With a current total of 25 seasons and Ash currently fighting Leon at the World Championships, the Pokémon animated series has so many memorable moments that it's nearly impossible to count. But alongside the highs, are the lows, and when you've been ten years old for over 25 years, you're inevitably going to make a lot of mistakes!
Ash has shown both great capability and stupidity throughout his journey, the latter seemingly being more memorable than the former. As great as it was to finally see him win a Pokémon league, it was also just as painful to follow the journey that got him there. Ash's career, particularly early on, was marred by bad decisions. Decisions that were so bad that they even played a factor in delaying his dreams of becoming champion.
Leaving Brock & Misty
Brock and Misty are the first true companions that Ash made at the offset of his journey. Serving as friends, mentors and at times even rivals, these two are as iconic as the perpetual child himself. The three of them formed what is perhaps the most cohesive unit the show has ever seen.
Between Brock consistently botching any attempt at romance and Misty's determination, the trio of friends, and subsequently their characters, balanced each other out perfectly. Despite Ash selfishly shooing them away in an attempt to hide his emotions, the conclusion of the original traveling trio's journey is still a heartfelt moment that taught kids around the world that even the best of things must come to an end eventually.
Using Charizard In The Indigo League
Seemingly the most boneheaded mistake ever made in a Pokemon league battle, Ash calls upon Charizard to bail him out of his battle with then-rival Ritchie. Ash knows that this battle is an important stepping stone that he must clear if he hopes to achieve his dreams. Prior to sending Charizard into battle, he reflects on the times that Charizard refused to listen to him.
Whether false hope or ignorance was the deciding factor for Ash, the end result was the same. Instead of strategizing and doing his best, he tried to rely on the sheer power of Charizard to cover for his shortcomings as a trainer. While the two would ultimately end up becoming an iconic duo together, this is a clear example of Ash not learning from his lessons.
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In what is arguably the most selfish moment of his training career, Ash again looks to take the short route due to his shortcomings as a trainer. After being handily defeated by Lieutenant Surge and his Raichu, it was clear that changes needed to be made. Ideally, Ash's approach to training.
Yet once more Ash failed to realize that the bond between a trainer and their Pokémon is what makes them most powerful. Disappointed at his Pikachu's evolutionary form, Ash holds a thunderstone up to Pikachu, contemplating if he should evolve him merely for the sake of obtaining a third gym badge. Thankfully, Ash changes his mind and does things the right way, but it's still clear that his moral ambiguity nearly resulted in forever changing his best friend.
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In the midst of the final battle that occurs in Pokémon The Movie 2000, Ash finds himself quite literally at his wit's end when trying to stop Mewtwo. Overcome with emotion and drained of logic at the sight of such harm being bestowed upon Pokémon, he attempts what is perhaps the most asinine move in anime.
Given his past physical altercations with Pokémon, one would assume that Ash knows better than to try taking one on in a fistfight. Let alone the most powerful being known to man at the time. Yet he proceeds to promptly square up with what is the equivalent of a god. No one ever said you had to be smart in order to catch 'em all.
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Perhaps the only entry here that features Ash making a mistake out of goodwill. His demonstration battle with Misty is as bad as it is laughable. Eagerly wishing to show her that there is an upside to every Pokémon, he foolishly forgets about one of the world's most fundamental mechanics, type matchups.
What ensues is one of the most one-sided beatdowns in the history of the anime. As children around the world screamed at their televisions, begging Ash not to do this to a poor Caterpie, they were helpless in watching him send it into battle against a wild Pidgeotto. While his heart may have been in the right place, his brain was clearly not, and the poor Caterpie suffered the consequences for it.
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Once again proving that he has absolutely zero capacity for learning from past mistakes, Ash once again seeks to rely on the strength of a single Pokémon in order to win a gym battle. Granted, he had the right idea this time by utilizing type matchups, but he still failed to see the obviousness of his errors. And, once again, a Pokémon unnecessarily pays the price for it.
There seems to be a running theme in regard to Ash struggling with electric-type gym leaders, as is the case here with gym leader Elesa. Thinking that Plapitoad's type advantage alone, literally, was enough to overpower her entire roster, he starts the battle with it as the only Pokémon in his party. After Palpitoad succumbs to her Emolga, he's forced to scurry back and retrieve his other team members in order to finish off the battle. Even beginners know better than to try this, which made it excruciating to watch in real time.
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Another incredibly painful running theme within the show is Ash constantly releasing his strongest Pokémon. For a trainer who's been vexed by the idea of power as many times as Ash has, this just doesn't make sense. How does one go from depending on sheer strength in order to save their dreams, to giving it up the second the journey seems "over"? Even worse, it's always the members of his team that made the most impact.
Ash quite literally merged bodies and became one with Greninja, something that would assumably make the duo a lifelong pairing. Between saving the world and winning illustrious battles together, it's hard to believe that Ash would leave him to the company of Zygarde. Hopefully, someday they'll reunite, but that day probably won't come any time soon, unfortunately.
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Ash and his Butterfree are responsible for some of the most heart-wrenching moments in the entire franchise. However, this particular mistake is perhaps the most painful, for many reasons. After being impressed by a Raticate that knows jump kick, Ash seeks to trade his Butterfree away in order to obtain it.
While the morality surrounding the trade itself is highly questionable, the chaos that follows is what's important. Ash's trade proves to be explicitly responsible for endangering the lives of others as he and his friends become trapped on a sinking ship due to unforeseen circumstances. Between trading away a friend and endangering the lives of those around him, it's fair to say that this was not his finest hour.
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In the series pilot, after choosing the whimsical Pikachu to be his starter, he finds himself struggling to command the respect of his newfound companion. After Pikachu refuses to battle a wild Pidgey, things take a turn for the worse when a flock of Spearow begin to chase them and Ash throws a rock at the Pokemon in response.
While his bravery inspires Pikachu to save his life, it comes at the cost of the electric rodent's health. Gravely injured and drained of all energy, Ash scurries off to find the nearest Pokémon center for help, hopefully learning a valuable lesson about picking your battles.
Releasing Charizard
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Undoubtedly the most painful episode of Pokémon is Charizard's Burning Ambition featuring the very same Charizard that Ash so desperately depended on to save his Indigo League dreams! The rule of Pokémon is that those who are stronger than their trainer's skill level, tend not to listen. This heavily implies that Charizard, a fully evolved, fire-breathing dragon, was indeed Ash's most powerful ally.
However, for some reason, Ash sends him away to train. To clarify, he sent the strongest Pokémon that he'd ever possessed up to that point away to get even stronger. The logic here is as baffling as it is laughable. Truly nothing can compare to the ignorance that Ash possessed that day, as it is by and large the most ridiculous decision that he's ever made in the history of the franchise.