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The Red Skeleton Captain
Large undead, lawful evil
Damage Vulnerabilities Radiant, Acid
Boss Fight. At the start of combat, the creature rolls twice for initiative, taking two turns per round of combat. At the start of each round, the creature must reroll for initiative once and replace one of its turns with the new result.
Big Boss Upon starting a battle all other skeletons and pirates within a 100ft radius will move to join the fight.
Under Your Skin When fighting a human roll 1d4 extra die for each damage roll
Taunt. Once on its turn, the skeletal pirate can use an action taunt a creature within 60 feet of it which can see or hear it. The creature must make a DC 13 Wisdom saving throw. On a failure, the creature is taunted by the skeletal pirate until the end of its next turn.
Undead Fortitude. If damage reduces the skeleton pirate to 0 hit points, it must make a Strength saving throw with a DC equal to half the damage taken, unless the damage is radiant or from a critical hit. On a success, the skeleton pirate drops to 1 hit point instead.
Multiattack. The skeleton pirate boss can use its 1000-Yard Stare. It then makes two attacks.
Cutlass is Cut-more Melee Weapon Attack: +20 to hit, reach 5 ft., one target. Hit: 60 (6d10 + 10) Slashing
Flintlock Pistol. Ranged Weapon Attack: +5 to hit, range 20/60, one target. Hit: 8 (1d10 + 3) piercing damage.
1000-Yard Stare' The two holes which used to contain eyes match gaze with a single target and paralyze them with fear for 1 turn. Targets must make DC constitution roll of 13 to escape the gaze (can be a bonus action).
The boss can take 1 boss action, choosing from the options below. Only one boss action option can be used at a time and only at the end of another creature's turn. The boss regains its spent boss action at the start of the round.
(Optional) Attack. The creature may move 10 feet and make a single weapon attack
(Optional) Summon. The creature summons a number of appropriate creatures. This action can be performed twice, and a third time when Bloodied Resistance activates.
(Optional) Cast Spell. The creature casts a spell it knows. This action can be performed twice, and a third time when Bloodied Resistance activates.
A creature with the Boss Template applied to it.