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It’s more like Damian doesn’t know the full extent of John’s abilities and his Pokémon. I believe he can take one with his full team as of now. Even more so with how many dark type he has. But the step betwen Gym Leader and Elite Four is quite large. Though, things like Mega Evolution, Z moves and all can bridge the gap. :)
No, he's right, it is Ricardo. After rereading the previous chapters, I realized I mixed up some of the names. That should be fixed now—my bad for the mix-up
When he cleared his first dungeon, that was his reward for completing it for the first time.