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The most depressing story in Pokemon is from a manga nobody read

Blackjack Gabbiani

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I posit to you that the absolute saddest story this franchise has ever told is Hill of the Lone Star Tree from Magical Pokemon Journey. In it, we meet a Quagsire who's very old and clearly suffering from dementia. He can barely remember who he is, but he remembers a promise he made to a friend a long time ago, and he and his trainer are trying to fulfil it.

In his youth, the Quagsire had been friends with Mandy the Charmander, and they would play on a hill with a distinctive star-shaped tree. They had promised to meet again there someday. But Quagsire can't remember where the hill is.

They meet a girl who says she knows where the tree is, that it was very important to her family's Charmander--the very same Mandy! But...when they get there, they find Mandy's grave. The girl says that Mandy had always said that someone important to her was supposed to meet her there, but he never showed up.

Quagsire starts sobbing his beady little eyes out and sputtering about their promise. Just then, a spirit manifests before him and calls him by name (turns out his given name is Cyrus). Mandy's spirit seems to welcome him and guide him to the afterlife, and they vanish together.

However, turns out that this was just his spirit and he was somehow astral projecting because he's too old to travel. The real Quagsire is still alive...and has already completely forgotten everything that happened. The entire journey, including reuniting with Mandy's spirit, was utterly forgotten, and he's left still wanting to find her.

There are a lot of woefully sad stories in this franchise but this is the only one I can't even describe without bursting into tears. Oh yeah and this is the story that Viz ended their English run of this series on! This is the last impression most English speaking fans ever got of what had been mostly a lighthearted slice of life.
 
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