Ozzy was a pirate born in Wales, who defected from the army when he was 22 years old. Along with a small group of ex-soldiers, Ozzy took control of a small merchant ship, which signaled the beginning of his life as a pirate. He then spent 5 months as a captain, and shortly later joined the crew of the Royal Fortune commanded by the dreaded Captain Bartolomew Roberts. Ozzy impressive fighting ability and his skills as a sailor led him to become Countermaster.
Later, when Captain Roberts died in combat, Ozzy managed to escape from the ship and arrived in Nassau Island where he met the infamous Captain “Calico Jack.” Ozzy and Captain Calico Jack sailed together for awhile until Ozzy met Long John Silver, who claimed to know the location of William's lost treasure Kidd. Together, they embarked to recover the treasure together. However, when they found the treasure, Silver betrayed Ozzy leaving him alone on a desert island. Later, Ozzy was able to escape from the island and headed to Tortuga where he met a young and ambitious Captain Black Jack and joined his crew.