Capitán Barbarrara

Captain $Weirdbeard$ is an extraordinary Illithid.

Commanding a crew of fearsome pirates, he sails the seas with a steady tentacle. He captures slaves for the colony of Illithids he comes from, making many of them minions brainwashed to serve him and the Elder Brain he keeps hidden on an Island.
Legend says he was a normal Illithid colony, until psionic hunger came.
When the Illithid empire fell, and after years of hunger and isolation from any psionic sustain, the Elder Brain turned mad and made a desperate pact with an Old One: $Chuthullu$, The Deep One. In exchange, $He$ provided the Elder Brain with a pirate ship full of buccaneers, that found themselves on the island after a storm. Slowly turned mad even before they could repair the ship, as the forces of The Deep One and an Elder Brain in coalition were too much resist.
They serve the Elder Brain now, accumulating enough arcane power to one day set Chuthullu free. That Day the Elder Brain and Chuthullu will become one, and reach over this land, and all Illithids will feel the awakening of a new master, worse than any Elder Brain ever before.

Weirdbeard raised as the most capable fighter and resilient Illithid, not only going through the transformation painlessly but also keeping all his sailing abilities and some more. His communion with The Old One also provides him with supernatural abilities and powers, and a ship that carries as many curses as cannons. His devotion to the Deep One is as strong as his loyalty to the Elder Brain, but he may enjoy his freedom and cruelty a bit too much to be trusted.

Cpt. Weirdbeard

Medium Humanoid (Illithid), Chaotic Evil

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• Armor Class 15 (studded leather)
• Hit Points 111 (13d8 + 14)
• Speed 30 ft.

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STR	DEX	CON	INT	WIS	CHA
16	14	14	19	17	17
(+3)	(+2)	(+2)	(+4)	(+3)	(+3)

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• Saving Throws Int +7, Wis +6, Cha +6
• Skills Arcana +7, Deception +6, Insight +6, Perception +6, Persuasion +6, Stealth +4, Athletics +5, Intimidation +4
• Senses darkvision 120 ft., passive Perception 16
• Languages Common, Deep Speech, Undercommon, telepathy 120 ft.
• Challenge 9 (5,000 XP)
• Proficiency Bonus +3

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Magic Resistance. The mind flayer has advantage on saving throws against spells and other magical effects.

Flourish. The captain adds its Charisma modifier to the damage roll for its longsword attacks (included in the attack).

Sea Legs. The captain has advantage on ability checks and saving throws to resist being knocked prone.

Spellcasting. The Captain is a 4th-level spellcaster. Its spellcasting ability is Charisma (spell save DC 13, +5 to hit with spell attacks). It has the following warlock spells prepared:

Cantrips (at will): friends, mage hand, prestidigitation, ray of frost
1st level (4 slots): Hex, fog cloud, Arms of Hadar, witch bolt
2nd level (3 slots): gust of wind, Crown Of Madness, misty step

Innate Spellcasting (Psionics). The Captain's innate spellcasting ability is Intelligence (spell save DC 15). It can innately cast the following spells, requiring no components:

At will: detect thoughts, levitate
1/day each: dominate monster, plane shift (self only)

Magic Resistance. The Captain has advantage on saving throws against spells and other magical effects.

Spellcasting. The Captain is a 10th-level spellcaster. Its spellcasting ability is Intelligence (save DC 15, +7 to hit with spell attacks). The Captain has the following wizard spells prepared:

Cantrips (at will): Eldritch blast, blade ward, dancing lights, mage hand, shocking grasp
1st level (4 slots): detect magic, disguise self, shield, sleep
2nd level (3 slots): blur, invisibility, ray of enfeeblement
3rd level (3 slots): clairvoyance, lightning bolt, sending
4th level (3 slots): confusion, hallucinatory terrain
5th level (2 slots): telekinesis, wall of force

Actions

Multiattack. The captain makes two attacks: one with its hand crossbow and one with its longsword.

Tentacles. Melee Weapon Attack: +7 to hit, reach 5 ft., one creature. Hit: 15 (2d10 + 4) psychic damage. If the target is Medium or smaller, it is grappled (escape DC 15) and must succeed on a DC 15 Intelligence saving throw or be stunned until this grapple ends.

Longsword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 9 (1d8 + 5) slashing damage, or 10 (1d10 + 5) slashing damage if used with two hands.

Ship Invisibility (Recharges after a Short or Long Rest). A ship upon which the captain stands, along with all creatures and objects aboard it, becomes invisible to creatures not aboard the ship. The captain must concentrate on this magical effect to maintain it (as if concentrating on a spell), and it lasts for up to 1 hour. The effect ends if the captain leaves the ship.

Extract Brain. Melee Weapon Attack: +7 to hit, reach 5 ft., one incapacitated humanoid grappled by the Captain. Hit: The target takes 55 (10d10) piercing damage. If this damage reduces the target to 0 hit points, the Captain kills the target by extracting and devouring its brain.

Mind Blast (Recharge 5–6). The Captain magically emits psychic energy in a 60-foot cone. Each creature in that area must succeed on a DC 15 Intelligence saving throw or take 22 (4d8 + 4) psychic damage and be stunned for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

Reactions

Shape Up, Ye Dog (2/Day). Whenever a friendly creature within 30 feet of the captain that can hear it misses with an attack, the captain can yell perilous threats to allow that creature to reroll the attack roll.

Legendary Actions

As a reaction to receiving damage the Captain can quickly counterattack. Longsword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 9 (1d8 + 5) slashing damage, or 10 (1d10 + 5) slashing damage if used with two hands.

Eldritch blast Ranged Magic Attack +3 to hit, 120 feet, one target. Hit : (1d10 +3) force damage.

He commands a group formed of already transformed Illithid and humanoid pirates, some of them crazy cultist, warlock-like humanoids, creatures of the deep, deep one followers, horrors from the seas and floating brains that move around like terrifying jellyfish.