Pirate Captain

A pirate captain ally is a hire, a temporary alliance against a shared enemy, or a former rival who owes the party a favor and is paying it off in cutlass. The captain is not a friend. They are a professional, and professionals stay professional as long as the contract is clear. Make the deal explicit before any fight: percentage of the take, route home, what counts as the job being done.

In combat run the captain like a fencer the party gets to point at things. The opening Pistol shot from 30 feet at the enemy caster is the move, and the party should know in advance that this is what the captain does first. After that, three attacks per round at +7 for 13 to 15 each, with the Rapier-into-Advantage combo if the first hit lands. Captain's Charm at DC 14 is a bonus action soft-control that can shut down an enemy commander for a round, and Riposte gives the captain a free swing at any enemy who closes carelessly.

The captain refuses any fight that does not pay. A bandit roadblock is dealt with in three rounds. A patron's pet doom-cult that the party has been warned about by a local oracle gets a polite "no" and a recommendation that the party hire someone who specializes. The captain has a ship and a crew, and the crew expects to drink in the next port. Anything that endangers the ship is off the table.

The exit is the contract closing. Once the agreed thing is done, the captain calls for a round of drinks, takes their cut, and is gone by morning. If the party tries to extend the engagement without renegotiating, the captain charges twice the original rate and means it.

A pirate captain is a duelist with a pistol and a personality. Initiative +7 means they almost always go first, and the opening round should establish that this is not a brawler. Open with one Pistol shot from 30 feet at the squishiest target (+7 to hit, 15 average piercing), then close to rapier range with the remaining movement. The party should know that this captain has a gun before the fight, because guns change how players think about cover.

Multiattack is three attacks in any combination of Rapier and Pistol. The Rapier rider is the trick: a hit grants Advantage on the next attack before the end of the turn, so the order is Rapier first, then Rapier at Advantage, then Pistol at Advantage if the second Rapier landed. With +7 to hit and 13 piercing on the rapier plus 15 on the pistol, the captain can put 41 average on a single PC in one turn. The optimized opener at range is three Pistol shots if the captain has the ammunition.

Captain's Charm is the bonus action. DC 14 Wisdom save or Charmed until the start of the captain's next turn. Use it on the party's biggest hitter the round before the captain wants to disengage, or on the healer to deny a clutch heal. A Charmed paladin watches their cleric die and does nothing.

Riposte is the reaction. When the captain is hit by a melee attack, they add 3 to their AC against that attack and, on a miss, get a free Rapier strike. AC 17 plus 3 is AC 20, which turns most low-end melee attacks into misses. Save Riposte for the fighter's biggest swing, not the rogue's first try.

The captain retreats at 30 HP. They have a ship to sail and a crew waiting for orders. Have them slash a rope, drop into a longboat, and salute the party as they row out of range.