PokéBase - Pokémon Q&A
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I've never watched the anime in any sort of meaningful depth. It's possible there is no objective answer to this question, so if this is flagged or closed forgive me, and I don't mind. I have little to no background on the topic, but a friend piqued my curiosity. I simply wondered if there was any match, or select few matches across his journey, where there is common or sensibly reasoned consensus that they were the clear-cut easiest Badges he earned.

If there is actually a way to answer, please provide evidence as to how they were. If it's not, I figured it couldn't hurt to ask. Essentially, this is an anime question from a gamer's perspective.

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Wattson was definitely the easiest from what I've seen
i just started season 3, but from what I watched probably any of the orange island gyms.

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While they were accompanied by battles that he (typically) lost, he earned most of his Kanto badges by being given them. I’m not sure if being handed a badge without winning the battle would qualify, but that was fairly common through his Kanto adventure.
EDIT: forgot to show my work earlier, sorry. The only badge he won fair and square (like the rest of us) in Kanto was the Thunder Badge.

https://www.cbr.com/pokemon-ash-kanto-badges-won-by-battle/

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