PokéBase - Pokémon Q&A
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Best answer

He's never beaten a pokemon league. Granted, he did win at the Orange Islands, as well as clearing the battle frontier. (with the offer of becoming a frontier brain himself.) He doesn't win them because they can't easily continue and keep making money off of the series.

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In other words, he never wins because he sucks
That is not what DT is saying. It's the old, if someone wins every time, then it gets boring because it becomes predictable. And besides, he lost to a guy using legendaries.
Who used legends?
Tobias
Ash has never won a real league, his closest was the Kalos league in the XYZ series. He came 2nd as he lost to Allan in the finals due to his amazing Charizard. In my opinion he should have won that battle since he has never won a Pokemon League before as a very good pokemon trainer, soon coming master.
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He didnt won it yet. He even went to that stadium. if watch pokemon black & white every sunday you could catch up what going on and watch is has won the anime or not

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