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This is kinda sad, but my first was the event Arceus. I have been close though. Level 94 Typhlosion on Crystal, and my current Typhlosion on Soul Silver is 93. Those are the closest I have.
The event Arceus. I've never raised a Pokemon to Lv. 100 in the main series games, rather sadly.
In PMD Darkness, I have a Lv. 100 Charizard, Meganium, Feraligatr, and Lucario, though, don't know if those count.
Going by release dates, Typhlosion on Gold, which is a beast with crazy stats though I never SR'd (let alone hacked) for it.
But the first one I actually caught and raise to that would be one of my three Hoenn titans on Ruby, as I painstakingly went through the E4 dozens of times for the experience.
My FR has teams of individual 100-levels. Tons more (mostly cloned) on Emerald.
Huh, it just occurred to me that I've never actually raised a Pokemon to level 100. The closest I ever got was my Pidgeot in Yellow, which was level 88.
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