Gambler

As an individual who thrives on a philosophy of high risk, high reward, you dice with death, fate and Lady Luck on a regular basis. You get your biggest thrills from living on a knife-edge, and your adrenaline surges when you win big, both in battle or at the card tables.

Level 3: Card Sharp

Your innocent face belies the cunning and honed ability of a professional player. You gain the following benefits:

Hustler: You gain proficiency in one of either Insight, Perception or Sleight of Hand, as well as 3 gaming sets of your choice. When using any of these sets, you may add double your proficiency bonus to any ability checks you make to play that specific game, as if you had Expertise.

Poker Face: Creatures have Disadvantage on Insight or Intimidation checks against you.

Sharp Card: You may use pieces from your Gaming Sets as Darts, with a maximum range of 20ft. Each gaming set contains an appropriate number of pieces that can be used this way (e.g. 52 in a standard card deck, 32 in a chess set, etc.). If the pieces are not retrieved after use, the gaming set can no longer function as such.

Level 3: Fortune's Favor

You may silently pray to Lady Luck to give yourself Advantage on one d20 Test before you roll the d20. Alternatively, you may give a creature you can see Disadvantage on one d20 Test before they roll the d20.

Either way, once you do so, you cannot do either again until you finish a Short Rest.

Level 9: Lucky Strike

You gain the following Cunning Strike options.

Gambler’s Thrust (Cost: 1d6). Roll a D6. On a roll of 1, your attack misses, regardless of the results of the attack roll or any modifiers. On a 2-5, the attack resolves as normal. On a roll of 6, you automatically score a critical hit, regardless of the results of the attack roll or any modifiers.

Hit & Run (Cost: 2d6). You may make the Disengage Action immediately as part of the current Action.

Level 13: Life on the Line

Whenever you use your Cunning Strike, instead of reducing the number of Sneak Attack dice, you may instead roll the same number of dice and deduct the total from your current Hit Points.

Additionally, if you use this ability and score a Critical Hit, you regain Hit Points equal to half the amount lost by the target, rounded up.

Level 17: Deus Ex Machina

Your exploits entertain even the Gods, and those who favour you can intervene on your behalf, often in the form of a totally unexpected twist of fate or random chance that nearly defies logic. For example, a small creature may distract a dragon long enough for you to slip past them, or a wizard's magic may backfire at just the wrong moment.

Whenever you, a creature you can see, or the Dungeon Master, would roll either an ability check or on a random table, such as an Encounter Table, Loot table, or Wild Magic table, you may use your Reaction to force them to roll twice, and you may pick the result from the rolled options.

You may use this ability once, and regain all expended uses when you finish a Long Rest.

Additionally, whenever you use Gambler's Thrust, you may roll twice and pick the result. You may only use this ability once per turn.