing the right thing and earning some coin, I usually choose the coin.
3	I can't turn down a wager.
4	I have a “tell” that reveals when I’m bluffing.
5	I fold at the first sign of trouble.
6	My lying and cheating has lost other people their hands and, in some cases, their heads. I’m okay with that.