Gambler

These cunning individuals have learned the value in a lucky streak. They have learned ways to push the odds in their favor, but also have learned to deal with the consequences when lady luck leaves the table for a moment.

High Roller

At 3rd level gain 2 luck points that function in the same way as the Lucky feat. Whenever you make an attack roll, ability check, or saving throw, you may spend 1 luck point to roll an additional d20. You can use this ability after the original roll, but before the outcome is revealed. You choose which of the d20s is used for the attack roll, ability check, or saving throw.

You can also spend one luck point when an attack roll is made against you. Roll a d20, and choose whether the attacker's roll uses their d20 roll or yours.

If multiple creatures use a luck point on the same roll, they cancel out, resulting in no additional dice.

You regain expended luck points when you finish a long rest. You gain an additional luck point each time you gain a roguish archetype feature.

(This for your DMs to decide, but if a player chooses this subclass at my table, the are prohibited from choosing the Lucky feat).

You also gain expertise in one skill of your choice from Insight, Slight of hand and Deception. You gain proficiency in the two unchosen skills. (I am having trouble figuring out how to display the choice for these three skills as you make your character. So you will have to add the expertise for you chosen skill manually using the "customize" option on your character sheet. Your unchosen skills will add the proficiency automatically).

Cards on the Table

At 9th level you have gotten so good at reading people and situations that as an action you can make an Insight check on an enemy creature. The DC varies based on the challenge rating of the creature.

0-1 = DC 10

2-5 = DC 15

6-10 = DC 20

11-15 = DC 25

16-20 = DC 30

21-23 = DC 35

24-30 = DC 37

On a success you learn the targets Damage Vulnerabilities, Damage Resistances, Damage Immunities, Condition Immunities, Armor Class and current Health Points. On a failure you learn nothing.

You can do this an amount of times equal to your WIS modifier (minimum of one) until you complete a long rest.

Deadman's Wager

When making an attack against a creature, you can choose to take a -5 penalty to the attack roll. If the attack hits it is an automatic critical hit. If you miss, and the target hits your armor class on its next attack, his attack is an automatic critical hit.

You can make this wager as many times as half your proficiency bonus.

Royal Flush

At 17th level you have learned a great fighting technique that is difficult to complete perfectly.

As an action you can attack a creature five times. On each successful hit you add one additional die of the weapons' damage type to the damage for that attack. Also on each successful hit the targets AC goes up by one for the following attacks. If you manage to hit the target with all five attacks, the final attack is an automatic critical hit.

You can preform this technique once until you take a long rest.