Gambler

The world is filled with a colorful palette of gamblers, swindlers and other scoundrels. While gambling is considered a respectable profession, few play by the rules and even fewer are willing to accept defeat. Hence the first rule to gambling is to always play with your back to the wall. Otherwise you'll never see the dagger coming your way. And you will see daggers come your direction. After all you are always winning and that means someone else is losing...

Placing Bets

Starting at 3rd level, your profession lets you take dangerous risks with high rewards. Whenever a creature you can see (including yourself) makes an Ability Check, Saving Throw or Attack roll you can bet on the outcome of that roll. If the creature is making an Ability Check, you bet if the roll (excluding modifiers) will be higher or lower/equal to 10. If the creature is making an Attack roll or Saving Throw, you bet if the creature will succeed or fail.

If you guess correctly, you get advantage on the next roll of that type you make. If you're wrong, nothing happens.

You can use this feature a number of times equal to your proficiency bonus per short rest.

Loaded Dice

At 3rd level, you have become very proficient wit your set of loaded dice. If you roll a 1-7 on Charisma (Performance and Deception) and Dexterity (Sleight of Hand) Checks you can choose to treat that roll as an 8.

Ace In The Hole

At 9th level you have made sure that you always have one last trick up your sleeve. During your turn you can choose to take one additional Action.

Once you've used this feature you cannot use it again until you have finished a short rest.

Poker Face

At 13th level you get advantage on all Charisma (Deception) and Wisdom (Insight) checks you make.

All-In

At 17th level you can place the outcome of a situation on a surprisingly high risk, high reward gambit. When rolling a d20 you can choose to instead flip a coin. You decide which side of the coin stands for a natural 1 and which side of the coin stands for a natural 20.

If you succeed in "rolling" a natural 20 that way, you can't use this feature until you have finished a Short Rest.