It's ok for Ash to lose most leagues… but for him to not win a single league, ever, it's like what's the point of even watching?

See it like this. Rocky is a nice movie with a similar structure. An average guy wants to win a tournament against arguably much stronger people. He trains a lot, makes sacrifices, and is ultimately barely victorious.

Now, Pokémon is arguably the same thing, and the hero's journey is not only common in shonen animes, it's almost the norm. HOWEVER, although a journey has ups and downs, it also PROGRESSES somewhere.

Pokémon not only has been doing this for twenty years, far beyond what most could be asked to care for, but his hero doesn't progress. I don't only mean that he doesn't age, that's almost trivial, but he doesn't learn anything, he doesn"t become a better trainer, he still makes rooky mistakes, he is still surprised that the team rocket is after him and he will still try to electrocute a fucking rock pokemon.

That's not being an underdog, that's being retarded. The reason why is obvious: as long as TV Tokyo can milk that anime, ash will be trapped in a constant cycle of regression of, in a way, endless filler episodes.

Want to watch some good pokémon stories? Pokemon origins is great. Most of the pokémon mangas aren't bad either, strangely enough. All that becore, although the story isn't necessarily great, at least it goes somewhere. Blueballing your audiance asking for the sweet release of death for 20 years isn't a good idea