Swindler

As a Swindler, you excel in convincing others to do what you want, usually through a careful blend of the truth and well-crafted lies. You rely on your silver tongue over a blade or pistol, though you’re more than capable of getting your hands dirty when things go south.

You Win Some, You Lose Some

When you choose this archetype at 3rd level, you develop a talent for single-handedly convincing others. Whenever you make a Deception or Persuasion check without an ally within 5 feet or receiving the Help action, treat a roll of 7 or lower on the d20 as an 8.

Also at 3rd level, you hone your instincts for swiftly dealing with situations that turn bad. Whenever combat begins as a result of you failing a Deception or Persuasion check with one or more creatures, you are always able to use your Sneak Attack ability against those creatures during the first round of combat. This allows you to use your sneak attack multiple times during that turn, but only once against each of those individual opponents.

Short Con

At 9th level, you gain the ability to use choice words laced with truth and lies to make a marked individual lose confidence in their abilities. As an action you can mark a target within 30 feet who can hear you, causing them to make any Wisdom saving throws at disadvantage for the duration of the short con. The short con lasts for 1 minute or until you fail a Charisma check against them.

On subsequent turns, you can use a bonus action to reinforce the short con against your mark. Roll your choice of a Deception or Persuasion skill check. The target of your mark must roll a Wisdom saving throw at DC equal to your Deception or Persuasion roll. On a success, choose an additional ability saving throw which they now also roll at disadvantage for the duration of the short con. With the con successfully reinforced, the duration resets to 1 minute. On a failure, they immediately get wise to your con and the short con ends.

Long Con

At 13th level, you have mastered the art of weaving more elaborate cons over an extended period of time. If you spend six hours observing and interacting with a potential mark, they gain disadvantage on all Wisdom skill checks and Wisdom saving throws for the duration of the long con. The long con lasts indefinitely provided that you spend at least 30 minutes interacting with mark each day to reinforce the con.

On subsequent days, in addition to any time spent reinforcing your long con, you can spend an additional hour observing and interacting with your mark. At the end of this time, roll your choice of a Deception or Persuasion skill check. The target of your mark must roll a Wisdom saving throw at DC equal to your Deception or Persuasion roll. On a success, choose an additional ability which they now also have disadvantage with on skill checks and saving throws for the duration of the long con. On a failure, they lose confidence in you, causing the last ability you compromised to no long be rolled at disadvantage. If this results in their Wisdom no longer being rolled at disadvantage, the long con ends.

You can choose to convert your long con into a short con. If so, they keep their disadvantage on the ability checks and saving throws affected by the long con but bonus actions taken with the Short Con ability will only affect saving throws with the ability chosen, not ability checks. If the short con ends, the effects of both your short con and the initial long con are ended.

Gift of the Gab

Beginning at 17th level, your silver tongue is unrivalled. If you fail a Charisma ability check, you can roll it again with advantage. Once you do so, you can’t use this feature again until you finish a short or long rest.

In addition, your You Win Some ability is improved so that when making a Deception or Persuasion check, a roll of 11 or lower on the d20 is treated as a 12. The additional conditions for using that ability are also ignored.