Gambler

A real gambler never gambles. He only wagers when he knows he will win. Those who make their way gambling are cheats.       

Skill Proficiencies: Deception, Insight, Sleight of Hand, P: Gambler
Tool Proficiencies: Dice or Cards 

Equipment

Fine clothes, a pair of dice and a pair of loaded dice or a deck of cards and a deck of marked cards, boot dagger, pouch with 10 gd.

Feature: Ace in the Hole 

Keep a deck of regular playing cards at hand. Once per long rest when you roll an 5 or less for an attribute, skill, saving throw or to hit roll you may add the value of the top card to the result. Face cards are 10, Aces turn the roll into a “natural 20” and Jokers are an automatic failure.
When used in combat, you lose your next turn.

Characteristics

There may be a few real gamblers who win because they are exceptionally good at playing games of chance but they are so rare they are barely worth talking about.
Your standard issue gambler is a scoundrel with a sharp wit, charming demeanor and nerves of steel. They see their opponents as “marks”, fools who exist to be parted from their coin.