The Real Pirate Calico Jack

The Real Pirate Calico Jack

John “Jack” Rackham, more commonly known as Calico Jack, was an English pirate captain who earned his nickname by wearing clothing with colorful calico prints. He plundered his way along the high seas during the early part of the 18th century, which happened to be during the “Golden Age of Piracy”. Like countless other pirates in history, Calico Jack met an untimely death; however his short stint as a pirate had an enormous and lasting impact on the image of pirates that still continues to this day. His personal life also earned him fame, as he was one of the only captains recorded to have female crew members, one of whom also happened to be his lover.

The Jolly Roger Flag

He is most famous for designing the Jolly Roger flag, which featured a black background and a white human skull with two white swords crossed underneath it. This image is now synonymous with pirates and everything they stand for, although most other flag designs at the time that he was alive pictured full human skeletons using various weaponry. The crisp visual impact of his simple yet effective design conveyed a message of fear to the ships’ targets that has endured for centuries. Flags were an important part of pirate culture; pirate ships would fly certain flags to communicate their intentions or to play tricks on ships that they were approaching in order to leave their soon-to-be victims more vulnerable to their attacks. This afforded many pirate ships a great deal of power, whether it was illusion or reality.

Career in Cuba and the Bahamas

Calico Jack’s career as a pirate mainly centered on Cuba and the Bahamas. Although he began innocently enough as a quartermaster on an English ship, he eventually deposed the captain and took over his position. He quickly decided that turning to piracy was a lucrative move and the crew on his ship readily agreed, motivated by the fortune they had just overtaken.

For love of a woman

Although he accepted an offer of pardon in 1719 and relocated to New Providence, he quickly returned to his life of piracy. He fell in love with a married woman named Anne Bonny, who soon ran away to join him and his crew in their exploits. Reportedly enchanted by her charms, he showered her generously with gifts. Their affair eventually was exposed, which led to threats against Anne because of her adultery. Calico Jack refused to leave her behind to her fate, and so the couple hatched a plan to steal a sloop and run away together. Worried that a crew might take issue working with a woman, she disguised herself as a man, called herself Adam and blended in with her male counterparts, working hard and fighting their enemies when necessary. Calico Jack was a unique captain in that he also employed another female crew member, Mary Read, who also passed herself off as a man to the rest of the crew.

Although his pirate exploits eventually caught up with him when he was captured in Jamaica and hanged, legendary Calico Jack was clearly ahead of his time!