Story of Jack Rackham - Calico Jack


Jack Rackham, whose real name was John, was known as “Calico Jack” because of his shiny, sumptuous calico clothes. He was not exactly the most famous pirate, nor the most feared, nor even the most successful. Rackham, on the other hand, was undoubtedly the most elegant pirate in the history of piracy. But this buccaneer is remembered not only for his clothes, but also for a characteristic considered very ominous at the time: the presence of women in the crew.

Jack Rackham

Author of the pirate flag called Jolly Roger, the most famous of them all, his fame is overshadowed by other contemporary buccaneers who are much more famous, among whom Blackbeard or Samuel Bellamy deserve to be mentioned. Few people know, however, that this elegant adventurer (in his own way) was the model for one of the most famous fictional pirates: Jack Sparrow from the “Pirates of the Caribbean” movie series. Let’s discover together the exciting story of this movie pirate.


The era of the Corsairs

In the second half of the 17th century, the Caribbean was almost completely under Spanish rule, at least in appearance. The mainland (Venezuela, Costa Rica, Nicaragua, Mexico and Panama) as well as the islands of Cuba and Puerto Rico, and the eastern part of Hispaniola, were all under its control (what is now called the Dominican Republic). Some areas, however, belonged to other European nations. For example, France controlled the western part of Hispaniola (what is now Haiti), the United Kingdom controlled Jamaica and the Bahamas, and an arc of islands stretching from Puerto Rico to the Venezuelan coast had French, English, Dutch and even Danish possessions. In this context, and given the obvious desire of European countries to disrupt the commercial domination of Spain in America, the figure of the privateer appeared in 1650.

Pirate Ship Jack Rackham

A privateer is simply a pirate working for a government who attacks ships of other countries with which that country is at odds, officially or unofficially. These governments issue certain individuals a document called a “Letter of Marque“, which allows them to engage in piracy against enemy ships. The majority of them were based in Tortuga, a small island near Hispaniola. Not only did these privateers attack ships, but they also assaulted and pillaged cities (Cartagena, Panama, Guatemala…). However, around 1680, European governments stopped granting letters of marque to privateers, and this way of life gradually disappeared.

The beginning of the pirate era

Golden age of privacy

However, the beginning of the War of the Spanish Succession in 1701 revived the phenomenon, especially on the British side, as English privateers felt safe in the absence of Spanish and French warships able to face them, most of them being engaged in European warfare. This position persisted until 1712, when England ceased its war with Spain. Faced with the prospect of losing their livelihood, many privateers turned to piracy. Some of them went to the sparsely populated islands of the Bahamas, settling in New Providence, the largest island in the archipelago. Thus began the “Golden Age of Piracy”, a period of wealth for them that lasted from 1715 to 1725. The authority of pirates in the Bahamas became undeniable, and names such as Edward Teach (alias “Blackbeard”), Stede Bonnet, Samuel Bellamy and one of the heroes of our history, Charles Vane, began to distinguish themselves.


Rackham’s beginnings with Charles Vane

Who is Jack Rackam ? Apart from the fact that he was born on December 26, 1682 in Bristol, England, we know little about the early life of Jack Rackham. The first mention of him dates back to 1718, when he was a boatswain on board the ship “Ranger” with the terrible Charles Vane. That year, King George I of England sent Woodes Rogers, a former pirate captain, to the Bahamas with the mission of granting a “royal pardon” for pirates who wished to be rehabilitated and four ships to pursue those who refused. Charles Vane, one of the unrepentant pirates, retreats to open waters and promises to wage war on all repentant pirates.

Charles Vane and Jack Rackham

Charles Vane was a terrible commander. Even when the crews of the targeted ships had already surrendered without a fight, he is accused of endless cruelties (for example, it is said that he tied the captain of a captured ship by the hands and feet and hung him from a pole, forcing the men to test their aim with him). His failure to share the spoils of his plunder fairly was certainly the worst sin for his crew. It was only a matter of time before he fell, and that happened when he escaped from a French warship he had tried to attack. His boatswain, Jack Rackham, accused Vane of cowardice and encouraged the crew to revolt and elect him captain, which they dutifully did. Vane was left on a drifting ship with a few loyal soldiers.

