Gambler

Gambler rogues are masters of sleight of hand trickery, and use their sheer dumb luck to succeed in ways that no other type of rogue can.

Truth seeker

When you take this subclass at 3rd level, your gambling skill gives you the ability to see through lies, giving you advantage on insight checks.

Card counter

Also when you take this subclass at third level, your skill with gambling equipment gives you an interesting ability to use that equipment in ways that defy logic. You can attack with cards or die as a bonus action on your turn, this attack deals 1d6 damage, either slashing (cards) or bludgeoning (die). The range for this attack is 60/120.

Gambler’s luck

You seem to have an endless amount of luck, starting at 9th level, whenever you roll a Natural 1 on an attack roll, ability check, or saving throw, you can reroll, you must use the new roll and you cannot have advantage or disadvantage on this roll. You can use this ability as many times per long rest equal to your charisma modifier.

Bluff

Your bluffing skill gives you an edge in deception. Beginning at 13th level when an attempt is made to discern any kind of bluff you make, including lying or omitting information, the roll is make with disadvantage. Additionally you can make attack rolls at high-stakes. These can only be made if you don’t have advantage or disadvantage on the attack roll. When you roll this way you roll 2 d20s and take the roll farthest from 10. In the event both numbers are equidistant from 10, you take the higher number. In the event you roll a critical failure, you take the attacks damage instead. When you take this damage you include sneak attacks damage.

Major gamble

You have learned the ultimate gamble, at 17th level you learn the ability to turn attacks into devastating blows. Once per short or long rest when you make an attack that also deals sneak attack damage, you can forgo all damage done by the attack to instead deal 1 d100 damage. Any damage done by this attack is the same as the original attacks. If you roll a one on this die, roll again. This damage is dealt to you instead and you take one level of exhaustion.