A musician by profession and vocation, Jesse was one of the most skillful swordsmen pirates that the 7 Seas had ever seen at the end of the Golden Age of Pirates.
Orphaned when he was only 16 years old, Rackham decided to move to Jamaica where he learned to earn a living playing percussion and lyre on the street. One day, a robust young man with a straight nose, piercing eyes like an eagle and a long red beard, passed by the street. It turned out to be a Berber pirate who went by the nickname Red Beard. When Red Beard saw Jesse's skill with drumsticks, he decided to recruit him to join him aboard his pirate ship. There, he taught Rackham how to skillfully use a sword and other weapons. Each time the pirates conquered a new loot, Jesse was the person in charge of music for the celebration. Also, under Jesse's direction, 2 ships sent by the same Vatican pope were stolen with precious stones and valuable merchandise.
Once, Redbeard decided to travel to Boston, Massachusetts. There, Jesse met a young man named Jheyk in a tavern. They quickly developed a close friendship. In fact, they spent so much time together they felt like brothers. Jesse also began dedicating more of his time to music. When Jheyk's mother died, Jesse swore to his best friend Jheyk that he would not rest until his revenge was over. Becoming his boatswain, the pair were among the most feared pirates of their time, and had a reputation for being ruthless and cold hearted. Later, Red Beard recruited them as musicians in his pirate crew. Together, they vowed that they would not be at peace until they took revenge on Black Jack and seized the Jolly Roger.