Gambler

Some rogues rely on skill. Others rely on preparation. Gamblers trust something far more dangerous—luck.

To a Gambler, every fight is a wager and every victory is a hand won against impossible odds. These rogues flirt with fate, betting everything on a single strike, a desperate escape, or a gamble that should never pay off.

Whether they carry a lucky coin, a marked deck of cards, enchanted dice, or simply an uncanny knack for being in the right place at the right time, Gamblers have learned to bend fortune in their favor. They survive attacks that should have slain them, strike when the odds are stacked against them, and somehow always seem to have one last trick hidden up their sleeve.

As they grow in power, Gamblers learn that luck is more than chance—it is a force that can be manipulated, wagered, and ultimately mastered. By the time they reach the height of their craft, they no longer merely play the game.

They become the dealer.

Level 3: Roll the Bones

At the start of your turn, you can roll your Gambler's Die to determine an effect from the Roll the Bones table. The effect lasts until the start of your next turn.

You can use this feature a number of times equal to your Proficiency Bonus, regaining all expended uses when you finish a Long Rest.

Last Chip. When you roll Initiative and have no uses of Roll the Bones remaining, you regain one expended use of that feature.

Your Gambler's Die begins as a d6.

At 9th level, it becomes a d8 and gains additional results.

At 13th level, it becomes a d10 and gains additional results.

Roll the Bones

d6 Results

Roll	Effect
1 — Snake Eyes	You have Advantage on your next Attack Roll this turn. Attack Rolls against you have Advantage until the start of your next turn.
2 — Lucky Break	You gain a +1d6 bonus to your AC against the next Attack that hits you before the start of your next turn.
3 — Double Down	If you hit with Sneak Attack this turn, add 1d6 damage to it. This damage increases to 2d6 at 9th level, 3d6 at 13th level, and 4d6 at 17th level.
4 — Bluff	You can take the Help action as a Bonus Action this turn.
5 — Hot Streak	You can take the Dash, Disengage, or Hide action as a Bonus Action this turn without expending Cunning Action.
6 — High Roller	Add 1d6 to the damage of the next weapon Attack that hits this turn. At 9th level, this result changes to the High Roller Upgrade.

Additional d8 Results (9th Level)

Roll	Effect
7 — Flashing Steel	When you take the Attack action this turn, you can make one additional weapon attack as part of that action. This attack can't deal Sneak Attack damage.
8 — Jackpot	Regain one expended use of Roll the Bones. Then immediately roll your Gambler's Die again and gain that result. The additional roll can't produce Jackpot. If it does, reroll the die until a different result is rolled.

Additional d10 Results (13th Level)

Roll	Effect
9 — Loaded Hand	Roll the Sneak Attack dice twice and use either total.
10 — Royal Flush	Until the start of your next turn, your weapon attacks score a Critical Hit on a roll of 19 or 20 on the d20. While this effect is active, if you score a Critical Hit, roll your Sneak Attack dice three times and use the highest total.

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Level 3: Gambler's Guile

You gain proficiency in one of the following skills of your choice: Intimidation, Performance, or Persuasion.

If you already have proficiency in the chosen skill, you gain proficiency in another skill of your choice instead.

You also gain proficiency with one Gaming Set of your choice.

Level 9: Luck of the Draw

Roll 1d6.

• On a 1–3, the attack hits normally.

• On a 4–6, the attack misses instead.

If the attack misses, you can immediately move up to half your Speed without provoking Opportunity Attacks.

You can use this feature a number of times equal to your Proficiency Bonus, regaining all expended uses when you finish a Long Rest.

 

Level 9: High Roller Upgrade

High Roller. The next time you score a Critical Hit before the start of your next turn, you roll one additional weapon damage die when determining the damage for that hit.

 

Level 13: House Odds

Immediately after you roll Initiative, choose one of the following wagers. The wager lasts until combat ends.

The House Favors Me

You stack the deck in your favor.

• You have Advantage on Initiative rolls.

• You have Advantage on the first Attack Roll you make during the combat.

If you deal Sneak Attack damage before the end of your second turn in that combat, regain one expended use of Roll the Bones and immediately roll your Gambler's Die without expending a use.

The House Favors Them

You bet against yourself in hopes of a larger payout.

• You gain one additional use of Roll the Bones for the combat.

• Double Down deals an additional 2d6 damage for the duration of the wager.

If you score a Critical Hit during the combat, immediately roll the Bones without expending a use and gain both results.

 

Level 17: The House Always Wins

At the height of your craft, luck is no longer something you chase—it is something you command. Fate bends around your wagers, impossible hands become commonplace, and even death struggles to collect its due. Your mastery of fortune grants you the following benefits.

 

 

Loaded Fate

When you use Roll the Bones, you can roll three Gambler's Dice instead of two and choose which two results to keep.

You can use this feature a number of times equal to your Proficiency Bonus, regaining all expended uses when you finish a Long Rest.

 

Stacked Deck

When you roll doubles naturally while using Roll the Bones, you can change one of those dice to another result available on your Gambler's Die.

 

The House Doesn't Lose

Once per Long Rest, when you would be reduced to 0 Hit Points, you instead drop to 1 Hit Point and immediately roll the Bones without expending a use, gaining both results.

You can't gain more than one additional weapon attack from Roll the Bones on a single turn, even if multiple effects would grant it.

 

Level 17: Dead Man's Hand

When you roll doubles naturally while using Roll the Bones, you can invoke Dead Man's Hand instead of applying those results.

When you do, you gain the following benefits until the end of your turn:

• You have Advantage on Attack Rolls.

• Your weapon attacks score a Critical Hit on a roll of 18–20 on the d20.

• When you deal Sneak Attack damage, you roll the Sneak Attack dice twice and use either total.

This benefit doesn't stack with Loaded Hand.

Once you use this feature, you can't use it again until you finish a Long Rest.

You can't use this feature on a result that you chose or modified using another feature.