Rake

Every rogue is a trickster and a scoundrel, but very few have the unmitigated audacity to brag about it to potential marks. The Rake is just such an exception, and delights in flaunting their duplicitous nature before snatching the purses of their captivated audience.

Rakes are Charisma-focused Rogues that use charm and audacity to lead their opponents to ruin.

Evasive Rhetoric

When you choose this archetype at 3rd level, you become fluent in two additional languages of your choice.

Your conversational wit continues to be an asset even in pitched combat. As a free action on your turn, you may engage a creature in conversation if it understands the language you are speaking. That creature cannot make Opportunity Attacks this round. You may use this feature only once per round.

Rakish Audacity

Also starting at 3rd level, your confidence propels you into battle. You add your Charisma modifier to your Initiative rolls.

In addition, you may use your Bonus Action to Insult a creature that can hear and understand you. Rakes have Advantage when attacking Insulted creatures, and when making Charisma (Deception) checks against them. However, creatures lose the Insulted condition as soon as they deal damage to the Rake that Insulted them, or when they complete a long rest.

You may Insult creatures outside of combat, but doing so lowers their disposition towards you by one degree: from friendly to indifferent, and from indifferent to hostile. Hostile creatures that you Insult must succeed on a Wisdom saving throw to not attack you immediately (DC 8 plus your Charisma modifier and Proficiency Bonus).

Taunting Strike

At 9th level, you gain a new Cunning Strike option called Taunting Strike (Cost: 1d6): The target becomes Insulted, if it wasn’t already, and has Disadvantage on all attacks against creatures other than you until its Insulted condition ends. You may use Taunting Strike and Withdraw on the same Sneak Attack at the cost of 2d6 damage.

In addition, creatures that you Insult outside of combat do not lower their disposition towards you if you roll higher on a Charisma Ability check than they do on a Wisdom (Insight) check.

Life of the Party

Starting at 13th level, you learn how to fade from center stage to backdrop at a moment’s notice. After publicly announcing your arrival to a peaceful gathering of 10 or more creatures, you may become Invisible. This invisibility ends if you deal damage to a creature, force a creature to make a saving throw, leave the gathering, or when the gathering ends, whichever comes first. You may not use this feature multiple times during the same gathering.

Injury to Insult

Beginning at 17th level, you learn to serrate your sneak attacks with vicious words that cut deep into your enemies’ hearts. When you deal Sneak Attack damage to an Insulted creature, you may force that creature to make a Wisdom saving throw (DC 8 plus your Charisma modifier and Proficiency Bonus). If their save fails, then the target is Stunned until the end of your next turn, but they cannot be Stunned by this feature again until they have completed a long rest.