Pirate Boatswain

Medium humanoid (human), neutral evil

Armor Class 14 (studded leather)
Hit Points 104 (16d8 + 32)
Speed 30 ft.

STR	DEX	CON	INT	WIS	CHA
12 (+1)	17 (+3)	14 (+2)	10 (+0)	11 (+1)	10 (+0)

Saving Throws Dexterity+5
Tools Thieves’ tools
Skills Perception +3
Senses passive Perception 13
Languages Common
Challenge 3 (700 XP)

Special Traits

• Sneak Attack. Once per turn, the boatswain deals an extra 7 (2d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the boatswain that isn’t incapacitated and the boatswain doesn’t have disadvantage on the attack roll.

Actions

• Multiattack. The boatswain makes two attacks with its shortsword, or two attacks with its heavy crossbow.
• Short sword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 6 (1d6 + 3) slashing damage.
• Heavy crossbow. Ranged Weapon Attack: +5 to hit, reach 5 ft. or range 100/400 ft., one target. Hit: 5 (1d10 + 2) piercing damage.

About

A few of these scurvy scalawags might command a small sloop or shoreward press gang of their own, but more often they serve as veteran hands before the mast, keeping the decks orderly and well-maintained and knocking any newly shanghaied swabbies into shape.