College of the Sanguine Masquerade

Bards of the Sanguine Masquerade are assassins that utilise the feats of common court fools and carnival entertainers to eliminate targets without arousing suspicion. Card gambits and palm readings provide ample distraction for the administering of poisons, while a silver tongue serves well for the purpose of infiltration and espionage. Cunning killers without peer, these bards excel in utilising a target's own indifference to get within striking distance, while their penchant for tumbling and gambolling provides them with a convenient means of egress and pursuit. Most of all, bards of the Sanguine Masquerade specialise in the art of throwing weapons, which they utilise with deadly accuracy, staggering volume, and undeniable style.

Play the Fool

At 3rd level, your seemingly harmless panache for acrobatics and gambolling actually provides you with effective means to close the distance with your marks, and flee your pursuers. As a bonus action, you may tumble. If you do so, you may move up to half your movement speed without provoking attacks of opportunity. In addition, until the end of your turn you take half damage from falling, and gain a climbing speed equal to your movement speed. If you end your movement on a sheer surface with no available handholds, you will fall at the start of your next turn.

Furthermore, your experience in playing the fool often means that your foes are left unaware of your true intentions. You gain proficiency in Deception and Sleight of Hand. In addition, whenever you make a Charisma (Deception) or Dexterity (Sleight of Hand) check, before the result is declared, you may expend one of your Bardic Inspiration dice to add it to the total of the roll.

Whirling Steel

At 3rd level, you have honed your mastery of thrown weapons to a lethal point. When utilising thrown weapons, you gain a +2 to attack and damage rolls with them, and may draw and throw them as a part of the same action. This does not stack with the Archery and Thrown Weapon fighting styles.

Fan of Blades

Beginning at 6th level, you can attack twice, instead of once, whenever you take the Attack action on your turn provided that you are only using throwing weapons for these attacks. In addition, you may take a -5 penalty to each attack you make on your turn to make one further additional attack with a throwing weapon as a part of the same attack action. This ability does not stack with Extra attack.

Misdirection

At 6th level, you know how to disguise lethal intent behind a masque of slapstick clumsiness, turning potentially lethal attacks away from you, and back at your foes. When a creature makes an attack against you, you may expend one Bardic Inspiration die, and add the number rolled to your armor class until the end of the attacking creature's turn. If an attacking creature misses you before the end of their turn, you may use your reaction to have them re-roll that attack against an enemy creature within 5 feet of you.  If the attacking creature is within 5 feet of you, you may force them to target themselves with their own attack.

Finale

At 14th level, you have mastered the art of playing into the overconfidence of an enemy, allowing you to use even grievous wounds you have sustained to your advantage. Whenever you suffer a critical hit, you regain 1 of your expended Bardic Inspiration dice. When you score a critical hit against an enemy, you may expend any number of your available Bardic Inspiration dice and add them to the damage roll.