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This would explain so much actually. Why else would he let a 14 year old just leave?
as I'm writing Mazzaroth, and important to keep in mind: A and B are older than L to me, I'm just thinking... What if Roger became non confrontational and passive after A's death? What if he used to be quite strict in the past, but then he felt responsible that a kid he had in care died and thought that if he had been more lenient, that wouldn't have happened? I know how the majority of the fandom views Roger, Watari and the Wammy's, that is quite different from my own (made a 8k words post about that, so I can't really summarise it). But I just want a serious conversation about these characters, without people jumping immediately to the extreme (the death note fandom does it so often, it's actually headache inducing) and say that they are basically monsters devoid of any human emotion. In my headcanons about A, I also imagine that he first tried to escape, before B (and others, Roger and Watari included) managed to find him and bring him back, so when Mello decided to leave the Wammy's, Roger felt like he couldn't impose his authority, because... What if he reacted like A?