Pokemon Anime Can't Be Original....right!? No, it's not okay. Ash hasn't won not ONE "official" Poke'mon League. The Orange League Islands was a filler season and the concept of orange Islands didn't even come from the games. After so many years, Ash's destiny is be a total Poke'mon failure.

Besides Ash not winning any of the Leagues, there's far more problems in the anime which prevent me from watching it anymore.

- The "OH A NEW REGION, I'M GOING TO START FROM SCRATCH...AGAIN!" every new generation.

- Ash not owning a legendary.

Not to mention you can make so many stories revolving around the fact that he owns one.

For example: Ash now owning a legendary has become overconfident and solely relies on his legendary to win. He becomes ignored towards his other pokemon in training. After relying so much on the legendary, when it's finally defeated he'll have to switch to his other pokemon who haven't been properly trained/ used very often thus resulting to his defeat in some type of plot which leads up to to his realization that he lately has been a terrible trainer....etc.etc. some moral at the end. It's gives off more depth and character development and it's a good example of how hes still "learning".
- Most secondary characters or rivals disappearing from existence or barely appearing at all.
What happened to Butch and Cassidy? Ash clone Ritchie? Tyson?Paul? and all those "once in a while" friends.

However Gary did have a nice comeback at the end of advanced generation and made a few appearances in DP.

- More character development. Give ash a life besides being a tool and trying to be the best trainer. What happened to his friends in EVERY region? It's OFTEN implied there's something going on. What happened to his long lost father? Did Ash mother cheated after Ash father gone? Did Professor Oak hook up Ash mother after Ash left Kanto?

If anything the series is about as repetitive as the game themselves but the games argument is for a different discussion.