As far as he cares, Willis' life began when he was twelve he was selling cooked clams for a local restaurant on the port, he met Pirate Captain Davis. Captain Davis was looking for more crew members after losing half of his crew due to a storm. Seeing it as an opportunity to leave Alliria, Willis dropped what he was doing and ran to the captain and offered to be one of his crew members. Captain Davis laughed and moved on, however, Willis began to follow him from the shadows and discovered that Captain Davis had his compass stolen from him by a rival pirate captain, a pirate named Blindbeard who just docked. Willis heard of Captain Davis intention to kill Blindbeard he managed to slip away, find Blindbeard who was in a Tavern and was really drunk and unruly.

Willis was about to pickpocket the compass but all of a sudden, Blindbeard started a brawl with the other people in the Tavern. Willis stayed hidden as chairs and people were thrown around until he saw the compass fall out of Blindbeards pocket. Willis took the opportunity of the chaos and grab the compass and went back to Davis and gave him the compass. This impressed Davis and he took Willis under his wing saying that “he reminds him of his son,” and he spent the next four years at sea as a pirate on the ship: Sea Dog.

Willis' role as a pirate was mostly him fishing and cooking for hungry crewmembers, assisting the ship doctor with common ailments, such as scurvy, constipation, boils, or splinters, for injured pirates and playing the flute which the first mate taught Willis to entertain them. Willis found both fishing and playing the flute fun and didn't mind the work. He excelled as a crewmember, never complaining and being the first person waking up and fulfilling his duty which earned the Captain's respect. As a reward for his hard work, Willis was taught to read by Captain Davis and was taught basic navigation skills, potion making, and grenade making.

Captain Davis also taught Willis his personal code of morals saying: "A mans gotta have a code! Lest he be a monster!"To defend himself in case, the pirates get attacked, Willis was given two swords and was taught proper swordplay by Captain Davis who was an experienced dual-wielding swordsman. In addition, the first mate briefly taught Willis how to use a crossbow to provide backup in case the main crossbowman went down. Willis proved to be a talented fighter killing his first man at 14 during a Pirate raid.

When Willis was 16, Captain Davis and the crew were caught in a huge storm and struggled to maintain the course. Willis tried to help the crew but the violent winds plus the thunder and lightning caused the ship to sink leaving Willis as the presumed sole survivor washed up on an island somewhere, during his time on that island, Willis began to reflect on the code of morals that Captain Davis taught him and vowed to follow them if he gets rescued. By luck, Willis was rescued by a merchant ship that was passing by a week later.

Willis left his Pirate life behind and began looking for more work. While staying at an inn, Willis saw on the notice board an offer to join a mercenary company. With the skills he acquired from pirating, Willis began to do mercenary work. He joined the company and found some success, even falling in love with a woman named Molly whom he had a relationship with. However Willis eventually left them as quickly as the company did things that were against his code combined with the fact that there was tension between he and Molly due to Willisʼ unwillingness to marry, he decided to go solo.