Calico Jack Rackham

Medium humanoid (human), chaotic neutral

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Armor Class 17 (Calico Coat)
Hit Points 104 (11d8 + 55)
Speed 30 ft.

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STR	DEX	CON	INT	WIS	CHA
15 (+2)	20 (+5)	20 (+5)	14 (+2)	12 (+1)	18 (+4)

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Saving Throws Dex +9, Cha +8
Skills Acrobatics +9, Deception +8, Persuasion +8, Stealth +9
Damage Resistances Psychic, Poison
Senses Passive Perception 11
Languages Common, Pirate’s Cant
Challenge 8 (3,900 XP)

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Traits

Evasion. When Calico Jack is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.

Jack of All Trades. Calico Jack can add half his proficiency bonus (rounded down) to any ability check he makes that doesn’t already include his proficiency bonus.

Legendary Actions. Calico Jack 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. Calico Jack regains spent legendary actions at the start of his turn.

• Quick Draw. Calico Jack makes one attack with his Cutlass.
• Commanding Presence (Costs 2 Actions). Calico Jack issues a command to one ally he can see within 30 feet of him. The ally can use its reaction to make one weapon attack or move up to its speed without provoking opportunity attacks.
• Daring Maneuver (Costs 3 Actions). Calico Jack moves up to his speed without provoking opportunity attacks and makes one attack with his Cutlass.

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Actions

Multiattack. Calico Jack makes three attacks with his Cutlass.

Cutlass. Melee Weapon Attack: +10 to hit, reach 5 ft., one target. Hit: 10 (1d8 + 6) slashing damage.

Pistol Shot. Ranged Weapon Attack: +8 to hit, range 30/120 ft., one target. Hit: 12 (2d6 + 5) piercing damage.

Daring Feint (Recharge 5–6). Calico Jack uses his action to feint. Until the start of his next turn, he gains advantage on attack rolls against one creature he can see within 30 feet of him. The target must succeed on a DC 16 Wisdom saving throw or be disoriented, granting advantage to attack rolls against it until the end of its next turn.

Swashbuckler’s Flourish (1/Short or Long Rest). As a bonus action, Calico Jack can make a Dexterity (Acrobatics) check. On a success, he can choose up to three creatures within 5 feet of him. Each target must succeed on a DC 16 Dexterity saving throw or take 21 (6d6) slashing damage and be knocked prone.

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Equipment

• Cutlass (Melee Weapon): A finely crafted pirate sword with a razor-sharp edge.
• Pistol (Ranged Weapon): A classic flintlock pistol with a limited range.
• Calico Coat (Magic Armor): A richly decorated coat with vibrant patterns, providing the following benefits:
  • AC Bonus. While wearing this coat, Calico Jack’s AC is 17.
  • Dazzling Display. As a bonus action, Calico Jack can use the coat to create a dazzling display of colors. Each creature of his choice within 30 feet must succeed on a DC 16 Wisdom saving throw or be blinded until the end of its next turn.
  • Camouflage. As a reaction, Calico Jack can blend into his surroundings, gaining advantage on Dexterity (Stealth) checks for 1 minute. This ability can be used once per short or long rest.
• Magic Item: Cloak of Protection: Grants a +1 bonus to AC and saving throws while worn.

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Lair Actions

When fighting in his lair (e.g., aboard his pirate ship during a storm), Calico Jack can use lair actions to create dramatic effects:

• Turbulent Seas. The ship rocks violently. All creatures on the ship must succeed on a DC 15 Dexterity saving throw or be knocked prone and take 7 (2d6) bludgeoning damage.
• Fog of War. Thick fog envelops the area. The area within 60 feet of Calico Jack becomes heavily obscured until the end of his next turn.
• Marauder’s Call. Calico Jack summons a spectral crew. For one round, he and his allies gain advantage on attack rolls and saving throws.

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Reactions

Riposte. When a creature misses Calico Jack with a melee attack, he can use his reaction to make a melee weapon attack against that creature.

Uncanny Dodge. When an attacker that Calico Jack can see attacks him with an attack that hits, he can use his reaction to halve the attack’s damage.

