Calico Jack: A Pretty Bad Pirate
Just as good as Calico Jack
Today we’re continuing our pirate series and talking about Calico Jack, the pirate who betrayed his captain and then went on to have his own adventures.
There are plenty of pirates who are well-known because of their accomplishments, Blackbeard, Captain Morgan, and if you read our last pirate article; Charles Vane, but then you have John Rackham. Eventually becoming known as Calico Jack, not because he carried around a calico cat, but because of his fashion sense of wearing bright colored calico fabric… everyone had a gimmick.
He also created the most common pirate flag everyone knows today, the black flag with the skull and two swords. That was his design and yet, no one ever remembers that. Unfortunately for Jack, he’s more of a supporting character in his story of betrayal, love, adventure, and a little death but before we get to the main characters, let’s find out why Calico Jack is actually a pretty bad pirate.
Recap
Like almost every other pirate not much is known about John Rackham before he became Calico Jack under the charge of Charles Vane. In case you haven’t read our last pirate article on Charles Vane, here are the pertinent bits.
The King issued a pardon for all pirates in order to reduce their numbers and since he wanted it to be quick there was a deadline. Many pirates agreed, turning themselves into the governors of the colonies while Charles Vane decided to say “Nah” and decided to revolt against the pardon.
Some pirates even joined him but when Blackbeard along with other big-name pirates take the pardon and you don’t, you should probably rethink your stance. Either way one of the pirates that joined Charles Vane was Calico Jack, becoming his quartermaster.
The Betrayal
Charles Vane was seen as this brave, strategic, ‘against the man’ kind of pirate, going as far as taunting Woodes Roger, the Governor of Nassau, when he escaped his ambush. So it became a problem when Vane started displaying cowardice.
After deciding to not attack a large French ship despite the rest of the crew wanting to, Calico Jack led a revolt against Charles Vane. And by that I mean, he requested a vote since pirates were pretty democratic.
Charles Vane lost the vote 16 to 75 and Calico Jack tossed Charles Vane into the sea to live out the remainder of his life. By that I mean he gave him a boat, plenty of supplies, and allowed those loyal to him to accompany him because pirates weren’t always ruthless.
Related Article: Captain Charles Vane: The Lucky Pirate
A New Captain
With Charles Vane no longer captain, Calico Jack was voted to captain in December of 1718. The problem with Captain Jack was his lack of experience, he wasn’t a skilled fighter or a tactician, sure he seemed good with words but you can’t convince an opposing ship to surrender with words.
Either way Captain Calico gained a few small victories attacking smaller ships, possibly building up his little confidence for a big ship.
Finally off the coast of Port Royal he had his chance when he spotted a large Jamaican vessel called the Kingston. Now a good pirate would take his time, wait it out a bit, and make sure there are no witnesses since they were pretty close to the coast. But this is Captain Calico Jack, the man with something to prove!
Surprisingly Jack and his crew were able to take the large vessel pretty easily but the problem was he did it in clear view of all the witnesses, possibly with a huge sign saying “My name is Captain Calico Jack, tell everyone what you saw here.”
Merchants who just lost their goods to Jack and government officials witnessed the whole thing. They then decided to go after Jack and his men as punishment by gathering a large Spanish warship along with a smaller ship to track him down.
A Bad Captain
Now a good pirate might have gone pretty far away knowing they were witnessed committing a crime and knowing that the deadline for the pardon has passed so they faced certain death. How far would you have gone? Otherside of the world? Over towards Africa? Spain? China? How about just a little over 200 miles away or under 400 kilometers?
Because that’s what that fool Jack did, he stole the ship near Port Royal Jamaica and then went to a town in Cuba, that’s like if someone stole your car and then parked it a block away.
So needless to say they were spotted pretty quickly but they were a bit lucky.
Since the Warship was so large and the tide was low it couldn’t pull into the port. Instead, the Spanish Warship blocked the exit and waited till the morning when the tide would be higher to attack the pirates and take back the Kingston.
Escape
In what I can only assume wasn’t Jack's idea, the pirates hid till the middle of the night and then attacked the smaller English ship all stealth-like. When morning hit the Spanish warship moved in on the Kingston shooting at the now empty ship. Meanwhile, just behind them the English ship, now manned by Jack and his crew, sailed away.
Despite living another day, this was still a huge setback for the crew. They lost everything and just barely made it out. They had to rethink their positions and agreed to try to get pardoned. The only problem with this was, that the deadline had passed and who would want to pardon the ex-crewmates of Charles Vane?
That’s when a lightbulb turned on, there might be one person who would gladly pardon them because of their hatred for Charles Vane… Woodes Roger.
A Possible Pardon
The crew headed back to Nassau, the former pirate republic, and begged for a pardon, then they did that thing that people do when they’re desperate and have no backbone… They lied. They told Woodes Roger the only reason they ever went into pirating was because Charles Vane forced them, it’s not the life they wanted, it’s the life forced upon them.
Some historians believed Woodes Roger knew they were lying but because he hated Charles Vane just “oh so very much” he granted the former crew their pardon. Of course, if they were ever to return to pirating they would be put to death.
The crew agreed and swore they would never return to piracy but like most of these stories we know whenever a pirate swears they have at least two fingers crossed behind their back. The difference here is John Rackham at least tried to never become Calico Jack again. He stayed in Nassau and tried to keep on the straight and narrow.
The New Pirate
That is, until one day, while drinking at a tavern he watched a beautiful fiery woman beat the living crap out of a man who was harassing her. Her name was Anne Bonny.
In our next pirate article, we’ll conclude the story of Calico Jack and tell you about the true main characters in his story, Anne Bonny and Mary Read.
