Did I say think I meant hope. 

He's been at this since show 1, probably should just retire :p

Does he at least win the girl? That's more important.

Wait, did people seriously believed that Ash would win?

LOL, i mean none of the characters didn't had any serious development during the past 10 years. The anime is only for keeping the franchise and the games around.

Ash has lost like 6 or 7 leagues and instead of taking some time alone and think ''what the hell am i doing with my life'' he just smiles like nothing happened. It would be okay if it was only for one time but the lesson here should be ''ash lost a number of times but at long last, after many hardships, he became a champion''. But noooooo, stupid writers don't care about that.

BAHAHAHAHAHAHAHAHAHA!!!
Oh well, back to an incompetent 10 year old it is for next season
Pokemon, Pokemon never changes.

Well.... off to Alola (hangs head in misery)

Wait why are you discounting Sinnoh? How was that an anomaly? 

Ah well I wouldn't get your hopes up especially after today.

After today? No chance in hell! They clearly don't give a shit about changing up the status quo or giving the fans what they want.

Uh yeah, where have you been?

Compare the Ash from the Kanto series to the current Kalos Ash. There's clearly been development as he's actually mature strong and strategic now, exactly how he should be with all the experience he has now.

And here a lot of us had hope that he would win the whole thing and we'd see something big happen with the anime... but alas....
Ash will keep losing Pokemon Leages for each and every single generation to come, starting over at a a new region, rinse and repeat until they stop making Pokemon games forever!
......He's never going to win. :(

Look at your image in the OP:  16, 8, 8, 4, 8.  Sinnoh is the only time he placed above 8 and is bookended by two 8s.  That's why I call it anomalous, cause it represents an unusual step forward that didn't go anywhere since he went right back in the next season.  

Also just occurred to me Ash will probably win Alola just like he did the Orange league, seeing as how Alola is similarly unusual.  And then they will either have that be a spring board for winning a "big league" OR do what they did with the Orange League and make dead certain to belittle the accomplishment and have him probably finish 2nd again.

Ah, well then you can't say XY is a step forward for the first time until we see how Ash performs in the SM series. They could very well pull another BW.

After today I definitely would not expect Ash to win anything no matter how much sense it makes for him to. The writers have clearly shown that they give a rattata's ass about logic.