Calico Rackham Jack had mediocre accomplishments as a pirate. His fame comes from the fact that two most famous woman pirates, Anne Bonny and Mary Read sailed under his flag.
Calico Jack got nickname Calico, because he was always wearing lousy striped calico pants. (Calico is clothing material that was made in India in 18 th century. It was cheap and had "unfinished" look.)
Calico Jack Rackham never had enough manpower to attack heavily protected treasure ships. He preferred to use a small sloop and attack fishing vessels and local merchants.
In 1718, Jack Rackham was quartermaster on Charles Vane's ship. On November 23 rd, they encountered a French man-of-war. After realizing that it was not a commercial ship as they first though, Vane decided not to try to board the warship. His crew disagreed and on the following day Calico Rackham Jack was elected as a new captain. Charles Vane and the part of crew that supported him were left in a small sloop.
With his new ship, Calico Rackham Jack captured several small vessels. His share of plundered gold was not big, but he decided to retire for a time being. In 1719, he returned to the New Providence and received a King's Pardon from governor Woodes Rogers.
In the New Providence, Rackham met and fell in love with Anne Bonny. Her husband, James Bonny, in several occasions even threatened Calico. However, at the end Anne decided to leave her husband and ran away with Rackham.
Jack's money was running out, so in August 1719, he stole sloop named the William and returned to piracy. He cruised between Bermuda and Hispaniola and then sailed to Cuba. Again, he only attacked smaller vessels and mostly local craft.
During one occasion, Rackham captured en English ship, and forced several captured sailors into service. One of them was Mary Read.
Calico Jack Rackham and the most of his crew were captured in October 1720, near western coast of the Jamaica. Ship was anchored and crew unprepared, because the day before, they captured Spanish commercial ship and were celebrating all night. According to testimonies, only Mary and Anne resisted. Calico was apparently too drunk to command and even defend himself.
Captain Calico Jack Rackham would certainly be forgotten quickly, if during his trial for piracy, background of two woman pirates were not revealed. Anne and Mary were more than just woman pirates. They broke society's strict rules and escaped traditional restrictions. However, the names of Calico Jack Rackham, Anne Bonny and Mary Read, spread quickly throughout Europe and the America. They became legends, although they were just a minor nuisance.
Calico Jack and his crew were found guilty, for crime of piracy. Anne and Mary were reprieved, when it was discovered that they were both pregnant. With the rest of his crew, Jack was hanged.