Assassin, Boss

Medium Humanoid (any race), Any non-good alignment

Armor Class 16

16 Hit Points 112

112 Speed 30 ft

STR DEX CON INT WIS CHA 11 (+0) 16 (+3) 14 (+2) 13 (+1) 11 (+0) 10 (+0)

Saving Throws DEX +6, INT +4

DEX +6, INT +4 Skills Acrobatics +6, Deception +3, Perception +3, Stealth +9

+6, Deception +3, Perception +3, Stealth +9 Damage Resistances Poison

Poison Senses Passive Perception 13

Passive Perception 13 Languages Thieves' cant plus any two languages

Thieves' cant plus any two languages Challenge 9 (5,000 XP)

Assassinate. During its first turn, the assassin has advantage on attack rolls against any creature that hasn't taken a turn. Any hit the assassin scores against a surprised creature is a critical hit.

Evasion. If the assassin is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, the assassin instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.

Sneak Attack. Once per turn, the assassin deals an extra 14 (4d6) 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 assassin that isn't incapacitated and the assassin doesn't have disadvantage on the attack roll.

Actions Multiattack The assassin makes two attacks with their shortsword. They can substitute one of these attacks with an attack from their light crossbow. Shortsword. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 6 (1d6 + 3) piercing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one. Light Crossbow. Ranged Weapon Attack: +7 to hit, range 80/320 ft., one target. Hit: 7 (1d8 + 3) piercing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.

Bonus Actions Now! When the Assassin attacks an enemy on their turn, they can use a bonus action to grant one of their allies adjacent to that enemy an attack on that enemy.

Reactions Trained Reflexes. The Assassin gets two reactions per round. Killing Spree. When the Assassin knocks an enemy unconscious, they can spend their reaction to move up to their speed. This movement does not provoke attacks of opportunity.