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I'm not seeing much difference other than the Subway one having a tie and the Warden one having some pink symbol. And the clothes under the jacket I guess.
I'll just randomly pick Pearl Clan Warden Ingo.
At the risk of being labeled a heretic, Champion Wallace. God, his R/S outfit looks so much better with a cape. And at least to me he was way more difficult than Steven due to his tanky monster of a Milotic as well as Whiscash.
Ahhh, shoot, both involve not respecting a Pokémon's will. I guess I'll go with evolving against their will though, since they'll be in a better position to defend themselves regardless.
Get jump-scared by a Haunter or by a Kantonian Mr. Mime?