Scoundrel

Scoundrels are charming, rakish, and usually lying through their teeth. To them society is just propaganda and tradition is only peer pressure from dead people. These scouts forge their own paths, refuse to be tied down, and know that rules are made to be broken. Everybody’s got to eat though, which often puts the fiercely independent scoundrel at odds with authorities—thankfully they know to run when the chips are down, and with a quip and a smile can suavely flip even the worst situations to their benefit.

Honest Face

At 3rd level when you choose this archetype, you gain an expertise die on Charisma checks. In addition, you can use Dastardly Gambit on yourself when making a Charisma check, adding the result of the die to your check.

Fiercely Independent

Also at 3rd level, you become adept at escaping even the most precarious circumstances and your individualist attitude is almost infectious. You gain the following benefits:

• You can use the Disengage action as a bonus action.
• You have advantage on checks and saving throws made to escape a grapple.
• You have advantage on Charisma checks made to dissuade a creature from following orders, to sow discord amidst an organization, or otherwise disrupt a group of cooperators.

Just a Misunderstanding

Beginning at 6th level, you develop a talent for spinning even the most ludicrous circumstances into plausible stories. Whenever you add a Dastardly Gambit die to a Charisma check made to influence a hostile creature, that creature’s attitude to you is treated as if it were indifferent even if you or your allies were previously or are currently fighting it. Any past attacks or aggressive actions are woven into your strangely credible version of events that eases over blame, but this does not forgive future attacks or aggressive actions taken after you use this feature.

Defector’s Spark

Starting at 14th level, you’ve learned just the right words to get people to cast off their shackles and rebel. As an action, you may choose a hostile creature that is operating under the command of another creature that is hostile to you. So long as the target is able to hear you, of a Challenge Rating 5 below your level, and can understand a language that you speak, it makes a Charisma saving throw against your clever tricks save DC. On a failed save the target is convinced to change sides and becomes an ally to you and your other allies, even becoming hostile to its former allies. The chosen creature is not under your control and may change its attitudes later depending on your actions or the actions of your allies. This is not a charm effect. Once you use this feature, you cannot do so again until after you finish a long rest.