Gambler

Most rogues find themselves in risky situations, whether they are trying to sneak into a guarded palace, trying to gaslight investigators, or scouting out an enemy's camp. While most rogues try to mitigate as many risks as possible to avoid mistakes, there are some who instead throw caution to the wind and dive straight into danger, sometimes without a plan and every intention to improvise as they go. Such rogues are typically referred to as "gamblers," named after their preference to gamble their fates as regularly as a commoner visits the local tavern, and somehow know how to make the most out of that gamble.

Level 3: Gambler's Tools

You gain proficiency in two gaming sets of your choice, along with the two physical sets.

Level 3: Stack the Odds

You have a knack for subtly stacking the odds in your favor, regardless of whether they were for or against you to begin with. Whenever you roll more than one d20 during a d20 test, you can reroll the die with the lowest result and choose which result to use for the d20 test.

Level 3: Gambler's Spirit

Creating opportunities and taking risks is more natural to you than safer decisions. You get a pool of gamble points equal to the number of d6s you roll when you deal Sneak Attack damage. Whenever you make an attack roll or an ability check for a skill that you are proficient in, you can spend a gamble point to grant yourself advantage on the roll.

You regain all expended gamble points whenever you finish a long rest. Alternatively, whenever you make a d20 test, you can give yourself disadvantage on the roll in order to regain one gamble point.

Level 9: Rewarded by Risk

Your risky nature grants you the following Cunning Strike option:

Gamble (Cost: 1d6). Before rolling damage, roll a d6 and add your rogue level to the roll. If the result equals or exceeds the AC of the creature you hit, roll your damage as if you had landed a critical hit. You may spend gamble points to roll additional d6s, one for each gamble point you spend.

Level 13: Master Gambler

Your gambling spirit has grown to affect your reflexes and improve your odds when taking greater risks. You gain the following benefits:

Saving Throw Gamble. Whenever you are forced to make a saving throw, you can spend a gamble point to gain advantage on the roll.

Improved Chances. Whenever you have disadvantage on an ability check or saving throw, the DC required for you to succeed is decreased by 5. It is not decreased for other creatures.

Level 17: Go Big or Go Home

Your gambling addiction has led you to learn a secret combat technique that involves imposing a handicap to yourself in order to potentially get a bigger payout. If you take the attack action and don't have either advantage or disadvantage on the attack roll, you can impose disadvantage on the roll. If you still hit with the attack, you get to deal Sneak Attack damage, treat the hit as a critical hit, and double the amount of damage you deal to the creature you hit.

You can use this feature once per long rest without suffering any consequences. Whenever you use this feature more than once per long rest, you must either spend two gamble points or gain a point of exhaustion before you make the attack.