|This article contains information that only comes from the anime, not the manga.|
For more information on this, see Filler Episodes.
A few years ago a fight, or rather a so-called “duel”, took place between the rising star in the naval sky “50 Pistol Daddy” Masterson and a commander of Shanks’ pirate gang, Usopp’s father Yasopp. Nothing is known about how the fight went down. All that is known is that the hitherto undefeated Daddy was badly hit, while his opponent was only grazed. The winner was Yasopp.
Although the 50-gun Marine captain eventually asked for the coup de grace, Shanks’ fellow soldier still let him go, due to the fact that he, like himself, was the father of a young child and therefore could not simply die. He only learned this after seeing a Carol Masterson trailer.