Ash's Biggest Mistake

Biggest mistake is force-feeding weaksauce to Pikachu after every generation.

His Pikachu can go head to head with LEGENDARIES. New Region, oh dear, he gets taken down by a starter pokemon.

Edit - And eating big bowls of stupid for breakfast, when he returns home after each journey. Drinking nothing but liquid luck during that time does offset this, somewhat, though.
 
I would say his biggests mistakes are when he battles and he uses a type disadvantage pokemon.
Let's say he's going against Donphan. And he sends out Pikachu against it. He should know that Electric isn't effective at all against ground types. And then at the end, he seems shocked that he lost.
 
Dude. The dumbest thing he ever did was that he slept late BEFORE the day when he would get his first Pokémon.

Absolutely correct. Ash was irresponsible. I'm not saying that the Kanto starters would be much stronger than Pikachu, but if Ash woke up on time, he would've become a much stronger trainer to begin with. Team Rocket wouldn't stand a chance against Ash if he'd chosen a proper starter.

His biggest mistake was not growing a day older in 6 something seasons.

Also true. I actually think, in every season, he grows younger. Besides that, Ash never learned anything, imo.
 
Just one I would like to point out is going into Nimbasa Gym with just Palpitoad. Which now I see has been said in the first post. Lol sorry bout that. Another mistake I would point out is he using Pikachu and Tailow in Rustboro Gym. Although he tried to teach Pikachu Iron Tail.
 
I would say that his biggest mistake is giving out his pokemon... Butterfree, Charizard, Pidgeot, Primeape, and many others... at some point he almost let Pikachu go!!
 
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