When he was young, Penguin never thought he'd turn to piracy. His first encounter with pirates left him traumatised and orphaned, with a foster mother too busy grieving the loss of her husband in the same attack to remember how to raise two wilful boys, and a younger brother in all but blood with a penchant for getting himself into trouble.
Naturally, Penguin taught himself to fight - to be strong - so he could protect Shachi if another attack happened, or even better defeat the pirates before they could do any more damage. It even worked, to a degree, for the next several years, into his adolescence. Most pirates saw no reason to trouble the poor island, and those that did used them for trade rather than target practice, so Penguin kept what was left of his family safe.
That changed the day he met Bepo, a monster that spoke like them but was too close to their home for comfort. A kind hearted monster that he later learnt let him and Shachi win, because he didn't want to hurt them. That encounter also led to his meeting with his captain, then sick and barely into his own adolescent, who still had the strength to defeat him without any effort at all.
Even Penguin couldn't say why he made the decision that night to follow the boy - he called it interest, but it was far more than interest that could pull him from the place where he'd grown up and become the very thing he hated with all his being. A pirate.
It was a rocky start. Law, already cemented in his lifestyle as a pirate, didn't understand how to teach two older adolescents to be pirates, and secrets and painful pasts kept close to their chests gave room for misunderstandings and arguments as they pressed the wrong buttons. But somehow, Penguin persevered in his new life, helped in no small part by Shachi's presence, and grew used to being the wrong side of the law. He learnt how to stay unnoticed when necessary, and how to fight for his life when it was the only choice he had.
He learnt to love life again.
Now well into his adulthood, his family has changed somewhat. Shachi will be his younger brother forever and always, but now he has more - Law and Bepo chief amongst those numbers but other nakama cemented in his heart almost as much - and he'll do anything to keep them safe and sound.
- Penguin is a fandragon of the One Piece character Penguin
- Very little information has been canonically released about this character, so almost everything listed here is headcanon or speculation only