Grand Master Assassin

Medium humanoid (any race), any alignment

Armor Class 17 (studded leather)
Hit Points 104 (16d8 + 32)
Speed 35 ft.

STR	DEX	CON	INT	WIS	CHA
13 (+1)	20 (+5)	15 (+2)	15 (+2)	16 (+3)	16 (+3)

Saving Throws Dexterity +9, Intelligence +6, Wisdom +7
Skills Athletics +5, Acrobatics +10, Deception +7, Insight +7, Investigation +6, Perception +11, Sleight of Hand +9, Stealth +13
Senses blindsight 10 ft., passive Perception 21
Languages Thieves’ Cant plus any three languages
Challenge 14 (11,500 XP)

Special Traits

• Assassinate. During its first turn, the grand master assassin has advantage on attack rolls against any creature that hasn’t yet acted in the combat. Any hit the grand master assassin scores against a surprised creature counts as a critical hit.
• Cunning Action. On each of its turns, the grand master assassin can use a bonus action to take the Dash, Disengage, or Hide action.
• Evasion. If the grand master assassin is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, the grand master assassin instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.
• Practiced Impersonator. The grand master assassin has advantage on any Intelligence ability check to disguise themselves.
• Sneak Attack (1/turn). Once per turn, the grand master assassin deals an extra 31 (9d6) damage when it hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the grand master assassin that isn’t incapacitated and the grand master assassin doesn’t have disadvantage on the attack roll.

Actions

• Multiattack. The grand master assassin makes two Rapier attacks or two Dagger attacks.
• Dagger. Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4 + 5) piercing damage.
• Shortsword. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 5) piercing damage.
• Light Crossbow. Ranged Weapon Attack: +9 to hit, range 80/320 ft., one target. Hit: 9 (1d8 + 5) piercing damage.

Legendary Actions

The grand master assassin can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. The grand master assassin regains spent legendary actions at the start of its turn.

• Grasp the Advantage. The grand master assassin makes one rapier or dagger attack on a creature within range that has made an attack this round.
• Poison Weapon (costs 2 actions). The next melee or ranged weapon attack the grand master assassin makes is poisoned, and the target that takes damage from it must make a DC 15 Constitution saving throw. On a failed saving throw, the target takes 24 (7d6) poison damage, or half as much damage on a successful saving throw.