The Cardsharp
Overview on Creating
Inveterate gamblers, cardsharps are rogues who thrive on risk, danger, and threat. They use table tricks, sleight of hand, and targeted deceptions to keep their foes off balance and themselves on top. Their advantages are not without drawbacks, but win or lose, you can always count on a cardsharp to raise the stakes.
Subclass Features
Ante Up
3rd-level Cardsharp feature
You are most comfortable at a gambling table. You gain Proficiency in the Insight and Sleight of Hand skills if you don't have them already, as well as with two gaming sets of your choice. You have Advantage on any ability check which uses these Proficiencies.
Additionally, you may add your Dexterity modifier to any ability check which uses the Deception or Performance skills, provided you have a gaming set in your hand.
Double Down
3rd-level Cardsharp feature
When the stakes are highest, you reach for more. If you make an attack roll against a creature that has dealt damage to you since the end of your last turn, you can use your Sneak Attack when the attack hits, even if there are no other creatures within 5 feet of the target and you don't have Advantage on the roll. You cannot use this feature if you have Disadvantage on the roll.
When you hit a creature in this way and deal Sneak Attack damage, you can potentially increase that damage by gambling on it. To do so, roll 1d6 immediately after hitting with an attack roll, and subtract 3 from the number rolled. The total is the number of additional Sneak Attack damage dice you add to your damage roll. This feature can reduce the number of Sneak Attack damage dice you roll when you hit. Additional damage dealt is the same as the weapon's type.
Fold
3rd-level Cardsharp feature
Sometimes, you just have to know when to quit. When you miss with an attack roll, you gain the benefits of the Disengage and Dash actions until the end of your current turn.
Art Credit: "The Card Game" by Magnus Noren via ArtStation
Poker Face
9th-level Cardsharp feature
You are incredibly hard to read. You have resistance to Psychic damage, as well as Advantage on any saving throws you make against effects which would read your mind or deal Psychic damage to you, such as the Detect Thoughts or Vicious Mockery spells.
Additionally, ability checks made to determine your intentions or truthfulness have Disadvantage, and you are immune to the Zone of Truth spell.
Blackjack
13th-level Cardsharp feature
You gain the following Cunning Strike option:
Bust (Cost: 2d6). Roll 1d20+1. If your total roll is lower than or equal to the target's AC, attack rolls against the target still deal half damage, even on a miss, until the start of your next turn.
An Ace Up the Sleeve
17th-level Cardsharp feature
The dealer is not always on your side, and you have learned to be prepared. When you finish a long rest, roll three d20s and record the numbers rolled. When a creature which you can see rolls a d20 Test, you can choose to replace their d20 roll with one of these ace rolls. You can do so after the roll, but before its effects are resolved.
Each ace roll can be used only once. When you finish a long rest, you lose any unused ace rolls.

