Grifter (Rogue Subclass)

You sharpen your deception and acting while engaging in schemes of confidence. Those roguish pickpockets, crooked gamblers, and confidence artists of any stripe- criminals who relied on skill and wits rather than physical violence- are said to be "on the grift."
In addition to your roguish talents, you've learned to charm and seduce your victims into aiding in their own fleecing. Few can match your ability to talk your way into where you don't belong, and out of any trouble that comes your way.

 

 

Fast Talking

When you choose this archetype at 3rd level, you gain the ability to speak with unerring conviction. Whenever you make a Charisma (Deception) or a Charisma (Persuasion) check involving speech, roll the check with advantage.

 

Grifter's Mark

Starting at 3rd level, you've learned how to bait your opponents into a trap with your Sneak Attack. When you hit a creature with your Sneak Attack feature, you can mark the creature until the start of your next turn. This effect ends early if you are incapacitated, you die, or if the target is marked by someone else.

While a creature is marked by you, it has disadvantage on any attack roll that does not target you. In addition, if the marked creature deals damage to you, attacks against the marked creature have advantage until the effect ends.

You can use this feature a number of times equal to your Charisma modifier (minimum of once), and you regain all expended uses of it when you finish a long rest.

 

Flim Flam

By 9th level, your talent for deception makes it difficult for enemies to know how hard they've struck you. When you utilize your Uncanny Dodge feature, and after taking the remaining damage, you can gain the benefits of false life as if it were cast as a 2nd-level spell.

You can use this ability a number of times equal to your Charisma modifier (minimum of one), and regain all uses at the end of a long rest.

Swindle

By 13th level,  Focusing your ability to misdirect your Marks and fleece them of their valuables is as potent as any sneak attack. You gain an additional way to use your Sneak Attack; In lieu of sneak attack damage after a successful melee attack, you can make a Dexterity (Sleight of Hand) check to add or remove one object from your target. Roll your current sneak attack dice and add the numbers rolled to your total, contested by the target's Wisdom (Perception) check.  As an action, you can also use this feature while out of initiative.

Once you use this feature, you cannot use it again until your finish a long rest.

Silver-tongued Liar

When you reach level 17, your ability to convince others is nothing short of magic. As an action, you can cast Mass Suggestion without expending material components. This grifter features require your targets to make a saving throw to resist that feature's effects. The saving throw DC is calculated as follows:

Grifter Save DC =  8 + your proficiency bonus + your Charisma modifier

Once you use this feature, you can't use it again until you finish a long rest.