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Freebooting Gambler

Medium humanoid (elf), neutral

Armor Class 16 (studded leather)
Hit Points 66 (12d8 + 12)
Speed 30 ft.

12 (+1) 18 (+4) 12 (+1) 10 (+0) 14 (+2) 14 (+2)

Saving Throws Dexterity+6
Tools forgery kit
Skills Deception +6, Insight, +4, Sleight of hand +6
Senses darkvision 60 ft., passive Perception 12
Languages Common, Elvish
Challenge 2 (450 XP)

Special Traits

  • Bad reputation. The freebooting gambler has disadvantage on any Charisma check involving interaction with reputable people aware of its kind.
  • Bluff. The freebooting gambler adds twice its proficiency bonus (+4) to all Charisma (deception) checks (included above) Fey Ancestry. The freebooting gambler has advantage on saving throws against being charmed and can’t be magically put to sleep.
  • Lucky (3/day). The freebooting gambler rolls a 1 on an attack, ability check or saving throw, it can reroll but must take the new result.
  • Sneak Attack. Once per turn, the freebooting gambler 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 freebooting gambler that isn’t incapacitated and the freebooting gambler doesn’t have disadvantage on the attack roll.
  • Special Gear. Dice set (loaded and normal), playing card set, potion of healing, 54 gp.


  • Multiattack. The freebooting gambler makes two attacks: two with its longsword, or two with its crossbow.
  • Longsword. Melee Weapon Attack: +3 to hit, reach 5 ft., one target. Hit: 7 (1d8+1) slashing damage.
  • Longbow. Ranged Weapon Attack: +4 to hit, reach 5 ft. or range 150/600 ft., one target. Hit: 5 (1d4 + 2) piercing damage.


This vagabond sailor lives by its wits and its luck and rarely remains with any crew for the long haul, preferring to skip from vessel to vessel and port to port always in search of the next big score or run of luck (or perhaps fleeing a deal or a game gone bad).

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.