Assassin, Boss

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

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• Armor Class 16
• Hit Points 112
• Speed 30 ft

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

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• Saving Throws DEX +6, INT +4
• Skills Acrobatics +6, Deception +3, Perception +3, Stealth +9
• Damage Resistances Poison
• Senses Passive Perception 13
• Languages Thieves' cant plus any two languages
• Challenge 9 (5,000 XP)

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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.

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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.

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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.

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Villain Actions

The Assassin has three Villain Actions, keyed to rounds in a combat encounter. Villain Actions can be taken at the end of a hero's turn on the appropriate round.

Round 1: To the Mists! The Assassin and all allies can move up to their speed.

Round 2: Fire! All allies of the Assassin may make a ranged attack, if they have one. These coordinated attacks ignore disadvantage from obscuration.

Round 3: Find their weak spots. Any attack made by the allies of the Assassin on their next turn have advantage.

Round 4+ After round three, the Assassin alternates between To the Mists! and Fire! each round.

The Encounter

The Assassin has a magic item, a Cube of Heavy Fog (detailed in the Loot section below), which they use a minute or two before combat begins, covering an area in heavy fog. This works best as a random encounter when the party is already traversing a foggy area, lest the sudden fog seem suspect. The Assassin is joined by 4 Spies (MM, p.350) .

They will attempt to surprise the party, heavily obscured in the fog. Within the fog, objects are heavily obscured more than 10 feet from the viewer. To avoid surprise, a party member must succeed on a DC17 Wisdom (Perception) check. If the area is otherwise free of fog, the check is automatically passed (or made easier, at the DM's Discretion).

Once the battle begins, the spies prefer to attack, use their Bonus Action to disengage, and retreat into the mists. The Assassin tries to stay in the mists until he can get a sneak attack.