In 1718, Rackam served as quartermaster on Charles Vane's pirate ship. One day Vane's ship encountered a French man-of-war and he decided to retreat from the battle. Many of the crew felt differently on this matter, including Rackam. The next day, Rackam and crew confronted Vane and stated he was a coward. The crew elected Calico Jack as the new captain. And within the day, Calico Jack was able to plunder several small vessels.

In May 1719 Rackam sailed to the Bahamas for a pardon and settled down there soon after. While in a local tavern he met Anne Bonny whom he soon started to court. Once their money began to run out, Rackam returned to piracy and convinced Anne to come with him, which she did, only disguised as a man. He again went back to plundering his standard small local merchants in the Caribbean. On one of the vessels was Mary Read who would also join Rackam's crew without anyone knowing (yet) she was a women.

Governor Rogers sent Captain Barret and two sloops with 45 men out to find Rackam. They caught up with Calico Jack. Barret ordered him to surrender. The nighttime battle did not last too long though. When Barret's crew boarded William, Calico Jack's ship, only Anne Bonny and Mary Read fought the attackers while the rest of the pirates, including Rackam, simply surrendered without a fight.

On November 16, 1720, Rackam and 11 of his male crewmen were convicted and sentenced to death (the two women were tried later.)

Rackam was able to see his lover Anne Bonny once before his execution and she stated to him "that she was sorry to see him there, but if he had fought like a man, he need not have been hanged like a dog." On November 19, Rackam and his crewmen were hung.

Heave to, ye swabs, and get yerselves back to the Main Deck!

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