Assassin
Medium Humanoid (any race), any non-good alignment
3,900 XP
Special Abilities
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 (1/Turn)
The assassin deals an extra 13 (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 ft. 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 shortsword attacks.
Shortsword
Melee Weapon Attack: +6 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: +6 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.
Quick Reference
Running This Encounter
The Assassin excels at eliminating single targets before combat begins. Use the Assassinate feature to deal massive burst damage on the first round if the party is surprised. Position the assassin in shadows or high ground to maximize advantage rolls. If initial ambush fails, the assassin should use mobility and cunning to pick off isolated party members.
Combat Tactics
The Assassin prioritizes eliminating spellcasters or healers first through hit-and-run tactics. If cornered or facing multiple opponents, it uses Evasion to minimize damage and attempts to break line of sight to set up another ambush. The assassin avoids prolonged melee combat against multiple foes.
Environment & Setting
Urban environments with rooftops, alleyways, and plenty of shadows are ideal. Locations with multiple escape routes and elevated positions give the assassin tactical advantages.