When most people think of pirates, a few iconic names come to mind—Blackbeard, Captain Kidd, and of course, Calico Jack. Though his career as a pirate was relatively short, Calico Jack remains one of the most colorful figures of the Golden Age of Piracy. His name lives on not just for his deeds, but also for his infamous companions and iconic flag.

Who Was Calico Jack?

Born John Rackham around 1682 in England, Calico Jack got his nickname from the brightly colored calico clothing he preferred to wear—a bold fashion choice even for a pirate. He first emerged in the historical record in the early 18th century as part of Charles Vane’s crew, eventually taking command of his own ship in 1718 after staging a mutiny against Vane.

The Flag That Struck Fear

One of Calico Jack's lasting legacies is the Jolly Roger flag design he popularized: a skull with two crossed swords beneath it. Unlike the more familiar skull-and-crossbones, Rackham’s flag was more aggressive and dynamic—perfectly matching his audacious nature.

The Women Who Made History

Perhaps the most fascinating aspect of Calico Jack’s story is his partnership with Anne Bonny and Mary Read, two of the few documented female pirates of the era. Bonny, who was romantically involved with Rackham, disguised herself as a man to join his crew. Read, too, concealed her gender and became a formidable fighter.

Their courage and defiance of gender roles have become legendary, and their presence aboard Rackham's ship made his crew one of the most unique in pirate history.

The End of the Adventure

In 1720, Calico Jack’s pirating days came to an end. While anchored off the coast of Jamaica, his crew was surprised and captured by a British sloop under the command of pirate hunter Captain Jonathan Barnet. Most of Rackham’s crew was too drunk to put up a fight.

Rackham was tried and hanged in Port Royal in November 1720. His body was then gibbeted (hung in chains) as a warning to would-be pirates. Anne Bonny and Mary Read escaped immediate execution by claiming to be pregnant—known as “pleading the belly.”

Calico Jack's Legacy

Despite his brief career, Calico Jack Rackham left an indelible mark on pirate folklore. His flamboyant image, fearless companions, and iconic flag have made him a favorite in books, films, and video games.

While he may not have been the most successful or ruthless pirate of the high seas, Rackham’s style, story, and swagger have made him an enduring symbol of the pirate life.

⚓ Fun Fact

Did you know? The "Pirates of the Caribbean" films and the Assassin’s Creed video game series both draw inspiration from Calico Jack and his crew!

Sources:

"Pirates: A History" by Tim Travers

National Maritime Museum Archives

British Royal Navy Records, 1720