Skeleton Corsair

Basic pirate, nothing special

 - Has a small chance to Drop its Bandana

Drowned Pirate

Basic pirate that spawns in every single ship

 - Has a small chance to Drop its Hat

 - Applies Deadly Seas effect 

Drowned Captain

Spawns only in his personal ship. 

 - Drops a logbook full of maps, and has a small chance to drop a Captain's Feather

 - Summons Drowned Pirates

 - Applies Deadly Seas effect 

 Key Keeper

 Can be seen guarding Treasure Chests and Drops the Treasure Key to open said chest

 - Has a small chance Drop its Bandana or the Anchor on its back 

 - Sits and waits before attacking

 - Gets angry when hit

 - Sinks in water

Bouldering Marauder

Spawns on medium and onward ships

 - High knockback

 - (Almost) Immune to knockback

 - Applies Weakness 

Lobber Buccaneer

Spawns most often in the crow's nests of ships

 - Has a small chance to Drop its Hat

 - Shots rotten flesh laced with Deadly Seas

 - Spawns four Poisoned Rotten Fleshes over his head when defeated

Golden Skeleton

Rare skeleton with healing properties that only spawns in the Drowned Captain's Ship

 - Scared of Pirates

 - Drops His Head

Cast Away Skeleton

Shipwrecked skeleton that has a small chance to spawn on beaches

 - Has a small chance to spawn holding a Shell Dagger

 - Has a small chance to drop said Shell Dagger

 - Has multiple variations with differing Speeds and Health 

Drowned Corsair

Basic Pirate, is found wandering around in beaches

 - Has a small chance to Drop its Bandana

 - Applies Deadly Seas effect

Ghost Creeper 

Spawns around the masts of ships, being able to fly around and attack unsuspecting players

 - Spawns a small floating TNT when defeated that explodes once it hits the ground

 - Has a high chance of dropping Gem Shards and a small chance to drop Ectoplasm when killed

Sander

Small sand creature that hunts in packs, spawning in beaches

 - Hits surprisingly hard

 - Hunts cows

 - Can be given Raw Beef or Steak in trade for blocks of Sand

Dusty Skeleton

Simple minion of the Treasure Pillar

- Spawns its head when defeated, that if not destroyed in time will respawn into a new Dusty Skeleton

- Can Spawn with a Shell Dagger

Lost Captain

Boss of the Treasure Pillar, has many tricks that it will use against anyone trying to steal his treasure

 - Drops a Pocket-Sized Sand Typhoon and has a smal chance to drop a Lost Captain's Feather

 - Applies Weakness and Deadly Seas

 - Spawns Sand Tornadoes during the fight

 - Blinds attacker from time to time

Wither Skeleton Captain

Can be Summoned through a Special Horn (Subject to Change Soon) 

 - Drops a Cursed Medallion, has a small chance of dropping a Wither Falchion and a Wither Captain's Feather

 - Applies Curse of Armor Breaching

 - Fires Wither Skulls periodically during the fight

 - Leaves behind a Parrot when defeated

Skeleton Captain

Spawns on Sleeping on his own personal shipwreck in Frozen Ocean Biomes

 - Drops Fang Talismans, has a small chance of dropping a Golden Scimitar and Skeleton Captain's Feathers

 - Attacks with evoker fangs

 - Applies Deadly seas effect

(From Top Left to Bottom Right)

Golden Skull

Removes all Potion Effects and Grants Regenaration when Right-Clicked 

Drops from Golden Skeleton

Aquamarine Skull

Applies conduit power when held in water

Found in Treasure chests

Skull of Doom

Can One-Shot (almost) any Mob with a Left-Click, breaking it in the process

Extremely Rarely found in Treasure chests

Dragons Eye Gem

Provides a constant effect of Health Boost when in a players Inventory

Rarely found in Treasure Chests

Flame Artifact

Shoots 3 Explosive Fireballs or Rapid Fires normal Fireballs in the direction the player is looking When Right-Clicked. Switchs between Fire Modes with a Left-Click

Found in Treasure Chests

Fang Talisman

Summons Evoker Fangs all around the player when Right-Clicked

Dropped by the Skeleton Captain

Cursed Medallion

Grants Great Strength when Held-Right-Clicked, Has 3 UsesDropped by the Wither Skeleton Captain

Pocket-sized Sand Typhoon

Launches the player into the Air when Right-Clicked

Dropped by the Lost Captain

Cursed Die

Rolls a number between 1-6 when Right-Clicked, Results will Vary 

Rarely found in Treasure Chests

Magic Map

Gives a Map leading to a Rare Pirate Structure when Right-Clicked

Rarely found in Treasure Chests

Upgrade Template of The Seas

Used in crafting Rare Items in a Smithing Table

Can be Crafted from 3 Broken Templates and 1 Gem Shard

Broken Template of the Seas

Used to craft the Upgrade Template of the Seas 

Always dropped by any Captain Enemy

Trapped Sander

Right-Click to Release the trapped critter

Can be found in many different structures

Withered Cursed Horn (Subject to Change Soon)

