Bandit Captain

Hiring a bandit captain is one of the better non-magical upgrades a mid-level party can buy, and the negotiation is half the fun. The captain works for coin, leverage, or a shared enemy, in roughly that order. The party isn't friends with this person and shouldn't be; they're partners in a contract that has an expiration date both sides are watching.

In a fight, the captain runs the captain's playbook with the party as the line. Pistol the priority target the party calls (or the one the captain decides to undercut, depending on how clean the contract is), then close with Scimitar. Parry stays available for whichever PC is taking the worst beating, since dead clients don't pay. The captain expects the party to absorb hits; the captain is the finisher, not the tank, and 52 HP plus AC 15 disappears fast against anything with multiattack.

The captain's loyalty has a price tag stapled to it. If the contract goes long, they renegotiate. If the party tries to stiff them, they walk, and the next time the party meets them they're working for the other side. Deception +4 means they're lying about something at all times: the size of the cut their crew expects, the favor they actually owe in town, the reason they took the job in the first place. None of this should derail; all of it should season.

Roll the captain's secondary motive once at hire and write it on a card. Revenge against a noble, a sister to ransom back, a debt to a hag. Reveal it under pressure.

A bandit captain is the named NPC at the center of a bandit encounter, and that's how you should design every fight involving one. Solo, the captain is a mid-tier brawler with 52 HP and Parry; in a group of mooks, the captain is the reason the mooks haven't already run. The party should know the captain's name before initiative, ideally because someone in town spat it on the floor.

In combat, the captain has Multiattack with Scimitar plus Pistol in any combination. The right opener is one Pistol shot at the squishiest range threat (cleric, sorcerer, archer) at +5 to hit for 8 average, then close to scimitar range on the bonus action's worth of movement. Pistol again next round if the target is still standing back, otherwise two scimitars at +5 for 6 each. Parry is the captain's signature: when the front-line PC connects, add 2 to AC against that one attack. Use it on the crit, not the standard hit. A captain who Parries a 22 looks like a duelist; a captain who Parries a 14 wastes the reaction.

The captain leads. While the captain is up, the bandits hold the line, take Help actions to set up the captain's Pistol, and refuse to break. The moment the captain drops, the rest test morale and most of them flee. Lean on this. A party that learns to focus the captain learns the right lesson about command structure, and a party that ignores the captain spends three rounds chewing on hit points.

Captains negotiate when they're bloodied. They want to live and they want most of their crew to live, and they will give up the cart, the route, and the name of their employer to walk out alive. Have the captain offer a deal in character before the killing blow. A bandit captain who becomes a recurring informant is worth more than a corpse.