Doesn't matter. His goal isn't to win the pokémon league. Its simply to travel every region.

I thought his goal was to become a Pokemon Master.

I hope so, this would mean that from the net season of the Anime we wouldn't see Ash anymore since he would have reached his goal of becoming "Master of Pokémon". Also from the japanese trailer that released last week for Sun/Moon it seems like the game will focus on the journey of the trainer with Hau and Lillie, so the anime might just want to focus on them aswell ! I say let the derp win so we can get rid of him ! Also Ash should've won in Sinnoh when he had the opportunity, His team was certainly capable of defeating the All Leggendary team of the dude...

Wait, he is trying to win the league for 20 years now? How the fuck didn't he got any bit older.

I stopped watching YEARS ago, but he used to make very stupid choices. Not his fault though, I guess Nintendo needs him to reset his pokemon after each league so they can promote new ones.

The only problem I have now, is that he tries to win with only his Kalos team. I like when he brings back other Pokémon to make strategic choices like in Johto or Sinnoh. I remember during the Johto League when they tanken about how they needed to switch up their teams every match because they had to let the Pokémon rest, that never came up during other Leagues.
But overall, it does feel like he could take home the victory, animation, story and character has really evolved in XYZ. Even if he loses to Alain, I wouldn't be mad, Alain is legit and awesome.

God I hope he wins. XY has been so freaking good. I cannot believe how much fanboying ive done with this series. Sinnoh killed me a little. It went on for so long and the last part of it was so damn good. And it gave me hope for BW and it started off great and turned to poop. XY has been amazing since Episode 1.

And the music is so good!

https://www.youtube.com/watch?v=w8E-zxvtSTQ

I haven't followed the XY series because I can't stand Ash after BW but I really enjoyed the Japanese opening called Mega Volt!

Huh? That doesn't reveal anything more than what I covered in the OP.

Exactly!

Not exactly! Winning a League (not even Champion League a.k.a. Elite 4 + Champion) =/= Pokemon Master. He can win this league, hell he can even become Champion, and still go to Kalos. Also, the Ash in BW and the Ash in XY are two vastly different characters. He's actually fun to watch now so I highly recommend you give the XY series a try.

The same way Spongebob, the Simpsons, etc. haven't aged, it's just one of those timeless shows.

Ash has made exactly 0 stupid choices in the XY series, so that shows they can reset his Pokemon without resetting his intelligence and maturity.

His Kalos team is OP though, I mean it's already done way better than any team Ash ever had before. I would be mad if he loses, because it defys logic that with 20 years of experience, having seen every known Pokemon and after having fought in thousands of battles, he still can't win a single league even with an OP team and him playing at his best.

The bigger question is, when will Pikachu evolve?!?!?1