Pirate Captain

Medium humanoid (any race), any non-lawful

Armor Class 15 (studded leather)

Hit Points 65 10d8+20

Speed 30ft

STR

15 +2

DEX

16 +3

CON

14 +2

INT

14 +2

WIS

11 0

CHA

14 +2

Saving Throws Str +4, Dex +5, Wis +2

Skills Athletics +4, Deception +4

Languages any two languages.

Challenge 2 (450 XP)

Actions

Multiattack. The captain makes three melee attacks; two with its scimitar and one with its dagger. OR the captain makes two ranged attacks with daggers.
Scimitar. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 6 1d6+3 slashing damage.
Dagger. Melee or Ranged Weapon Attack: +5 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 5 1d4+3 slashing damage.

Reactions

Parry. The captain adds 2 to its AC against one melee attack that would hit it. To do so, the captain must see the attacker and be wielding a melee weapon.

It takes a strong personality, ruthless cunning, and a silver tongue to keep a gang of bandits in line. The pirate captain has these qualities in spades.
In addition to managing a crew of selfish malcontents, the pirate captain has a ship to protect and command. More than treasure, a pirate captain craves infamy. A prisoner who appeals to the captain's vanity or ego is more likely to be treated fairly than a prisoner who does not or claims not to know anything of the captain's colorful reputation.