Captain Halbren "Silver Tooth" Reeve

Lightfooted. Captain Silver Tooth can take the Dash or Disengage action as a bonus action on each of his turns.

Suave Defense. While Captain Silver Tooth is wearing light or no armor and wielding no shield, his AC includes his Charisma modifier.

Curse of the Deep. Upon the death of the crew and captain, Captain Silver Tooth rises again at the end of the round, taking his initial initiative roll. When he does so he is counted as undead for the remainder of the time, or 1d4 days later when he regains his physical form. Upon a second death, he is banished to the water elemental plane until 2d4 days later where he comes back again in his original forms. The only way to break this curse is to cast dispel curse on the figurehead of the ship.

Hade's Revenge. Upon the second death of Captain Silver Tooth, the sea whispers a singular chant as the water around the sinking Hades Deceit turns a dark green. With the entire death of crew and captain, the chanting thunders before becoming silent and the Kraken erupts from the depths. 

Multiattack. Captain Silver Tooth makes three attacks: one with his dagger and two with his rapier.

Dagger. Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4 + 5) piercing damage.

Rapier. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 9 (1d8 + 5) piercing damage. 

Captain Silver Tooth can take 3 legendary actions, 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 Silver Tooth regains spent legendary actions at the start of his turn. 

Weapon Attack. Captain Silver Tooth makes a weapon attack.

Command Ally.  Captain Silver Tooth targets one ally it can see within 30 feet of it. If the target can see and hear Captain Silver Tooth, the target can make one weapon attack as a reaction and gains advantage on the attack roll. 

Charm Foe (Costs 2 Actions). Captain Silver Tooth targets one enemy it can see within 30 feet of it. If the target can see and hear him, the target must succeed on a DC 16 Wisdom saving throw or become charmed until Captain Silver Tooth's next turn or until it takes damage from Captain Silver Tooth or one of his allies.