Courtier
This expert moves in important social circles, but truly excels in the shadows behind the throne. Often working as spies and assassins, a courtier combines the biting eloquence of a noble with the malevolence of a cold-blooded killer.
Recommended Clever Tricks – A courtier will probably benefit most from Analyze, Demoralize, Swindle, and Taunt.
Recommended Discoveries – A courtier will probably benefit most from Deception, Investigation, Stealth, or a language. Those intending to make their own poisons would also benefit from Nature.
Grace
At 1st level, a courtier gains proficiency with dancer’s shoes. If they were already proficient with them, they gain expertise instead.
In addition, they gain the Footwork feature. Unless they are incapacitated or overloaded, they add their proficiency bonus to Defense and initiative checks.
Sneak Attack
Starting at 1st level, a courtier that is not encumbered can strike subtly and decisively.
Once per turn, when they hit an enemy with a light, thrown, or projectile weapon that they are proficient with, they can add 1d6 to the damage roll if they have advantage on the attack roll.
The extra damage dealt by this feature increases by 1d6 when the courtier reaches 3rd level, and again when they reach 6th and 10th levels. This extra damage is cumulative with extra damage gained from other Sneak Attack features.
Assassinate
Starting at 3rd level, a courtier can ruthlessly murder an unsuspecting enemy. They have advantage on attack rolls against enemies that are surprised or charmed by them, and any hit they score against an enemy that is surprised or charmed by them is a critical hit.
Repartee
Starting at 3rd level, when a sentient enemy within 10 yards that the courtier can see makes an ability check, attack roll, or saving throw, the courtier can use a reaction to subtract their Tutelage Die from the enemy’s result. An enemy that can’t hear the courtier or be charmed is immune to this effect.
A courtier can use this feature a number of times equal to their Charisma modifier, and then must finish a short rest before using it again.
Cutting Words
Starting at 6th level, whenever a sentient enemy fails an ability check, attack roll, or saving throw after being subjected to the courtier’s Repartee feature, that enemy takes morale damage equal to the courtier’s Tutelage Die + their Charisma modifier.
If a creature would be reduced to 0 hit points by this damage, they instead subtract the courtier’s Tutelage Die from each ability check, attack roll, and saving throw they make until they finish a short rest without hearing or seeing the courtier.
Razor Wit
Starting at 10th level, a courtier adds their Tutelage Die to saving throws against Charm spells and can’t be charmed by nonmagical means.
In addition, when a sentient enemy attempts to charm a courtier of this level, the courtier can use a reaction to attempt a Charisma (Deception) check against that enemy’s passive Insight.
On a pass, that enemy is charmed by the courtier for 1 minute or until they see the courtier or one of their companions take a hostile action towards them or one of their companions.