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Pirate Boatswain

Medium humanoid (human), neutral evil

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

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.


  • 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.


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.

Section 15: Copyright Notice

Pirate Campaign Compendium © 2018, Legendary Games; Lead Designer Jason Nelson. Authors: Alex Augunas, Jeff Gomez, Matt Goodall, Jim Groves, Tim Hitchcock, Victoria Jaczko, Jonathan H. Keith, Lyz Liddell, Thomas J. Phillips, Alistair J. Rigg, Alex Riggs, Loren Sieg, Neil Spicer, Todd Stewart, Rachel Ventura, Michael D. Welham, Linda Zayas-Palmer.