Gambler

Some Rogues live by wit, others by steel. A Gambler thrives on risk itself, weaving chance into every move. Each toss of the dice could mean ruin or reward, but the Gambler embraces the wager without hesitation.

Credit: Sax Homebrew (Sax-7777299), originally posted to r/UnearthedArcana

Level 3: Ante Up

You have a number of Dice equal to your Charisma modifier (minimum of 1). Once per turn, you can spend a Die immediately before making an attack roll. If you do, roll a d6 and note the result.

Even Number. If the d6 shows an even number, add that result to the attack roll.

Odd Number. If the d6 shows an odd number, subtract that result from the attack roll.

If the attack hits, you deal extra damage equal to half the number of Sneak Attack dice for your level (round up). The extra damage is the same damage type as the weapon's damage.

You can never have more Dice than your Charisma modifier, and you regain all expended Dice when you finish a Short or Long Rest.

Level 3: Bluff

Select one Gaming Set, as well as one skill from the following list: Deception, Persuasion, or Sleight of Hand. You gain proficiency with each choice. If you already have proficiency, you gain Expertise instead.

Level 9: Loaded Dice

When the die you roll for Ante Up shows an odd number, you can choose to increase that number by 1 and treat it as even.

Once you use this feature, you can't do so again until you finish a Short or Long Rest.

Level 9: The House Always Wins

Whenever you reduce a hostile creature to 0 Hit Points or score a critical hit against one, you regain 1 Die. You can benefit from this feature only once per turn.

Level 13: Slots

At the start of your turn, you can spend 1 Die to spin the reels of fate. Roll a number of d6s equal to your Charisma modifier (minimum of one). For each die that shows a 6, you gain one of the following effects of your choice. You cannot choose the same effect more than once on a turn.

High Roller. You have Advantage on the next D20 Test you make before the start of your next turn.

Hot Streak. Your Speed is doubled until the start of your next turn.

Insurance. You gain Temporary Hit Points equal to your Rogue level.

On The House. The next time you use Cunning Strike before the start of your next turn, the number of Sneak Attack dice you forgo for one option is halved (round down).

Hit. You regain 2 Dice.

Level 17: All In

When you use Ante Up, you can choose to go 'All In' by spending all your remaining Dice. When you do, roll a d10 instead of a d6. If the attack hits, the extra damage granted by Ante Up uses d10s instead of your Sneak Attack dice.

If this damage reduces the target to 0 Hit Points, you regain a number of Dice equal to twice the number you spent. If this would cause you to exceed the maximum number of Dice you can hold at one time, you can trigger Jackpot.

Jackpot. Roll a number of d10s equal to the number of excess Dice granted by All In. Each creature of your choice that you can see within 30 feet of the target takes Force damage equal to the result.

Once you use this feature, you can't do so again until you finish a Short or Long Rest.