Pokémon's Ash Ketchum is no stranger to failure, more like best friends with it. In his quest to be the very best, like no one ever was, Ash stumbles more often than he stays upright. Though his skill as a trainer has improved tremendously, his track record still leaves much to be desired. While each of his journeys through a particular region is capped off by a Pokémon League tournament, for a long time the question was never "will he win this time?" but "how will he lose this time?"
Granted, winning the Pokémon League is a monumental challenge. A trainer must collect eight Gym badges, then triumph over a 64-person tournament full of trainers who are just as strong or far stronger. However, the gripe with Ash is that he's spent the majority of his Pokémon career not even coming particularly close to winning and managing to lose in either heartbreaking or frustrating fashion. Let's look back at each of Ash's six Pokémon League eliminations from the most tolerable to the most painful.
The Johto League: Ash's Best Just Isn't Enough
Ash's performance in the Silver Conference is a rare example of him deserving to take a loss with his head held high. Reaching the Top Eight in his second attempt at a Pokémon League tournament, Ash's trademark cleverness in battle helped him defeat his longtime rival, Gary Oak. Even Ash's final battle -- where he is eliminated by his new friend Harrison -- is filled with flashes of signature Ash moments, from Pikachu grabbing Kecleon's tongue to Totodile dancing with Sneasel's claw in its mouth.
Meanwhile, Ash's Pokémon showcased their skill against Harrison's powerful lineup, but it all came down to Charizard vs. Blaziken. Unfortunately, Ash was out-clever'd when Blaziken withstood Charizard's Seismic Toss by using a Flamethrower on the ground to slow their descent and soften the impact. Though Charizard was defeated, Ash's Pokémon gave it their all and there's no shame in losing against such a strong opponent. Harrison just managed to pull out the right move at the right time in a match that could have gone either way.
The Kalos League: Ash Narrowly Misses His First Championship
Ash seemed destined to win the Lumiose Conference after he blazed through the competition prior to his matchup with Alain in the Finals. While it was disappointing to see Ash finally reach the final round only to lose, it doesn't take away from the performance he put on during the dramatic showdown. Alain was no pushover, wielding two Pseudo-Legendary Pokémon (both of whom were singlehandedly defeated by Pikachu), and his Bisharp was spamming a one-hit K.O. attack that bordered on unfair.
The final bout between Ash-Greninja and Mega Charizard X is one of the greatest clashes in the Pokémon anime. Unfortunately, despite its Type advantage, Ash-Greninja was unable to bring down Alain's Charizard, the Mega Evolved Pokémon simply too strong. It's tough to be too hard on Ash for coming out the loser in a spectacular, very close battle against an established adversary in Alain who was on a compelling journey of his own. Some might say "if you're not first, you're last," but taking second place in a massive tournament of powerful trainers is no small feat, and it's closer to his dream than Ash had ever been.
The Hoenn League: Pikachu Somehow Couldn't Beat a Meowth in Boots
Let the eye-rolling begin, as the remainder of Ash's Pokémon League eliminations are as irritating as they are confounding. The idea that Ash's iconic Hoenn adventures were ended at the paws of a cosplaying Meowth is almost offensively anticlimactic. Meowth are not known for being powerful Pokémon by any means, but to be fair, neither are Pikachu. Still, this unusual Meowth belonging to Tyson -- the trainer who would defeat Ash and go on to win the whole Ever Grande Conference -- is a bit too gimmicky with its cowboy boots and feather cap.
Tyson was a powerful trainer, though, as his Hariyama and Metagross each defeated two of Ash's Pokémon. Spending most of the battle at a numbers disadvantage, Ash manages to make things close at the end before Pikachu falls against Meowth. Finishing in the Top Eight for his second consecutive tournament, it was salt in the wound that Ash's progress was stagnated by such a strange choice for what was essentially the final boss of the entire Hoenn saga. And come on, it's a Meowth.
The Sinnoh League: Ash Gets Annihilated by Action Replay Man
Ash's performance in the Lily of the Valley Conference is one for the history books for both good reasons and bad. Fresh off a victory over his greatest rival, Ash reaches the semi-finals for the first time -- only for his next opponent to be Pokémon's writing staff. Tobias was simply not fair. It's said he defeated every Gym in Sinnoh (and every opponent in the tournament) using only his Darkrai, a Mythical, Legendary Pokémon. Darkrai would go on to mow down Ash's first three Pokémon before finally being defeated by Sceptile.
While Ash's accomplishment has him believing the worst is over, Tobias is aghast that he must use a second Pokémon and sends out a Latios. Tobias' second Legendary Pokémon makes quick work of Ash's next two Pokémon before fighting Pikachu to a draw, eliminating Ash. After defeating Paul, the series realized Ash was too strong and decided to feed him into a meat grinder named Tobias to prevent him from winning the whole tournament as he should have. A tough loss is easy enough to accept, but that Ash defeated two Legendary Pokémon and still lost by a landslide is just bananas.
The Unova League: Ash's Opponent Didn't Even Bring Enough Pokémon
Ash was never going to win the Vertress Conference, as his Unova adventure was a tremendous backslide in his skill as a trainer. At least his battle against Tobias was an expected loss, because Ash absolutely should have won his battle against Cameron. To put it bluntly, Cameron is a joke of a trainer who arrives for his full battle against Ash with only five Pokémon, somehow blissfully unaware that a full battle requires six.
The six-on-five advantage is quickly squandered when Cameron's Hydreigon wipes the floor with Ash's first two Pokémon. With the remainder of Ash's team weak and unevolved, Cameron takes control of the battle once his Riolu evolves into Lucario. After a tough-ish battle, Pikachu is defeated, marking the first time Ash has ever done worse in a tournament than he did in the previous one, only making it to the Top Eight this time. The fact that he backslid while being defeated by a less-than-intelligent trainer who didn't even bring a full team is… a lot.
The Kanto League: Ash Is Eliminated by Forfeit
It makes perfect sense that Ash's worst Pokémon League showing would be his first attempt, way back at the Indigo League. While cracking the Top 16 on his first try is impressive, it's completely undone by the sheer absurdity of his matchup against his friend, Richie. First off, Ash almost doesn't even show up to the match because of a Team Rocket encounter. By the time he arrives, his Pidgeotto is so exhausted by Team Rocket that Ash has no choice but to use Charizard for his final Pokémon.
No one was less a fan of Kanto Ash than this Charizard, and its refusal to battle against Richie's Pikachu forces Ash to forfeit the match. This loss is the encapsulation of everything he did wrong during his Kanto campaign, and the experience he missed out on by accepting several charity badges reflects the skill of a trainer whom his Charizard refuses to respect. Mercifully, Ash had nowhere to go but up from here, and he's certainly redeemed himself both with his unbreakable bond with Charizard and his (eventual) Pokémon League victory in Alola.
