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Calico Jack Rackham

Rackham, Jack, aka Calico Jack, Pirate of the Caribbean, 18th century lithography. Calico Jack Rackham
Rackham, Jack, aka Calico Jack, Pirate of the Caribbean, 18th century lithography.

English pirate captain, his nickname is derived from the colourful calico clothes he wears. He has two things going for him that ensures he is known as more than a well dressed pirate; Anne Bonny and Mary Read.

After deposing Charles Vane from his captaincy, Rackham cruised the Leeward Islands, Jamaica Channel, and Windward Passage. He accepted a pardon and moved to New Providence, where he met Anne Bonny, who at the time was married to James Bonny. When Rackham returned to piracy, Bonny joined him. Their new crew included Mary Read.

In service

Jack served as quartermaster on Charles Vane’s sloop Ranger, operating out of the ‘Pirates’ republic’. After robbing several ships, Vane and his crew encountered a large French man-o-war.

The ship, which was at least twice as large as Vane’s sloop, went after them. Vane, claiming caution as his reason, commanded a retreat from battle. Jack Rackham quickly spoke up and contested the decision, suggesting they fight the man-o-war, because it would have plenty of riches. In addition, he argued, if they captured the ship, it would place a much larger ship at their disposal. Of the approximately ninety men on the ship, only fifteen supported Vane in his decision. Despite the overwhelming support for Rackham’s cry to fight, Vane declared that the captain’s decision is considered final and they fled the man-o-war.

Rackham called a vote in which the men branded Vane a coward and removed him from the captaincy, making Calico Jack the next captain. Rackham gave Vane, and fifteen supporters, the other sloop in the fleet, along with a decent supply of ammunition and goods.

As captain

Pirate flag of Jack Rackham (Calico Jack)
Pirate flag of Jack Rackham (Calico Jack)

Once gaining the captaincy Rackham made a career of plundering small vessels close to shore.

He captured the merchant ship Kingston. The Kingston had a rich cargo, and promised to be a big score for Rackham and his crew. Unfortunately for him, the Kingston had been taken within sight of Port Royal, where outraged merchants outfitted bounty hunters to go after him. They caught up with him while his ship and the Kingston were anchored at Cuba. Rackham and most of his men were on shore at the time, and while they escaped capture by hiding in the woods, their ship – and their rich trophy – was taken away.

Rackham and his men were still stranded at at a town in Cuba, when a Spanish warship charged with patrolling the Cuban coast entered the harbour, along with a small English sloop they had captured. The Spanish warship saw the pirates but could not get at them at low tide, so they parked in the harbour entrance to wait for morning. That night, Rackham and his men rowed over to the captured English sloop and overpowered the Spanish guards there. As dawn broke, the warship began blasting the town, now empty, as Rackham and his men silently sailed past in their new prize.

Rackham and his men made their way back to Nassau, where they appeared before the Governor and asked to accept the royal pardon, claiming that Vane had forced them to become pirates. The Governor, who hates Vane, believed them and allowed them to accept the pardon and stay. Their time as honest men will not last long.

Anne Bonny

While in port, Rackham began an affair with Anne Bonny, wife of sailor James Bonny, who was employed by the Governor. After finding out about the relationship, James Bonny brought Anne to Governor Rogers, who ordered her whipped on charges of adultery. Rackham offered to buy Anne in a “divorce by purchase,” but she refused to be sold like an animal. The pair (with a new crew) plan to escaped to sea together, voiding Rackham’s pardon.

The design of Rackham’s Jolly Roger flag was seen in the 1995 film Cutthroat Island and the 2003 film Pirates of the Caribbean: The Curse of the Black Pearl.

D&D 5E Mythological Figures: Calico Jack Rackham

Calico Jack Rackham DnD 5e BANNER.jpg

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.

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.

