Gambler

 You’ve spent countless nights gambling your life away in taverns, ships, and back alleys. Whether by skill or luck, you’ve developed a knack for games of chance and turning situations to your favor.

• Luck of the Draw:
  When you make an ability check or saving throw and dislike the outcome, you can reroll the die and use the new result. Once you use this feature, you can’t use it again until you finish a long rest.

• Games of Chance Expertise:
  You gain expertise in a gaming set of your choice (such as dice, cards, or dragonchess). This means you double your proficiency bonus for any ability check you make with the chosen gaming set.

• Risky Wager:
  When you make a Charisma (Deception), Charisma (Persuasion), or Wisdom (Insight) check involving a gamble or bet, you can choose to roll an additional d4 and add it to the result. You can use this feature a number of times equal to your Charisma modifier (minimum of once), regaining all uses after a long rest.

Cheat

You’ve perfected the art of tampering with gaming tools to sway the odds in your favor, turning any gamble into an opportunity for profit.

• Tampered Tool:
  Choose one gaming tool you are proficient with (such as playing cards, dice, or dragonchess pieces). Over the course of a short rest, you can tamper with the tool to rig it in subtle ways, granting it the following properties:

  • Advantage in Play: When using the tampered tool during a game or contest, you have advantage on Dexterity (Sleight of Hand) checks and Charisma (Deception) checks made to influence the outcome.

  • Hidden Modifications: The tampered tool is difficult to detect. A creature inspecting the tool must succeed on a Wisdom (Perception) or Intelligence (Investigation) check (DC = 8 + your proficiency bonus + your Dexterity modifier) to notice the tampering.

• Cheat in Action:
  As an action, you can subtly manipulate the game in your favor while using your tampered tool. Make a Dexterity (Sleight of Hand) check contested by an opponent’s Wisdom ([skill]Perception) check. On a success, you rig the game to guarantee a favorable outcome, such as ensuring a specific card is dealt or dice roll lands as intended.