Sly the Shady

Small humanoid (goblinoid), Commander, neutral evil

Armor Class

18 (studded leather)

Hit Points

157 (35d6+35)

Speed

30 ft.

Saving Throws

Dex +14

Skills

Perception +9, Persuasion +7, Sleight of Hand +14, Stealth +14

Damage Resistances

poison

Senses

darkvision 120 ft., blindsight 60 ft., passive Perception 19

Languages

Common, Goblin, Thieves’ Cant

Challenge

9 (5,000 XP)

Proficiency Bonus

+4

Nimble Escape. Sly the Shady can take the Disengage or Hide action as a bonus action on each of their turns.

Sneaky. Sly the Shady can try to hide when they are lightly obscured from the creature from which they are hiding.

Hidden Attack. If Sly has advantage on a melee attack roll against a target, or if another Goblin Thief is adjacent to a target Sly is making a melee attack against, Sly deals an extra 5 (1d10) piercing damage on the hit and steals 4d4 gold from the attack.

Distraction… With a Dagger. When Sly hits a creature with a melee weapon attack, they can use their bonus action to steal make a Sleight of Hand check against the target’s passive Perception, stealing 10d4 gold from them on a success. If a target has no gold or runs out, Sly will target a different creature.

Get ‘Em, Crew. If there are two or more Goblin Thieves adjacent to a creature and within 60 feet of Sly, those thieves always steal the maximum amount of gold when using Distraction… With a Dagger.

Cool Cat’s Cowl. Sly the Shady wears the Cool Cat’s Cowl.

Actions

Multiattack. Sly makes two attacks with their slithering armblade and can use either Smoke If Ya’ Got ‘Em or Mugged.

Slithering Armblade. Melee Weapon Attack: +10 to hit, reach 5ft., one target. Hit: 7 (1d4+6) piercing damage plus 9 (2d8) poison damage.

Goblin Hand Crossbow. Ranged Weapon Attack: +10 to hit, range 30/90 ft., one target. Hit: 9 (2d2+6) piercing damage plus 2 (1d4) poison damage.

Smoke If Ya’ Got ‘Em (2/Day). Sly flicks the lit cigar they have hanging from their mouth at a target within 20 feet. All Goblin Thieves within 90 feet may use their reaction to make a ranged weapon attack against that target, switching to their ranged weapon as part of the reaction.

Mugged. Sly punches an adjacent target. That target loses 10d4 gold and must choose between the following:

– Take 11 (2d10) bludgeoning damage.

– Make a DC 15 Constitution saving throw or be stunned until the end of their next turn.

– Make a DC 18 Dexterity saving throw or be blinded until the end of their next turn.

Reactions

Smoke Activated Goblin (3/Day). When Sly the Shady is the target of a melee weapon attack, they can drop a flask of smoke. A cloudy substance fills a 10-foot-radius sphere centered on Sly, making the area heavily obscured for 1 round.