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The flag of Calico Jack Rackham. Much of Calico Jack’s fame comes from the fact that the two most famous woman pirates, Anne Bonny and Mary Read, sailed under his flag. Calico Jack got his nickname because he wore striped calico pants. Calico is an inexpensive cotton fabric that came from India.
One tale of his adventures is this one: Calico Jack and his crew were on board their vessel in a Cuban harbor, making ready to sail. Into the harbor came a Spanish warship, with a small English ship which she had captured. The Spanish attacked, but Rackam’s vessel was close in behind a little Island. The Spanish decided to wait until the morning to continue their assault. Rackam’s situation was desperate. He was outgunned, escape nearly impossible, so a daring scheme was hatched. The captured English ship close to land, so in the dead of night Calico Jack put his men into a boat, rounded the island and fell upon the sloop without being discovered. Brandishing pistols and cutlasses, they told the Spanish on board that if they made the least noise they were dead men. Rackam then made away and out to sea. The Spanish Man of War was so intent on the pirates the next morning that they made furious fire upon the now empty vessel, only later realizing that the English ship had stolen away with the pirates on board.