Bless John "Calico Jack" Rackham. If you step back and look at the picture that history paints, he's actually a model for the modern mythology of a Golden Age pirate. Reputed to be charming and handsome, he took on a moniker (given, the story goes, because he favored cotton breeches with "strypes") that has come down to us as the quintessential pirate name. There would be no Jack Sparrow were it not for Jack Rackham. Glorious indeed.
But step up to the microscope and the picture turns from rosy to gunmetal gray. Rackham was nothing more than a small time bootlegger who blew his first command and sought comfort in booze and ladies. The ladies in question, Anne Bonny and Mary Read, are probably the only reason that Calico Jack's name is so widely known today. I'm not sure that's the way he would have wanted it.
John Rackham was probably a child of England's colonies in America but where and when he was born is anyone's guess. Most historians say the Carolinas or Jamaica late in the 17th century. His name first appears historically in 1718 when he is serving as quartermaster aboard pirate Charles Vane's sloop. When Rackham accused Vane of cowardice, the crew agreed. They elected Rackham Captain and put Vane in a small boat with a few loyal men before sailing off.
Rackham headed out for Cuba, which he seems to have always favored as a base, and probably managed to lose his sloop when his crew went ashore. Again this is not a verifiable story but one way or another Rackham ended up in New Providence without a ship just as Governor Woodes Rogers was handing out pardons. Rackham took his and may have made a go of an honest life.
Around the same time, Rackham met pretty Anne Bonny and her husband James. The Bonnys were in New Providence seeking their fortune (James, who is so much of a cypher that one wonders if he ever really existed, is alternatively called a sailor or a pirate). Rackham and Bonny appear to have been attracted to each other, but whether this had to do with love or money is open to speculation. Bonny, in full female dress, boarded Rackham's ship in early 1719. Their plan was a return to piracy.
Rackham's success and failures throughout the year are not catalogued but at some point, Mary Read joined his crew disguised as a man. I won't go into the details of that full-blown fiction as you can read it here. Read was found to be a woman, some say through a friendship with Anne, and Rackham's crew seems to have taken it all in stride. Rackham took some smuggling vessels and/or fishing boats off Cuba, and was back in Nassau by the summer of 1720.
For reasons one can only speculate about, Rackham stole the sloop William and sailed out of Nassau harbor with his crew, including the lady pirates, that same summer. Rackham's escapade was ill timed. Governor Rogers was out for blood and he would not tolerate any backsliding by pirates who had taken his pardon. In August of 1720 he issued a proclamation against Rackham that listed "...Anne Fulford, alias Bonny and Mary Read."
Cruising the coast of Jamaica this time, Rackham got himself into hot water with Governor Lawes when he bungled a raid on a sugar plantation or boat builder (there is no definitive documentation other than a mention of "...Rackham, pirate, raid by land"). Lawes sent privateer Captain Johnathan Barnet to bring William and her crew to justice.
On October 22, Barnet found William hove to in Negril Bay. The crew was celebrating the taking of a fishing vessel found to be smuggling a huge cash of rum. By the time Barnet called for Rackham to surrender, everyone aboard William with the exception of her distaff side was drunk. Barnet boarded and got resistance only from Bonny and Read. By the next day William's crew was under arrest. Their trials for piracy began November 16.
Rackham's fate is, by now, old news. Convicted, he was hanged at Deadman's Cay near Port Royal, Jamaica. His body was tared and gibbeted for display and the spot where he died is now called Rackham's Cay. Anne and Mary, of course, went on to plead pregnancy and escape hanging; Mary via death by fever, Anne, it is widely speculated, via the help of her rich father.
Calico Jack Rackham's career as a pirate seems to be a microcosm of what most pirates would have known. Drunken highs upon capturing a small prize, hungry lows on land and nothing to show for it at the end. His charm left us his name and his "stryped" breeches. And of course, his love for the ladies. Considering that we still know that much, maybe it's enough.