Gambit

Winning isn’t everything, it’s just the only thing that matters. Because who the hell plays to lose, especially with everything you put on line? That’s why you have a little bit of luck magic on your side to tip the scales in your favor. Because of course, what kind of rogue would you be if you couldn’t bend your odds to your favor.

At the end of the day, it's fun to test your luck! Some may reprimand you for treating life as a game but why shouldn’t you? In your case, you have the ability to turn anything into a fun opportunity to test for chance. Chess, playing cards, maybe even your life you’ll gamble with. Anyone who adventures is testing their odds of survival, you’re just doing it with style and finesse.

Chess Master

3rd-level Gambit feature

Game Proficiency. You gain proficiency with Dragonchess.

Roll Play. At the start of your turns, you can choose to reduce your next Sneak Attack damage roll by 1d6. You can then roll the d6 on the Chess table and select a target of your choice within 60 feet of you. The target gains the effects of the result you rolled. You can use this feature a number of times to equal your Dexterity modifier. You regain all expended uses on a Short or Long rest.

(If the effect requires a saving throw, the DC equals 8 plus your Dexterity modifier and Proficiency Bonus.)

Chess

Damage Die (1d6)	Chess Piece Result
1	Queen. The target’s speed increases by 10 feet, ignores Difficult Terrain, and cannot provoke Opportunity Attacks until the end of its next turn.
2	King. The target must succeed on a Dexterity saving throw. At the end of your current turn, the next attack roll against the target is a Critical hit.
3	Bishop. The target becomes Invisible while the next damage roll it against it has a bonus equal to your Rogue level until the end of its next turn.
4	Rook. The target gains Temporary Hit Points equal to your Rogue level but its Speed is reduced by 10 feet until it has no Temporary Hit Points.
5	Knight. The target gains a Flying speed equal to its Speed until the end of its next turn, floating gently to the ground if it is still aloft.
6	Pawn. The target must succeed on a Wisdom saving throw or be Charmed by you until the end of its next turn.

Upper Hand

9th-level Gambit feature

Game Proficiency. You gain proficiency with Playing Cards.

Card Tricks. You have magically enhanced a deck of cards into lethal weapons. Your playing cards count as a Simple Ranged weapon with which you are proficient. It has the Finesse, Light, and Thrown properties (Range 20/60). You can use the Attack action or a Bonus action to make an attack with these cards. You automatically hit the target if it is an ally. Choose one of the following options or roll 1d4 to determine the effect.

Clubs (1). The target is pushed up to 15 feet away from you.

Diamonds (2). The target gains a +2 bonus to AC until the end of your next turn.

Hearts (3). The target regains Hit Points equal to 1d4 + your Dexterity modifier.

Spades (4). The target takes Force damage equal to 1d4 + your Dexterity modifier.

Lucky Bastard

13th-level Gambit feature

You can’t be a skilled game master without a little luck on your shoulder. Whenever you roll a 1 or a 20 on a D20 test, you gain Heroic Inspiration. In addition, you can have a number of uses of Heroic Inspiration equal to your Dexterity modifier. You lose all accumulated uses when you finish a Long Rest.

Ultimate Gamble

17th-level Gambit feature

You’re going to make an incredible gamble that can either be disastrous or extremely favorable. When you are below 100 Hit Points, once per Long rest as a Magic action, you can roll 1d100. If you roll equal to or higher your current Hit Points you cast Foresight on yourself. If you roll below your current Hit Points, you cast Power Word Kill targeting yourself.