Pirate

A pirate ally is hired muscle, a deserter, a roguish romantic interest, or a contracted partner for one specific job. The framing the party will accept is contract: the pirate is here for a cut, and once the cut is paid she's gone. Establish the cut up front, in coin or in something the pirate names (a captured ship, a particular relic, passage to a port the party has already secured).

In combat, the pirate is a flanker. Two Daggers at +5 plus Enthralling Panache makes her a useful debuffer in any melee that includes named enemies, because Charmed buys the party's barbarian a free round against an enemy lieutenant. Range 20/60 means she also threatens from second-line position behind the party's tank. She will not stand in the front rank and she will not tank a fireball. She picks her shots, takes credit for the kill, and asks about loot during the encounter.

Out of combat, the pirate is a problem with charm. Charisma 14 and the saved-vs-Wisdom Charm imply a sociable predator; she'll flirt with the bartender, lift a purse from the merchant, and pick a fight with anyone who calls her on either. Don't try to make her a moral character. The party hired her to do pirate things, and she will do them in the inn.

When the contract ends, she vanishes that night. If the party paid fairly, she might come back next season with a tip about a galleon worth boarding. If the party stiffed her, the next pirate they meet already knows their faces.

A pirate is a charismatic skirmisher with knives. CR 1, 33 HP, AC 14, two Dagger attacks at +5 for 1d4+3 piercing, and a Charm rider tucked into Multiattack via Enthralling Panache. One pirate is a tavern brawl; six pirates plus a captain is a deck-fight. The encounter design that earns the stat block is the deck-fight, because Enthralling Panache rewards numbers.

Open with daggers thrown. Daggers have a 20/60 ft. range, so the pirate can plink from the rigging or from across the gangway turn one without losing initiative tempo. Once the party closes, switch to melee Daggers and start using Enthralling Panache. Multiattack lets the pirate replace one Dagger with a use of Enthralling Panache: DC 12 Wisdom save or Charmed until the start of the pirate's next turn. Run multiple pirates and stagger the saves; one Charmed PC can't attack the pirate who Charmed her, which means the cleric is stuck while a second pirate stabs her.

Target priority depends on what the pirates are after. If they want loot, they go for the lightly armored merchant or the wizard with the bag of holding and try to grab and run. If they want hostages, the captain calls for one specific PC by name (the noble, the heir, the one who matters to the plot), and the rest of the boarding party tries to drag that PC back to the longboat. If the party is just in the way, the pirates fight a cover-and-knife retreat back to their own ship, throwing daggers from the rail as they cast off.

Pirates break when the captain falls or the pay stops. Morale is the encounter's off switch. Drop the captain and the rest scatter overboard, hands up, or to the masts. Have one survivor offer to talk in exchange for not hanging. The talk is the next adventure hook.