Image promptlean masterful humanoid assassin, dark studded leather armor, twin venom-dripping poisoned daggers, low hood, half-melted into alley shadows, rain-slick city backstreet, rooftops and crowd cover, marking a target, silent predatory crouch, distant lit tavern window, sooty blacks and wet cobble greys, sickly green poison accents, dark fantasy, grimdark, painterly digital art, dramatic chiaroscuro lighting, muted desaturated palette with corrupted-crimson accents, weathered post-Cataclysm atmosphere, intricate high detail, cinematic composition

Guildmaster's Shadow

Medium Humanoid, Neutral Evil
CR 12LurkerSettlement / Road
AC 18 (studded leather +2)
HP 161 (23d8 + 46)
Speed 40 ft., Climb 30 ft.
STR
12
+1
save +1
DEX
22
+6
save +10
CON
14
+2
save +2
INT
16
+3
save +7
WIS
15
+2
save +2
CHA
14
+2
save +2
Skills Acrobatics +10, Deception +6, Perception +6, Sleight of Hand +14, Stealth +14
Resistances Poison
Senses Darkvision 60 ft. (magical); Passive Perception 16
Languages Common, Thieves' Cant, +2 languages

Traits

Evasion. On a DEX save that deals half damage on a success, this creature takes no damage on a success and half on a failure.

Assassin's Mark. During a short rest, chooses a target. Attacks that target with Advantage, and Sneak Attack damage against it increases by +2d6.

Sneak Attack (1/Turn). When attacking with Advantage or when a target has an ally within 5 feet of it: 28 (8d6) extra damage.

Urban Camouflage. In a crowd, shadow, or other urban cover, can take the Hide action as a Bonus Action.

Actions

Multiattack. Makes three Poisoned Blade attacks.

Poisoned Blade. Melee Attack Roll: +10, reach 5 ft. Hit: 10 (1d8 + 6) Piercing damage plus 14 (4d6) Poison damage, and the target makes a DC 16 Constitution save. Failure: The target has the Poisoned condition (1 minute). The target can repeat the save at the end of each of its turns.

Throwing Knife. Ranged Attack Roll: +10, range 20/60 ft. Hit: 10 (1d6 + 6) Piercing damage plus 7 (2d6) Poison damage.

Bonus Actions

Cunning Action. Takes the Dash, Disengage, or Hide action.

Reactions

Uncanny Dodge. When hit by an attack it can see, halves that attack's damage.

How to Use

The head of the assassins' guild. It closes in unseen, marks a target (usually the Wizard) with Assassin's Mark, and erases them in a single turn:

3 attacks × (10 + 14) + Sneak Attack (28 + 2d6 from Mark) = ~110 damage

Key

Not See Invisibility / Truesight — it isn't invisible, it's hiding. High Passive Perception, area spells (Evasion still leaves half damage), or forcing it into open ground (Urban Camouflage stops working).