Calico Jack Rackham
Human CR 12
XP 19200
Any Medium humanoid
Swashbuckler level 6 (skill points 36) Swashbuckler, Rogue level 10 (skill points 100) Rogue (Pirate)
Init +4; Senses ; Perception +19
AC 18, Touch 14, flat footed 14 (+3 Quilted Cloth) (+2 Dexterity, +4 armour, +2 feats)
hp 104 (0d8+6d10+10d8+6+16);
Fort +5, Ref +14, Will +7
Speed 30
Single Attack(+1/+0) Rapier +18 (1d6+4/15-20) or (+1/+1) Pistol +17 (1d8+1 X4)
Full Attack (+1/+0) Rapier +18/13/8 (1d6+4/15-20) or (+1/+1) Pistol +17 (1d8+1 X4) range 20
Space 5ft.; Reach 5
Special Attacks
Menacing Swordplay (Ex) At 3rd level, while she has at least 1 panache point, when a swashbuckler hits an opponent with a light or one-handed piercing melee weapon, she can choose to use Intimidate to demoralize that opponent as a swift action instead of a standard action.Opportune

Parry and Riposte (Ex) At 1st level, when an opponent makes a melee attack against the swashbuckler, she can spend 1 panache point and expend a use of an attack of opportunity to attempt to parry that attack. The swashbuckler makes an attack roll as if she were making an attack of opportunity; for each size category the attacking creature is larger than the swashbuckler, the swashbuckler takes a -2 penalty on this roll. If her result is greater than the attacking creatures result, the creatures attack automatically misses. The swashbuckler must declare the use of this ability after the creatures attack is announced, but before its attack roll is made. Upon performing a successful parry and if she has at least 1 panache point, the swashbuckler can as an immediate action make an attack against the creature whose attack she parried, provided that creature is within her reach.  Sneak Attack Sneak attack at an extra (D6) 5

Swashbuckler Initiative (Ex) At 3rd level, while the swashbuckler has at least 1 panache point, she gains a +2 bonus on initiative checks. In addition, if she has the Quick Draw feat, her hands are free and unrestrained, and she has any single light or one-handed piercing melee weapon that isn’t hidden, she can draw that weapon as part of the initiative check.

Swashbuckler Weapon Training (Ex) At 5th level, a swashbuckler gains a +1 bonus on attack and damage rolls with one-handed or light piercing melee weapons. While wielding such a weapon, she gains the benefit of the Improved Critical feat. These attack and damage bonuses increase by 1 for every 4 levels beyond 5th level (to a maximum of +4 at 17th level).Bonus =+ 1
Strength 13, Dexterity 14, Constitution 11, Intelligence 12, Wisdom 11, Charisma 17
Base Attack 13 CMB 14 ; CMD 28
Feats: Weapon Specialization, Another Day (Ex), Assault Leader (Ex), Bleeding Attack, Fast Stealth, Armour Prof Light, Critical Focus, Dodge, Evasion, Exotic Weapon Prof, Improved Critical, Iron Will, Sea Legs, Simple Weapon Proficiency, Skill Focus (Stealth), Toughness, Weapon Finesse, Weapon Focus, Weapon Focus (Ranged);
Skills Acrobatics 25, Appraise 11, Bluff 13, Climb 24, Craft 1, Diplomacy 8, Disable Device 12, Disguise 13, Escape Artist 7, Intimidate 13, Know Dungeon 1, Know Geography 5, Know Local 11, Know Nobility 1, Linguistics 11, Perception 19, Perform 7, Profession 0, Ride 2, Sense Motive 9, Sleight of Hand 11, Stealth 27, Swim 8, Use Magic Device 12
Languages Common
Charmed Life (Ex) At 2nd level, the swashbuckler gains a knack for getting out of trouble. Three times per day as an immediate action before attempting a saving throw, she can add her Charisma modifier to the result of the save. She must choose to do this before the roll is made. At 6th level and every 4 levels thereafter, the number of times she can do this per day increases by one (to a maximum of 7 times per day at 18th level). 4Deeds Swashbucklers spend panache points to accomplish deeds. Most deeds grant the swashbuckler a momentary bonus or effect, but some provide longer-lasting effects. Some deeds remain in effect while the swashbuckler has at least 1 panache point, but do not require expending panache to be maintained. A swashbuckler can only perform deeds of her level or lower. Unless otherwise noted, a deed can be performed multiple successive times, as long as the swashbuckler has or spends the required number of panache points to perform the deed.  

