Medium Humanoid (High-Elf), Neutral Evil
AC 23 Elven Chainmail +3    Initiative +12 (22)
HP 536 (29d20 + 232)
Speed
Mod Save
STR 28 +9 +17
DEX 18 +4 +4
CON 20 +5 +13
Mod Save
INT 27 +8 +16
WIS 18 +4 +4
CHA 18 +4 +4
Skills Athletics +25, Deception +20, Insight +12, Perception +25, Sleight of Hand +12, Stealth +12
Resistances Psychic; Bludgeoning, Piercing, and Slashing from Nonmagical Attacks
Immunities Fire; Charmed
Gear Elven Chain +3, Kinsbane, Seraphina's Cuff, Antimatter Revolver, Ring of Spell Storing, Ring of Freedom of Movement, Antimagic Loadstone Shards,
Senses Blindsight 15ft., Darkvision 60ft.; Passive Perception 35
Languages Celestial, Common, Common Sign Language, Elvish, Infernal, Sylvan, Thieves' Cant
CR 26 (XP 90,000, or 155,000 in lair; PB +8)
Traits

Kinsbane the Bloody Blade.  This magical greatsword is the last thing Captain Rook has from his home. He carries it as both a weapon and a reminder of what he did for his daughter, and why he fights for her forgiveness. The chips and scars on the blade drag across the skin on a hit.

Bleed: When a target takes damage from Kinsbane, the target must made a DC 20 DEX saving throw or take the damage received again at the start of their next turn (included in weapon attack). If the target receives any healing before the start of their next turn the damage is halved. If the healing brings the target up to full health, they do not take the bleed damage at the start of their turn.

Ring of Freedom of Movement.  While attuned, Captain Rook ignores difficult terrain, and magical effects can't reduce its speed or cause it to be restrained. It can spend 5 feet of movement to escape from nonmagical restraints or being grappled.

Great Weapon Master. Captain Rook has learned to put the weight of a weapon to his advantage, letting its momentum empower his strikes. You gain the following benefits:  On his turn, when he score a critical hit with a melee weapon or reduce a creature to 0 hit points with one, he can make one melee weapon attack as a bonus action.

Before he makes a melee attack with Kinsbane, he can choose to take a -5 penalty to the attack roll. If the attack hits, he adds +10 to the attack's damage.

Combat Action. A Combat Action begins at the end of Captain Rooks Turn. As rook raises his sword in a defensive measure, he begins to track all enemies within 30ft of himself. At the start of his next turn, the combat action triggers. The combat action, automatically hits and delivers damage to all targets within range.

Action Surge (2/day). On your turn, you can take one additional action on top of your regular action and a possible bonus action.

Once you use this feature, you must finish a short or long rest before you can use it again.

Actions

Multiattack. Captain Rook makes 4 attacks with Kinsbane and/or the Antimatter Revolver, or one of the option listed below:

- 1 attack with Kinsbane and drink 1 potion.
- 1 attack with Kinsbane and uses Seraphina's cuff

Kinsbane (Greatsword). Melee Weapon Attack: +9 to hit, reach 10ft., one target. Hit: 23 (2d6+17) slashing damage. Bleed When a creature is hit by Kinsbane, they must make a DC 20 DEX save or take the same slashing damage from bleeding at the start of their next turn.

Graze. If his attack roll with this weapon misses a creature, he can deal damage to that creature equal to the ability modifier you used to make the attack roll. This damage is the same type dealt by the weapon, and the damage can be increased only by increasing the ability modifier. Graze does not cause the Bleed effect.

Seraphina's Cuff (Magic Guantlet) (3 Charges). This gold and silver carved cuff around Captain Rooks Right wrist is the last possession he was gifted from his late lover. Seraphina gifted it to him with the inscription "I will never Let Go." The magic has since warped with the blood spilled by Captain Rook.

Captain Rook has the ability to cast the Hold Person spell (listed below). The amount of charges used determines the spells level.
Choose a humanoid that you can see within range. The target must succeed on a DC 24 Wisdom saving throw or be paralyzed for the duration. Seraphina's Cuff takes over the Concentration on the spell from Captain Rook. At the end of each of its turns, the target can make another Wisdom saving throw. On a success, the spell ends on the target.

Antimatter Revolver. Ranged Weapon Attack: +12 to hit, range 40/120 ft., one target. Hit: 12 (2d8+4) necrotic damage.

Sap. If you hit a creature with this weapon, that creature has Disadvantage on its next attack roll before the start of your next turn.
Limited Ammunition The Antimatter Revolver has 6 shots before it needs to be reloaded. Captain Rook can reload as a bonus action.

Combat Action - Steel Wind Strike. Captain Rook draws and flourishes his dagger, and then vanishes to strike like the wind. Choose up to five creatures you can see within range. The target takes 6d10 force damage without the bleed Ability.

Captain Rook can then teleport to an unoccupied space you can see within 5 feet of one of the targets you hit or missed.

Combat Action - Scorched Earth. Captain Rook's fury begins to burn around the base of his stance. The ground begins to heat and burn.

