John Rackham was one of the rank-and-file pirates based in the Bahamas and, at the time of Woodes Rogers‘ arrival there, was serving in the crew of Charles Vane, leader of the die-hard pirate faction. He had a penchant for wearing clothes made from bright Indian Calico cloth, which lead his fellow pirates to dub him Calico Jack Rackham. Nothing is known of his background prior to becoming a pirate.
By November, 1718, Rackham was serving as Vane’s quartermaster aboard an unnamed brigantine. On the 23rd of that month, Vane was voted out of power by his crew for refusing to engage a French man-of-war in the approaches to the Windward Passage. Calico Jack was chosen as his replacement and Vane and fifteen loyalists left the ship’s company in a small boat.
Rackham’s command was not particularly successful, showing courage, but a lack of judgement. He chose to cruise around Jamaica, the center of British power in the Caribbean and the headquarters of the Royal Navy’s West Indies squadron. In December he captured a richly-laden merchant ship (the Kingston) within sight of Port Royal, provoking the merchants there to outfit several privateers to apprehend him. Three months later, the found Rackham at Isla de los Pinos, south of Cuba, still in his brigantine with the Kingston anchored alongside; Rackham and most of his crew were dozing ashore in a camp of tents made from old sails, and hid in the woods while their ships were captured.
Left without vessels, Rackham and six followers sailed around Cuba to Nassau in a small boat, a trip that took them nearly three months. Claiming they had been forced into piracy by Vane, they convinced Governor Rogers to pardon them.
Rackham settled in Nassau, where he entered into a passionate affair with Anne Bonny, the fiery young wife of John Bonny, a pirate who had turned informer. In mid-1720, the lovers approached John and convinced him to annul their marriage in exchange for a cash payment. Unfortunately, Rogers refused to countenance the arrangement. Unable to continue their relationship ashore, Rackham and Bonny decided to return to piracy. The couple recruited a half-dozen ex-pirates and one of Anne’s close friends, a cross-dressing female sailor named Mary Read, stole a swift sloop, and snuck out of Nassau on the night of August 22, 1720.
Rackham’s second command fared no better than the first. In October, he again led his party to Jamaica, where they recklessly cruised along the shore, sacking vessels from harbor to harbor. Again, privateers caught up to him and, after a short engagement, took Rackham and his serving crew into custody. He was found guilty and hung at Gallows Point in Port Royal on November 18, 1720. His body was later placed in a gibbet on a small sandbar in the harbor now known as Rackham’s Cay.