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Nate/Rosa > Hilda/Hilbert > Pearl > Ruby > Gold > Red
Red comes from a time where Pokemon Training was new. Kanto had just established its Pokemon League, so... it stands to reason that Red became CHAMPION during a time where the meta was not established yet and no one really knew any advanced battling strategies, which is why all of his opponents had sucky teams and moves (e,g, Blue's Rhydon with 3 moves), the idiocy of the AI, etc.
For his time, Red was great, but in today's times, Red would be utterly rekt by any competent trainer, because the opponents Red has faced come from a time where Pokemon training was new and not fully understood. He had it easy mode.