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Legendary Resistances (3/Day). If Calico Jack fails a saving throw, he can choose to succeed instead.

D&D 5E Mythological Figures: Calico Jack Rackham

D&D 5E – Mythological Figures: Calico Jack Rackham | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

Calico Jack was born John Rackham on December 26th 1682 and took up piracy in the Bahamas and Cuba throughout 1718–1720. In 1718 after Charles Vane used his rank to overturn a decision to fight a French man-of-war that Jack convinced most of the crew would be a good idea to try to overtake, Jack (his quartermaster at the time) took over the Ranger from him (leaving him and the 15 pirates with him a lesser ship and supplies). Calico Jack (so named for his choice of clothing) continued pirating—focusing on large ships near the shore and offering a place on his crew to the sailors on board—until taking a pardon in 1719, claiming that Charles Vane forced him into piracy. He met Anne Bonny not long afterward and fell in love with her, absconding with a stolen ship and violating his pardon to pirate for a while (with Mary Read also among his crew). Calico Jack’s end began one night after too much reveling, he and his crew too drunk to resist the authorities, and later that year (1720) he was executed on a tiny island near Port Royal’s main entrance, an islet that still bears his name as it was where his corpse was left hanging from the gallows.

Aside: There are some claims that Calico Jack invented the skull-and-crossbones Jolly Roger flag, but when I dug deeper I couldn’t find a strong basis for it (but good reason to think other people created it).

Design Notes: Calico Jack was more of a clever and capable manipulator than he was a brawny bandit so his build is all rogue! With a solid Dexterity and Charisma, plus killer social skill bonuses (which are extra great thanks to Reliable Talent), he should be a satisfying intrigue enemy albeit not the most spectacular combatant. Let’s do the numbers! The DMG came in at 6.75, the Blog of Holding a 7.6, and it averages out a touch above 7.

Calico Jack Rackham​

Medium humanoid (human), neutral evil rogue (mastermind) 12
Armor Class 16 (studded leather)
Hit Points 78 (12d8+24)
Speed 30 ft.

STR​	DEX​	CON​	INT​	WIS​	CHA​
12 (+1)​	18 (+4)​	14 (+2)​	14 (+2)​	11 (+0)​	18 (+4)​

Saving Throws Dex +8, Int +6
Skills Athletics +5, Deception +12, Insight +8, Investigation +10, Perception +8, Persuasion +12; navigator’s tools +6, vehicles (water) +8
Senses passive Perception 18
Languages English
Challenge 7 (2,900 XP)

Background: Nautical. Calico Jack is able to acquire passage on a sailing ship for him and his allies free of charge. He has no control over the ship’s route, departure, or return, and although no coin is required he and his companions do have to help crew the vessel.

Cunning Action (1/Turn). Calico Jack can use a bonus action to take the Dash, Disengage, Help, or Hide action.

Evasion. When Calico Jack is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.

Fast Learner. After Calico Jack has heard a creature speak for 1 minute or longer, he can mimic its manner of speaking as long as he knows the same language as the creature (allowing him to seem like he is local to a given region).

Feat: Diplomatic. Calico Jack can make a Charisma (Persuasion) check contested by the Wisdom (Insight) check of a creature that can understand what he says during 1 minute of talking. On a success, as long as Calico Jack remains within 60 feet of it (and for 1 minute afterward) the target is charmed by him. Calico Jack automatically fails on the check if he or his companions are fighting the target.

Reliable Talent. Whenever Calico Jack makes an ability check that lets him add his proficiency bonus, he can treat a d20 roll of 9 or lower as a 10.

Sneak Attack (1/Turn). Calico Jack deals an extra 21 (6d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Calico Jack that isn’t incapacitated and Calico Jack doesn’t have disadvantage on the attack roll.

Tactician. Calico Jack is able to use the Help action to aid an ally attacking a creature as long as the target of the attack is able to see and hear Calico Jack and is within 30 feet of him.

Tactician’s Insight. After Calico Jack has observed or interacted with a creature for 1 minute, he learns whether or not it has higher or lower Intelligence, Wisdom, or Charisma scores than him. In addition, he learns if the target has more or fewer class levels than him. Calico Jack also knows when he and the target have equal scores in one of these categories.

