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D&D 5E Mythological Figures: Calico Jack Rackham

Once more Mythological Figures delves into the Golden Age of Piracy with one of its most famous ne’er-do-wells: Calico Jack Rackham!

Once more Mythological Figures delves into the Golden Age of Piracy with one of its most famous ne’er-do-wells: Calico Jack Rackham!

Calico Jack Rackham DnD 5e BANNER.jpg

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.
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.

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.

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.

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Mike Myler

Mike Myler


"[A]nd at their head, all in snowy white from breeches to head-kerchief, big as a house-side and nimble as a cat, Calico Jack Rackham, none other, cautiously edging his brutally handsome, square-chinned face round a corner [...] First among equals was Calico Jack, by reason of being literate and smart and able to navigate and do all things shipshape and Bristol fashion, look'ee, as his admiring associates often agreed. Also he was strong enough to break a penny between his fingers, which helps, and having served a turn in the Navy, he was reckoned dependable. In our day he would have been a paratroop sergeant, or a shop steward, or a moderate Labour M.P. He was a pirate because it offered a profitable field for his talents, and he was saving for his old age.


"Rackham, methodical as always, had parcelled up his calicoes for the dry-cleaners, checked the share prices, paid his subscription to [the Nautical Union of Piratical Employees], and forwarded his piece of the Madagascar crown by registered post to his faithful paramour, Anne Bonney, on their shark-infested island retreat, with instructions to hold on to it carefully until he had made up his mind between the Mosquito Coast Building Society and the Harvest o' the Seas Investment Trust (Cayman Islands) Ltd."

George MacDonald Fraser, The Pyrates

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