At the start of his next turn, the area around Captain Rook Each creature in a 20-foot-radius sphere centered on Himself must make a Dexterity saving throw. A target takes 8d6 fire damage, and on a failed save takes the same fire damage again at the start of their next turn unless the flames are put out using an action. The fire spreads around corners. It ignites flammable objects in the area that aren’t being worn or carried.
Combat Action - Harrowing Bloodlust. Captain Rook's bloodlust is palpable. As he braces for oncoming attacks, creatures within 60ft. begin to feel a terrifying presence flood over them. All creatures within 60ft. of Captain Rook automatically gain the Frightened condition. Each enemy must make a DC 20 WIS save, or also gain the Paralyzed as they are paralyzed by fear. 
Bonus Actions

Second Wind (4/Rest). Captain Rook has a limited well of stamina that he can draw on to protect himself from harm. On his turn, he can use a bonus action to regain hit points equal to 1d10 + 26.

Pommel Strike (2/Rest). Captain Rook Makes a Melee Attack against an enemy within range with the pommel of Kinsbane (Use Kinsbane attack for to hit stats). On a hit, the creature takes 17 bludgeoning damage and must make a DC 20 CON save or become Dazed until the end of his next turn.

Great Weapon Master. On your turn, when Captain Rook scores a critical hit with a melee weapon or reduce a creature to 0 hit points with one, he can make one melee weapon attack as a bonus action.

Reactions

Parry. Captain Rook adds +4 to his AC against one melee attack that would hit it. To do so, Captain Rook must see the attacker and be wielding a melee weapon.

Silvery Barbs (2/day, Ring of Spell Storing). You magically distract the triggering creature and turn its momentary uncertainty into encouragement for another creature. The triggering creature must reroll the d20 and use the lower roll.

You can then choose a different creature you can see within range (you can choose yourself). The chosen creature has advantage on the next attack roll, ability check, or saving throw it makes within 1 minute. A creature can be empowered by only one use of this spell at a time.
Counterspell (1/day, Ring of Spell Storing). Captain Rook attempts to interrupt a creature in the process of casting a spell. If the creature is casting a spell of 3rd level or lower, its spell fails and has no effect. If it is casting a spell of 4th level or higher, Captain Rook makes an ability check using his intelligence ability at disadvantage. The DC equals 10 + the spell's level. On a success, the creature's spell fails and has no effect.
Legendary Actions
Captain Alaric Rook can take 3 legendary actions (4 aboard the Red Stallion), choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature's turn. Captain Rook regains spent legendary actions at the start of its turn.
Bloodlust (costs 1 action). Captain Rook can grant himself advantage on all attack's and saving throws against 1 creature until the end of his next turn. He also gains the ability to make one attack with Kinsbane as a bonus action.
Rally Crew (costs 1 action). Captain Rook rallies the spirits of all nearby Golden Tongue crew. Whether its from inspiration or fear, that's unknown.
All Golden Tongue crew members and allies within 120ft that can hear him gain 30 temporary hit points. If this Legendary action is used more than once during a combat, reduce the number of Rallied Allies by 1d4+1 each time used.
Coordinate Attack (costs 2 actions). Captain Rook's centuries of being Pirate Lord of the Golden Tongues has lead him and his crew to work in expert timing.
Captain Rook can command up to 5 Golden Tongue Crew to take one of the following actions utilizing their reaction.

- Disarm Enemy: Each Crew member that can makes a melee disarming strike attack against an enemy. The enemy must succeed on a DC [8+STR+Profiency], or be disarmed.
- Grapple and Guard: Each Crew Member moves to Guard Captain Rook. Using the Grapple Action, up to all crew members grab Captain Rook, moving him up to 30ft without provoking Opportunity Attacks. Alternatively, each crew member can attempt to make a grapple check against an enemy within 30ft of Captain Rook. On a success, Captain Rook can move up to half his speed away without provoking Opportunity Attacks from creatures within melee range of Captain Rook.
- Volley: Each crew member makes a ranged weapon or spell attack at advantage, directed at one creature.
Mythic Actions

Mythic Action Name. Enter the description for how mythic actions work for your monster here.

Mythic Action Name (Costs # Actions). Enter the description for your mythic action.

Description

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Lair and Lair Actions

Captain Alaric Rook has captained The Red Stallion for hundreds of years. Over the years he has developed a strange relationship with the ships soul Lenor; she is one of the few in the universe that he regards with kindness. The daughter of the craftsman of The Red Stallion, Lenor was fascinated by the ships bright red timber, overwhelming scale and masthead dedicated to her favorite horse. On the flagship sailing however, they were attacked by wayward pirates. Lenor along with everyone else was killed and their bodies dumped into the void of the astral sea. Lenor's soul however bound to the ship, forever locking her in the floating red prison full of memories of her lost loved ones. Her soul is tied to the masthead. If destroyed, there is a 75% chance Lenor passes on, and a 25% chance she is trapped to the remains of the ship. 

This lair includes the area in the air envelope around The Red Stallion, area up to 50ft surrounding the docks, and anywhere in The Pirate Lords Lair. 

Lair Actions

On initiative count # (losing initiative ties), the [monster name] takes a lair action to cause one of the following effects; the [monster name] can’t use the same effect two rounds in a row:

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Regional Effects

The region containing a legendary [monster name]’s lair is [enter the effect description], which creates one or more of the following effects:

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If the [monster name] dies, these effects fade over the course of #d# days.

SketchyWolfster