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Leon rarely cries probably. But when he does, he doesn't want other people to see. Exhaustion and sleeplessness just pushes it for him sometimes. He's just being human.

This is set sometime after RE2. And since the remakes never really gave remake scenes of this part of the lore, I made my own spin of the "deal" part and made it... harsher. I imagined Leon tried to visit Sherry as often as he could but couldn't visit more often in later years and kinda lost contact (just my headcanon). But I think he reconnected with Sherry after the events of RE6 and then we get their dynamic in RE9 where he can be a dad to her again.

He's sad in the last panel because he thinks he'll never be free.