Grifter

You teach yourself the art of the confidence trick, allowing you to take advantage of your enemy's confidence and twist it to your advantage. While all rogues understand some variety of deception, you focus on how to start and maintain fraudulent exchanges which benefit you. Most conmen, political manipulators, and even a large variety of businessmen use this archetype. Knowing how to make your enemy want what benefits you will allow you to manipulate your way to success.

Exploit Confidence

 If a creature has advantage on attack roll against you or an allied creature or if they have been granted advantage on a saving throw, you have advantage on both attack rolls and skill checks against them.

Marks

When you select this archetype at 3rd level, you gain the ability to designate targets as a mark for your cons. You gain a number of Mark Points equal to your proficiency bonus, and you may use your action to either use one to mark a creature you can see for a short con or two points to mark them for a long con. While an enemy is marked for a con, you have advantage on all Charisma checks as well as Dexterity (Sleight of Hand) checks. This advantage lasts for one hour for short cons or for one day for long cons; unless you end it early as a bonus action. Once a con ends, you may use a mark point to make a Charisma (Deception) check against the target's passive insight score to refresh the con's duration. If the check fails or if you do not make a check, the target becomes aware that they are being defrauded. You regain all mark points after taking a long rest.

Preliminary Research

At 9th level you learn how to prepare for cons and know your targets. If you spend at least six hours researching a target, you may mark them without using a mark point, and your checks to extend the mark are made at advantage and you do not need to spend a mark point to do so.

Shocking Reveal

At 13th level, you learn how to keep your victims in shock while you make your escape. Once you end a con after it has been renewed at least once, the target has disadvantage on all Intelligence, Wisdom, and Charisma checks and saving throws for the next minute. This only works if the con can see you while you end it.

Unmatched Swindler

At 17th level, you become an expert in all forms of deception. If you make a deception check, you may use a mark point to add 10 to the roll before you learn if the roll has succeeded or failed, but after you see the number you have rolled.