Edward Kennedy (born 1713) was born in Port Royal to a poor family. Being severely taxed by the King, Edward's family was evicted from their home and all of them murdered except for Edward, still a child. Edward quickly devoted his life to piracy and had a bounty on his head by his adulthood.
Shortly into his adulthood, Edward joined the crew of the Sea Comet, a War Sloop captained by a seasoned pirate. Edward served as cabin boy for several years and eventually lead a mutiny against the captain. The mutiny was a success, and Edward was named captain. The crew was unsuccessful for many years, until one day the ship was confronted by a Navy War Brig. After a half hour of conflict, a chain shot broadside from the Comet brought down the Brig's sails, and the crew surrendered. Edward made the decision to scuttle the Sea Comet with the Navy crew on board. He then took the role as captain of the Warship, painting it in a unique fasion and named it the 'Skysail.'