Gambler

As a gambler, you master the skill of betting high and winning big, and often losing just as big. You must be able to stop when you lose your bet, but when you do hit the jackpot, the results can be spectacular.

High Stakes

Starting at 3rd level, you learn to rely on your luck when the odds aren't in your favor, and how to raise the stakes for bigger wins. You can benefit from Sneak Attack if the attack had disadvantage, and when you make an attack without disadvantage, you can cause it to be rolled with disadvantage (even if it originally had advantage, and this disadvantage cannot be negated in any way), and if you do, you gain an extra d6 of Sneak Attack damage, or 3d6 if it originally had advantage.

Additionally, you gain proficiency in the Performance and Persuasion skills.

Roll the Slots!

Starting at 9th level, you gain the following Cunning Strike option:

Roll the Slots (cost: 3d6). Roll 3d6. If each die rolls a different number, apply the effects of the "loss" effect of one of the numbers rolled (your choice). If exactly two dice roll the same number, apply the effects of the "win" effect of that number. If all three dice roll the same number, apply the effects of the "jackpot' effect of that number. Note that "the target" refers to the creature hit by the attack unless otherwise specified, and if an effect calls for a saving throw, the DC equals 8 + your proficiency bonus + your Charisma modifier.

Slot Effects:

1. Loss: the attack deals an extra 2d4 fire damage. Win: the attack deals an additional 8d8 fire damage. Jackpot: the attack deals an additional 14d12 fire damage, and the attack releases a massive explosion, forcing each creature of your choice within 30 feet of the target (excluding itself) to make a Dexterity saving throw or take the same damage.
2. Loss: the target must subtract 1d6 from the next saving throw it makes. Win: the target must succeed on a Wisdom saving throw or be cursed for one minute, suffering the effect of a loss on a success. While cursed in this way, it must subtract 1d4 from all d20 tests it makes. Jackpot: the target must succeed on a Wisdom saving throw or be cursed for 1 minute or suffering the curse of a Win on a success (as though it had failed its saving throw). While cursed in this way, it must subtract 1d12 from all d20 tests it makes, and it takes necrotic damage equal to the amount subtracted whenever this happens.
3. Loss: the target takes an extra 1d4 cold damage and its speed is halved until the start of your next turn. Win: the target must succeed on a Constitution saving throw or take 2d8 cold damage and be restrained by ice for 1 minute or until it or a creature within 5 feet of it uses an action to make a Strength (Athletics) check (DC is equal to the save DC) to break the ice. On a successful save, it takes half as much damage, and its speed is reduced to 0 until the start of your next turn. Jackpot: the target must succeed on a Constitution saving throw. On a failure, it takes 4d10 cold damage and is turned into a frozen statue for 1 hour, being petrified for that time but being vulnerable to fire and bludgeoning damage instead of resistant to them. On a success, they take half as much damage and are restrained as though they had failed a save against the Win effect.
4. Loss: you gain 2d12 temporary hit points. Win: you and a creature of your choice within 30 feet of you regain 4d12 hit points. Jackpot: you and each creature of your choice within 60 feet of you regain 8d12 hit points and gain the benefits of the greater restoration spell.
5. Loss: the target takes an extra 1d6 poison damage and must succeed on a Constitution saving throw or be poisoned until the start of your next turn. Win: the target takes 3d6 poison damage and is poisoned until the start of your next turn. It also must succeed on a Constitution saving throw or be paralyzed while poisoned in this way. Jackpot: the target takes 10d6 poison damage and is poisoned for 1 minute. It also must succeed on a Constitution saving throw or take an additional 10d6 poison damage and be paralyzed while poisoned in this way.
6. Loss: You may make an additional attack with the same weapon against the target with no further action cost. Win: you may make up to two additional attacks with the same weapon against the target with no further action cost. These attacks have advantage and you can apply Sneak Attack on one of them. Jackpot: you may make up to four additional attacks with the same weapon against the target and an additional one against up to four creatures within the weapon's reach/range. These attacks have advantage, can apply Sneak Attack, and any hit with them counts as a critical hit. Note that Roll the Slots cannot be used with attacks given by the Win or Jackpot of this set.

Higher Stakes

 At 13th level, you learn to take a high stakes bet and raise the stakes even higher. When you roll an attack with disadvantage (this can be after applying High Stakes) that would apply your Sneak Attack on a hit, you can roll three d20s instead of two and take the lowest of the three. If you do, you deal an additional 3d6 Sneak Attack damage, which stacks with your High Stakes damage.

Russian Roulette

Starting at 17th level, you learn how to risk it all on one deadly spin. As an action, you can choose a creature within 30 feet of you, betting an amount of damage of your choice with must be equal to or less than your current hit points. That creature may choose whether or not to accept, though they must succeed on a Wisdom saving throw (DC equals 8 + your proficiency bonus + your Charisma modifier) when they decline, or else they are forced to accept. If the bet is accepted, roll a d4. On an odd roll, you lose, and on an even roll, the target loses. The loser takes psychic damage equal the amount bet.