Assassin

A friendly assassin is hired muscle, a contract guildmate, or a rogue PC's cousin. The framing is professional: the assassin is on the party's payroll for one specific job, and the contract terms shape every choice they make at the table.

In combat, the assassin is your strike specialist. Open the encounter on the party's terms by giving the assassin a turn before initiative for one Light Crossbow shot from concealment, taking a key enemy down to Bloodied or below before the fight starts. After that, position the assassin near the squishiest enemy backline and let them shred a caster with three poisoned shortsword attacks per round. Cunning Action means they can Hide between attacks, denying counterstrikes and triggering Sneak-Attack-style anxiety in the enemies even though Sneak Attack isn't on the sheet.

The assassin will not bodyguard the party, will not investigate the moral weight of the contract, and will not stay past the agreed work. If a player tries to talk the assassin into helping with a side quest, the answer is a flat number. If they try to renegotiate after the kill, the assassin renegotiates upward. Have the contract terms written on an index card the players can see at the table. It frames every interaction.

Once the job is done, the assassin leaves the same night. If the party asks for a referral, they get one. If the party tries to keep the assassin around, the assassin politely vanishes and the next time the party hears from them is a bill in a sealed envelope.

Have the assassin name the price before the work, never after. Players accept up-front contracts and resent surprise invoices.

An assassin is a one-round burst dressed up as a person. The whole stat block is built around one ambush, ideally one that you set up across the previous session.

Stage the surprise. The assassin's +10 Stealth and 20 initiative mean it almost always gets the drop, and you should treat the first round as a separate scene from whatever fight follows. Open with a Light Crossbow shot from cover at 80 ft.: +7 to hit, 8 piercing plus 21 poison on a hit. That's enough to drop most squishies in one bolt, and against a sleeping target you should just describe the kill rather than rolling. If the contract is on a PC, telegraph the threat at the end of the previous session so the players have a chance to take precautions. An assassination that comes out of nowhere feels arbitrary; one the party knew was coming and still failed to stop is the campaign moment you want.

Once the surprise round is over, the assassin's job changes from killer to escape artist. Multiattack gives three weapon attacks in any combination, so a melee turn is shortsword spam: +7, 1d6+4 piercing plus 5d6 poison per hit, with a Poisoned condition tacked on. Cunning Action means Hide is a bonus action every round, so a single line of cover plus a successful Stealth check at +10 vanishes the assassin again. Evasion makes any AoE caster's response feel weak. Dexterity 18 plus Evasion against a Fireball is half damage at worst, none on a make.

Run the retreat openly. Assassins do not die for their contracts. Once Bloodied or once the target is down, the assassin Disengages with Cunning Action and uses the next two turns to disappear. The party can chase, but with 30 ft. walk and Hide-on-bonus the chase is rarely fair. The contract was the point; the contract was paid.

Don't say "the assassin attacks." Say what the players see: a window curtain twitches, then a bolt is in the bard's chest. The reveal of the source is what they roll Perception for.