The birth of Captain Calico Jack

Calico Jack

Among all the pirates who patrolled these waterways, the new captain stood out for something very special: his attire. He liked to wear a shirt and pants made of calico, a brightly printed cotton fabric. That’s why he was nicknamed “Calico Jack. After taking command of the “Ranger” and realizing that he was wanted by the law, Jack Rackham focused on small boats and fishing vessels near Jamaica, Cuba and the Leeward Islands. And to tell the truth, he did not do badly since his strategy was largely successful.

However, his greatest achievement came when he captured a brig called “Kingston” near Jamaica and discovered enormous treasures on board. Unfortunately for him, the news spread quickly and the merchants of Port Royal sent bounty hunters in search of Jack Rackham, who had been cornered on the Isle of Pines (today’s Isle of Youth, in southwest Cuba).

Calico Jack Rackham

When Jack Rackham and his men were cornered, they abandoned their ship and fled into the jungle, where the ships sent against them fled with all the loot. However, luck did not completely abandon him, his cunning allowed him to steal an English sloop named “Revenge” which had been captured by the Spanish coast guard. He decided to set sail for New Providence (in the Bahamas) while there was still time, knowing that the life of a pirate was extremely perilous and that it was only a matter of time before he ended up at the end of a rope.


The meeting with Anne Bonny

Anne Bonny and Calico Jack

Jack Rackham returns to New Providence and officially asks for a royal pardon from Woodes Rogers, the new governor of the Bahamas. He states that his former captain, Charles Vane, forced him to become a pirate, despite the fact that he had no desire to do so. We don’t know if it was out of naivety or Rogers’ animosity for Vane that the governor finally granted Jack Rackham a pardon in 1719, freeing him from all charges of piracy.

Jack Rackham then resided in New Providence awaiting his pardon, and when he had nothing better to do, he spent his evenings in the harbor pubs recounting his escapades. He met a woman named Anne Bonny in one of these bars and immediately began courting her. The woman, who was known for her beauty as well as her violent personality, returned the favor and the two began dating. Jack Rackham squandered much of his money on her, and Anne became pregnant soon after. Unfortunately for both lovers, Anne Bonny was married and in those days adultery was a serious crime.

The escape of the lovers Jack and Anne

Calico Jack pirates

Their love story became public and the governor threatened to have Anne whipped for adultery. Confronted with this difficult situation, Anne persuades Rackham to kidnap her, to gather a crew and to steal a boat to escape. Jack Rackham, infatuated with the beautiful Anne, is persuaded and enlists the help of a band of unemployed pirates to follow them, seizing a corvette from a local merchant named John Ham.

They set sail for Cuba, where Anne gave birth to their first child. At the time, the presence of a female pirate in the crew was a bad omen for the crew. Short of money, Calico Jack asked Anne Bonny to leave the child in the hands of some of the woman’s friends and to join him in his adventures, dressed as a man and calling himself Adam Bonny. Thus begins his second stage as a pirate, this time as a couple, and only a few months after being pardoned for his previous transgressions.

Anne Bonny


Jack’s greatest booty

This time, Jack Rackham’s tactics are quite similar to the ones he used before: he attacks small ships to plunder the little booty they can carry. The capture of three ships carrying gold and jewels from a wealthy Spanish family from Matanzas to Cayo Esquivel was his greatest treasure. After ambushing two of them, Rackham sank them and pursued the main ship, which surrendered immediately after seeing the black pirate flag. Jack Rackham, suspicious of the maneuver, attacked the ship with considerable ferocity, killing everyone on board. After this great catch, it is said that he disembarked with the treasure and buried it in an unknown place in Cuba.

Jack Rackham Anne Bonny

The meeting with Mary Read

For several months, Jack Rackham and his crew became the terror of the waters between Cuba and Jamaica, without any of the ships sent to find him succeeding. Crewman Adam Bonny fought alongside the rest of the crew and, in some cases, more fiercely and bravely. The fact that he shared the captain’s quarters was insignificant compared to his bravery in battle, after all, everyone has flaws. It was at this time that they plundered the cargo of a merchant ship. A handsome young man named Mark Read was part of the crew of the merchant ship, and he begged Jack Rackham to join his crew. Calico Jack agreed (this is standard procedure for short-handed pirate ships). In reality the boy turns out to be a woman named Mary Read, not a boy.