Derring-Do (Ex) At 1st level, a swashbuckler can spend 1 panache point when she makes an Acrobatics, Climb, Escape Artist, Fly, Ride, or Swim check to roll 1d6 and add the result to the check. She can do this after she makes the check but before the result is revealed. If the result of the d6 roll is a natural 6, she rolls another 1d6 and adds it to the check. She can continue to do this as long as she rolls natural 6s, up to a number of times equal to her Dexterity modifier (minimum 1).

Dodging Panache (Ex) At 1st level, when an opponent attempts a melee attack against the swashbuckler, the swashbuckler can as an immediate action spend 1 panache point to move 5 feet; doing so grants the swashbuckler a dodge bonus to AC equal to her Charisma modifier (minimum 0) against the triggering attack. This movement doesn’t negate the attack, which is still resolved as if the swashbuckler had not moved from the original square. This movement is not a 5-foot step; it provokes attacks of opportunity from creatures other than the one who triggered this deed. The swashbuckler can only perform this deed while wearing light or no armor, and while carrying no heavier than a light load. Evasion Reflex save no damage instead of 1/2 Improved Uncanny Dodge Can no longer be flanked

Kip-Up (Ex) At 3rd level, while the swashbuckler has at least 1 panache point, she can kip-up from prone as a move action without provoking an attack of opportunity. She can kip-up as a swift action instead by spending 1 panache point. Nimble (Ex) Gains a dodge bonus to AC while wearing light or no armor. Anything that causes the gunslinger to lose her Dexterity bonus to AC also causes the gunslinger to lose this dodge bonus. Bonus = + 1

Panache (Ex) More than just a lightly armored warrior, a swashbuckler is a daring combatant. She fights with panache: a fluctuating measure of a swashbucklers ability to perform amazing actions in combat. At the start of each day, a swashbuckler gains a number of panache points equal to her Charisma modifier (minimum 1). Her panache goes up or down throughout the day, but usually cannot go higher than her Charisma modifier (minimum 1), though feats and magic items can affect this maximum. A swashbuckler spends panache to accomplish deeds (see below), and regains panache in the following ways.

Critical Hit with a Light or One-Handed Piercing Melee Weapon: Each time the swashbuckler confirms a critical hit with a light or one-handed piercing melee weapon, she regains 1 panache point. Confirming a critical hit on a helpless or unaware creature or a creature that has fewer Hit Dice than half the swashbucklers character level doesn’t restore panache.

Killing Blow with a Light or One-Handed Piercing Melee Weapon: When the swashbuckler reduces a creature to 0 or fewer hit points with a light or one-handed piercing melee weapon attack while in combat, she regains 1 panache point. Destroying an unattended object, reducing a helpless or unaware creature to 0 or fewer hit points, or reducing a creature that has fewer Hit Dice than half the swashbucklers character level to 0 or fewer hit points doesn’t restore any panache. Reduce Class Feats reduce by 1 Sea Legs (Ex) Gains feat

Swashbuckler Finesse (Ex) At 1st level, a swashbuckler gains the benefits of the Weapon Finesse feat with light or one-handed piercing melee weapons, and she can use her Charisma score in place of Intelligence as a prerequisite for combat feats. This ability counts as having the Weapon Finesse feat for purposes of meeting feat prerequisites.

Swinging Reposition (Ex) In light armor on ship can reposition. After making a charge or bull rush, can move 5 ft

Uncanny Dodge Retains Dexterity bonus if flat footed

Unflinching (Ex) saving throws against fear and mind-affecting effects bonus = 3
Environment Any
Organization Company 10-20, Band 30-100, Squad 4-8
Treasure Standard
ITEMS (max value 16350), Total Value = 16250
+3 Quilted Cloth (9150gp), Horn of fog – (2000gp), Ring of Swimming (5) +5 swim (2500gp), Masterwork Rapier (300gp). +1 Pistol (2300gp)
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