Gambler

The gambler is a deviant who has honed his skill at the table and turned it into a deadly art of pressing advantage and knowing when to hold back. Those who model themselves after this archetype combine luck with skill to gain the upper hand over their adversaries and to line their pockets.

Game Master

Starting at 3rd level, your time spent in back rooms and alleys swindling folk has resulted in an above average aptitude for gaming. You gain proficiency in any two gaming sets.

Additionally, you choose one gaming set you are proficient in and may add double your proficiency bonus to checks made using that set.

Fate or Fold

Also, starting at 3rd level, you’ve become adept at predicting the outcome of any situation and exploiting that knowledge.

Before making an attack roll, saving throw, or ability check you can use your reaction to predict that it will be a success.  Depending on the type of roll, you gain the following benefits if your prediction comes true.

Attack. You qualify for sneak attack on this attack without needing advantage and deal an additional 1d6 damage with the sneak attack feature. This bonus increases to 2d6 at 13th level.

Saving Throw. You ignore all effects from the saving throw as if you were not targeted by it.

Ability Check. You gain advantage on all checks of the same skill for the next minute, or until you fail a check of that skill.

You may only take this reaction a number of times equal to your Charisma modifier (minimum 1). You recover all uses of this feature after completing a short or long rest.

Risk and Reward

Starting at 9th level, you’ve come to take risks when you have the upper hand against your foes.

Whenever you roll additional damage for sneak attack, you can choose to remove two dice from the sneak attack damage and roll them separately. You do not add these dice to your damage, but instead apply a modifier to your damage roll depending on their results.

Snake Eyes. (both dice show 1s). Your attack deals no damage and is considered a miss, even if it was a critical hit.

Lucky Seven. (the total of both dice is equal to 7). Your attack deals additional damage equal to twice the result of the higher of the two dice.

Double Sixes. (both dice show 6s). You add the result of this roll to your damage and then double all damage dealt by this attack.

Rig the Game

Once you’ve reached 13th level, you can ensure the odds are in your favor with a gaming set.

You can alter a single gaming set of your choice to work to your advantage. You must spend at least 1 hour in solitude with the gaming set to do so. You can only have one altered gaming set on your person at any given time. Anyone who spends 1 minute uninterrupted investigating an altered gaming set will know it is rigged.

Any time you participate in an ability check or contest with this gaming set, you have advantage. In addition, if you succeed in a contest using this gaming set you can immediately perform one of the actions listed below as a reaction.

Coup de Grace. Your victory awards you an opportunity to attack your opponent. They must make a Dexterity saving throw with a DC equal to 10 + your Sleight of Hand bonus. You deal piercing damage equal to your sneak attack damage as shown in the Sneak Attack column of the Rogue table on a failed saving throw, or half as much on a successful one. If that creature was not already hostile towards you, it immediately regards you as a threat.

Collect the Pot. Your success has resulted in a prize. You can ask your opponent any one question and they must answer truthfully to the best of their knowledge.

Bravado. You hold your head up high and your success over your opponent. You have advantage on all social interactions with your opponent for the next hour.

Overcome Odds

At 17th level, your ability to capitalize on the advantage and  benefit where others would fail has helped to ensure your
success in most things.

Whenever you make an attack roll, saving throw, or ability check with either advantage or disadvantage, if both die show the same result and aren’t 1s you automatically succeed the roll regardless of the result.