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William Jackson, “The Iron Buccaneer”

William Jackson, "The Iron Buccaneer"

William Jackson is an English privateer who in the service of the Providence Island Company captured and ransomed Spanish slave ships.

  • Alias – “The Iron Buccaneer”
  • Gender – Male
  • Race – Human
  • Occupation – Privateer, Captain of the Providence Island Company
  • Religion – Protestant
  • Allies – The Providence Island Company, other English privateers
  • Enemies – The Spanish Empire, particularly their slave ships
  • Abode/Base of operations – The Caribbean Sea
  • Nationality – English
  • Languages – English, Spanish
  • Alignment – Chaotic Neutral
  • Affiliation(s) – The Providence Island Company, English privateers
  • Significant others – None mentioned in historical records.

William Jackson, the Iron Buccaneer

Medium humanoid (human), chaotic neutral

Armor Class: 15 (leather armor)

Hit Points: 165 (22d8 + 66)

Speed: 30 ft.

STR 18 (+4) DEX 20 (+5) CON 16 (+3) INT 14 (+2) WIS 14 (+2) CHA 12 (+1)

Saving Throws: DEX +9, CON +6, WIS +6

Skills: Acrobatics +9, Athletics +8, Perception +6, Stealth +9

Damage Immunities: poison

Condition Immunities: exhaustion, poisoned

Senses: passive Perception 16

Languages: Common, Spanish

Challenge: 12 (8,400 XP)


Multiattack: William Jackson can make three melee attacks.

  • Rapier: Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 7 (1d8 + 3) piercing damage.
  • Pistol: Ranged Weapon Attack: +9 to hit, range 30/90 ft., one target. Hit: 11 (2d10) piercing damage.
  • Cutlass: Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 5) slashing damage.

Legendary Actions

William Jackson 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. William regains spent legendary actions at the start of his turn.

  • Parry: William adds 5 to his AC against one melee attack that would hit him. To do so, William must see the attacker and be wielding a melee weapon.
  • Disarm (Costs 2 Actions): William Jackson makes one cutlass attack and attempts to disarm the target. The target must succeed on a DC 17 Strength saving throw or drop one item of William’s choice that it’s holding.
  • Quick Shot (Costs 3 Actions): William makes one pistol attack as a bonus action.


  • Leather armor
  • Rapier
  • Cutlass
  • Flintlock pistol (x2)
  • 20 bullets
  • 20 gold coins
  • Eye patch
  • Compass
  • Spyglass

Magic Items

  • Ring of Free Action: William Jackson is unaffected by difficult terrain and spells that would reduce his speed or restrict his movement.
  • Cape of the Mountebank: William can use an action to cast the Misty Step spell.
  • Amulet of Health: William’s Constitution score is 19 while he wears this amulet.

Lair Actions

On initiative count 20 (losing initiative ties), William can take a lair action to cause one of the following effects:

  • William Jackson orders his crew to fire a volley of cannonballs at a target. The target must make a DC 17 Dexterity saving throw, taking 44 (8d10) bludgeoning damage on a failed save, or half as much damage on a successful one.
  • William issues a command to his crew, granting them advantage on their next attack roll.
  • William shouts a rallying cry, giving himself and all friendly creatures within 60 feet temporary hit points equal to his level + his Charisma modifier (minimum of 1 temporary hit point).

William Jackson is a bold and daring English privateer with a passion for the sea and a deep desire for adventure. He is a tall and broad-shouldered man with a thick beard and intense blue eyes. He has weathered skin and scars on his face, evidence of the dangers he has faced at sea. His thick, curly hair is usually tied back in a ponytail, and he wears a tricorn hat with a feather. He has a commanding presence and moves with confidence and purpose.

Born to a family of fishermen, William Jackson has always felt a powerful connection to the ocean, and from a young age he dreamed of sailing the high seas and making his fortune as a sailor. As soon as he was old enough, he joined the British Navy and spent several years serving his country in various conflicts around the world.

But William grew restless with the rigid structure and discipline of naval life, and he longed for the freedom and excitement of privateering. So, he left the Navy and joined the Providence Island Company, a group of English investors who had established a colony in the Caribbean and were authorized to engage in acts of piracy against the Spanish.

With his sharp mind, quick reflexes, and fierce determination, William quickly became one of the most successful privateers in the company’s service. He led daring raids against Spanish galleons and captured and ransomed countless slave ships, earning a reputation as a ruthless and cunning pirate who could outmaneuver even the most skilled Spanish captains.

But for William, privateering was more than just a way to make money – it was a chance to live life on his own terms and to seek adventure and excitement in a world that was all too often dull and mundane. He dreams of one day retiring to a life of leisure, with enough money to never have to worry about where his next meal will come from.

Despite his rough exterior and his willingness to engage in acts of piracy, William has a strong sense of honor and a deep respect for the sea and those who sail upon it. He is a man of few words but deep convictions, and those who earn his loyalty and trust will find in him a fierce and unyielding ally.

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