Used Spawn the Wither Skeleton Captain during Thunderstorms

Rarely found in Treasure Chests

Skull Scythe Blade

Used to craft the Skull Scythe

Very Rarely found in Treasure chests

Skull Blade

Used to craft the Skull Crusher

Very Rarely found in Treasure chests

Skull Handle

Used to craft both of the Skull weapons,

Very Rarely found in Treasure chests

Skull Axe Head

Used to craft the Skull Shatterer

Very Rarely found in Treasure chests

(From Top Left to Bottom Right)

Corsair Bandana

Simple, not so reliable bandana

Rarely Dropped by Drowned Corsairs

Pirate Bandana

Simple, reliable bandana

Rarely Dropped by Skeleton Corsairs

Bandana of Rage

Provides Strength 1 while worn

Rarely Dropped by Key Keepers

Swashbuckler Hat

Simple, striking design

Rarely Found in Loot Chests (Subject to Change)

Buccaneer hat

Simple, unique design

Rarely dropped by Lobber Bucaneers

Pirate Hat

The classic

Rarely dropped by Drowned Pirates

Diamond Pirate Hat

The classic (But Better!)

Crafted in a Smithing Table

Netherite Pirate Hat

The classic [(But Better!)^2]

Crafted in a Smithing Table

Captain's Hat

Grants Resistence 1 while at Sea

Craftable  with a Captain's Feather

Lost Captain's Hat

Grants Immunity to Blindness, Weakness and Levitation Effects

Craftable with a Lost Captain's Feather

Wither Skeleton Captain's Hat

Grants Immunity Wither Effect and Fire Damage

Craftable with a Wither Skeleton Captain's Feather

Skeleton Captain's Hat

Better Than a Netherite Helmet, does nothing else (Subject to Change)

Craftable with Skeleton Captain's Feathers

Luxurious Captain's Hat

Very Stylish, counts as Gold Armor when around Piglins

Rarely Found in Treasure chests

Lucky Pirate Hat

Grants Luck 1, counts as Gold Armour when around Piglins

Rare Reward from Cursed Die

Crowns of the Seas

Does apparently nothing, though it exudes a Menacing Aura, counts as Gold Armor when around Piglins

Rarely Found in Treasure chests

(From Top Left to Bottom Right)

Iron Cutlass

Classic Pirate Sword, with a very Fast Attack Speed

Found in Ship Chests

Diamond Cutlass

Classic Pirate Sword but Better

Crafted in a Smithing Table

Netherite Cutlass

Classic Pirate Sword but Better, Better!

Crafted in a Smithing Table

Scimitar

Deals Extra Damage to enemies with No Armour

Found in ship chests

Shell Dagger

Grants Strength 1 when Held in Water/Rain

Drops rarely from certain mobs

Double Edge Sword

Throws mobs Upward with each strike

Found in Treasure chests

Gem Blade

Consumes Gem Shards to deal Extra Damage

Can be crafted

Cused Anchor

Grants Curse of Sinking both to the player holding and to enemies hit

Drops rarely from Key Keeper

Phantom Blade

Launches the player Foward when Right-Clicked

Found in Treasure chests

Gilded Shovel

Faster then gold tools, small chance to Drop Gold Nuggets when used, does a High Amount of Knockback

Found in Treasure chests

Gilded Pickaxe

Faster then gold tools, small chance to Drop Gold Nuggets when used, does a High Amount of Knockback

Found in Treasure chests

Golden Scimitar

Deals Extra Damage to enemies With Armor and Spawns Evoker Fangs every 10th Hit

Drops rarely from the Skeleton Captain

Midas Sword

Grants Greed Effect to the player, Greed Greatly Increases Damage but requires a constant Supply of Gold, if said gold runs out, the effect will start Damaging the Player

Found in Treasure chests

Sander Annihilator

Explodes Sanders in contact 

Found Extremely Rarely in Pirate Buried Treasure Chests

Wither Falchion

Shoots 3 Wither Skulls when Right-Clicked

Drops rarely from the Wither Skeleton Captain

Skull Crusher

Deals a lot of Extra Damage to Undead Mobs, being able to One Shot  simple Skeletons and Zombies 

Can be crafted

Skull Shatterer

Deals Extra Damage every 5th Hit

Can be crafted

Skull Scythe

Heals the player when damaging Non Undead Mobs

Can be crafted

(From Left to Right)

Deadly Seas

Damages the affected Entity while standing in Water or Rain, Ignores Armour

Curse Of Sinking

Drags Down the affected Entity  while in Water or Rain

Chaining Fangs

Spawns Evoker Fangs under the affected Entity 

Greed

Greatly Boosts Damage Dealt by affected Entity, Requires Constant Supply of Gold to not suffer Damage from it

Rampage

Given by the Skull Shatterer every 5th Hit

Curse of Armor Breaching

Significantly Reduces the Effectiveness of Armor

Old Tittle Image:

MegaPixel and Thisisnotaustin

 - For giving the idea for the captains ability