ACTIONS
Saber. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 7 (1d6+4) slashing damage.

Dagger (3). Melee or Ranged Weapon Attack: +8 to hit, reach 5 ft. or thrown 20/60 ft., one target. Hit: 6(1d4+4) piercing damage.

Pistol (2). Ranged Weapon Attack: +8 to hit, range 30/90 ft., one target. Hit: 9 (1d10+4) piercing damage.

REACTIONS
Uncanny Dodge. When an attacker Calico Jack can see hits him with an attack, he can use his reaction to halve the attack’s damage against him.

Calico Jack Rackham

Male human rogue 8 / fighter 4
Chaotic Neutral

XP: 25,600
CR: 11
Race: Human
Class: Rogue 8 / Fighter 4
Alignment: Chaotic Neutral
Init: +7 (+5 Dex, +2 Improved Initiative)
Senses: Perception +13

Defense

• AC: 21, touch 15, flat-footed 17 (+5 Dex, +4 armor, +2 dodge)
• HP: 98 (8d8 + 4d10 + 24)
• Fort: +9, Ref: +13, Will: +4
• Defensive Abilities: Evasion, Uncanny Dodge

Offense

• Speed: 30 ft.
• Melee: +1 Cutlass +14/+9 (1d8+6/18–20)
• Ranged: Masterwork Pistol +13 (1d8+4/x4, 20 ft.)
• Special Attacks: Sneak Attack +4d6, Daring Feint (once per day)

Statistics

• Str: 16, Dex: 20, Con: 16, Int: 14, Wis: 10, Cha: 18
• Base Attack Bonus: +10/+5
• CMB: +13, CMD: 28

Feats:

Improved Initiative, Weapon Focus (Cutlass), Weapon Specialization (Cutlass), Quick Draw, Two-Weapon Fighting, Combat Expertise, Improved Feint

Skills:

Acrobatics +18, Bluff +15, Climb +10, Intimidate +15, Perception +13, Profession (sailor) +12, Sense Motive +10, Stealth +18, Swim +10

Languages:

Common, Spanish, Pirate’s Cant

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Special Abilities

• Sneak Attack (Ex): +4d6 damage when flanking or when target is denied Dexterity bonus.
• Evasion (Ex): If Calico Jack makes a successful Reflex save, he takes no damage from an effect that would normally deal half damage on a successful save.
• Uncanny Dodge (Ex): Cannot be caught flat-footed or lose his Dexterity bonus to AC if the attacker is invisible.
• Daring Feint (Ex): Once per day, Calico Jack can make a Bluff check to feint in combat as a swift action, gaining advantage over an opponent, which is flat-footed until the start of his next turn.
• Bravado’s Blade (Ex): Calico Jack gains a +2 circumstance bonus on Bluff and Intimidate checks during combat.

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Combat Gear:

• +1 Cutlass: A finely crafted pirate sword with an intricate hilt (1d8+6/18–20).
• Masterwork Pistol: A well-balanced flintlock pistol (1d8+4, x4 critical).
• Calico Coat of Deflection: This magical coat acts as +2 studded leather armor and grants a +2 bonus on Reflex saves against area effects. Once per day, it can dazzle enemies in a 20-foot radius for 1d4 rounds (DC 16 Will save negates).
• Pirate’s Bandana of Allure: Grants a +2 bonus on Charisma-based skill checks.

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Lair Actions (Optional)

When aboard his ship or in a similar location, Calico Jack can use the following lair actions:

• Sea’s Fury: The area becomes difficult terrain for enemies, mimicking the rocking of a ship in a storm (DC 15 Acrobatics to avoid falling prone).
• Fog of War: Calico Jack can summon dense fog, obscuring vision within 20 feet for one round.

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Personality & Tactics:

Calico Jack is a daring, flamboyant pirate captain. His combat style is agile, favoring quick strikes and deception. He uses feints and sneak attacks to catch opponents off-guard, relying on both his swordsmanship and the firepower of his pistol. He revels in the chaos of battle, but always fights with precision and a sense of self-preservation.