Sailor Waddle Dee is named and dressed as such because he used to be part of a gang of Waddle Dee sailors who sailed to different areas on Popstar to steal things. He was often picked on because he wasn't good at stealing things (Because he had a good heart deep down), and his ship sailing skills were mediocre at best. One day, the Waddle Dee crew's ship accidentally crashed on a desert island. The other Waddle Dees blamed Sailor for the incident, and once they fixed the ship, they abandoned him on the island. Eventually, Meta Knight found him uncunconscious, and he took him in. Sailor Waddle Dee was so grateful to Meta Knight for saving him, that he offered to work for him, and he swore that he'd always be loyal to him. He's been a part of Meta Knight's crew ever since.