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Kanto and Johto Ash are by far the only times where the character has been anywhere remotely interesting. He was learning, he still had the generic traits that define him today like the excessive enthusiasm and willingness to help but he had other interesting traits like his cockyness and hotheadness. No, I'm not saying he should be the same character forever, but Ash doesn't develop anymore. The loss in the Kanto league taught him humility (plus, it was uncommon for a Shounen hero to fail) and in the orange islands his character arc with Charizard ended. Then in Johto he was a lot calmer but still retained some interesting traits, and then his rivalry with Gary was concluded in a great way.
The point is that they do NOTHING interesting with the character anymore (besides perhaps his rivalry with Paul in DP). He learns NOTHING from his losses. What did these last few league losses teach him? Nothing.
Even his Pokemon seem to have no personality anymore, besides Hawlucha. Where's the bonding phase that Ash had to go through with some Pokemon? Now they love him out of the get-go.
You Ashnime fags keep saying that XY is the best season yet, but it's not. It's predictable and repetitive, and it doesn't have the excuse that the first two seasons have.
Also his original outfit is still the best.
No, I'm not nostalgiafaggotring, look at it from an objective viewpoint and you'll see the first two seasons are the only times the anime gets anywhere close to decent in regards to characterization and character development (because, let's face it, the plot is shit no matter which season).
But hey, at least you got your flashy fights, right?