Mary Read

Anne discovered Mary’s secret and the two became great friends, so much so that Rackham felt jealous and demanded an explanation of Anne’s closeness to the new crewman. When Mary admitted that she was a woman, Rackham then allowed her to stay with the rest of the crew, where, like Anne, she displayed bravery that was often superior to that of her companions. Mary eventually fell in love with a member of the crew and the two were married according to pirate rituals.


Origin of the pirate flag

The “Jolly Roger“, a pirate flag, is one of the first things that comes to mind when we think of pirates. In theory, privateers flew these flags, which were red (“Red Jack”) by order of the British Admiralty, ostensibly to signify bloodshed if the attacked ship did not surrender without a fight. “No life will be spared, no questions asked,” the color read, clearly stating the intentions of the privateers. Its color soon changed to black, however (although some later pirates, such as Christopher Moody, kept the original red).

Calico Jack Flag

Calico Jack’s Jolly Roger, the true emblem of piracy

Almost all pirates had their own Jolly Roger, but the one with the skull and crossbones underneath, which we owe to the pirate Sam Bellamy, is probably the most famous. The flag flown by Jack Rackham, which replaced the two shins with two crossed swords, was no less legendary. This Jolly Roger has become over time one of the most recognizable pirate flags, and it is the one found in the “Pirates of the Caribbean” saga. In theory, one might think that flying such a flag, which clearly indicates the objectives of the ship carrying it, is not a good idea. However, the mere sight of one of these flags appearing on the horizon terrified the crews of attacked ships, who often surrendered without a fight. This is one of the first examples of psychological warfare in history.

Jack Rackham Flag

The origin of the phrase Jolly Roger is unclear, and many explanations have been proposed to explain it. However, it seems that the correct answer is that it is a variation of “Old Roger“, the original name of the flag. In the English language, the word “Old Roger” refers to the Devil. As a final detail, add that after Jack Rackham’s death, Anne Bonny received all of his possessions, including his ship and flag, and that he altered the design of the flag by replacing one of the swords with a rifle, in honor of his friend Mary Read.


The defeat of Rackham

Jack Rackham’s exploits prompted the governor of Jamaica, Richard Lawes, to send a pirate hunter named Jonathan Barnet in search of him (among them, the capture of the corvette “William” moored in Nassau, Bahamas). Barnet discovered Rackham’s ship in Nigril Bay (Jamaica) in October 1720 and cornered it. Rackham’s ship fired a cannon after being ordered to surrender, to which Barnet replied with a salvo that inflicted considerable damage. With the exception of Anne Bonny and Mary Read, who fought like wild animals before being arrested, most of the crew of Rackham’s ship were drunk and did not resist capture very much.

Death Calico Jack Rackham

Death Calico Jack Rackham

Jack Rackham and his men are then arrested and sent to Spanish Town, the capital of Jamaica at the time. Anne Bonny and Mary Read were spared from prosecution, because they claimed to be expecting a child (their argument was the anthology phrase “we plead for our wombs, sir”). On November 16, 1720, the rest of the pirate crew was sentenced to be hanged and the sentence was carried out the next day. Despite her status as a prisoner, Anne Bonny was allowed to visit Jack Rackham in his final hours, however her last remarks to him were the strong ones:

“I’m sad to see you like this, Jack, but you wouldn’t be hung like a dog today if you had fought like a man”.

Thus died one of the most fascinating, yet inglorious pirates in the history of piracy. Jack Rackham’s body was wrapped and placed in a cage after his death as a warning to future pirates. The place where it was displayed is now known as Dead Man Cay, although it was later renamed Rackham Cay. Jack Rackham’s last words, according to legend, were “Woe to him who finds my many treasures, for no ship can carry them all,” although this is more myth than fact.

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