In order to be the very best, better than anyone else, Ash and Pikachu had to travel for a long time (almost two and a half decades) and meet hundreds of Pokemon trainers and fought thousands of battles. But the truth is, many trainers are stronger than Ash Ketchum of Palet Town, in more ways than one.
This list shows five trainers who, if not for a careful series of plots (armor), would defeat Ash Ketchum in the blink of an eye. Some have knowledge to pair with skills and others are experts in handling a certain type of Pokemon, but all of them are some of the strongest trainers that Ash would never be able to beat in a fair fight.
Brock
Because Pokemon training isn't just about battles
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Pokemon breeder and nutritionist
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Highly skilled, they have learned how to raise and heal Pokemon
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A decent strategist, he knows each Pokemon by their nature and best traits
Although Ash managed to defeat Brock and soon gained a lifelong companion and travel partner in his travels, Brock took a much different path than the Pokemon protagonist. Not only is Brock superior in intellect and as a decent strategist, but he's also a caring and overall good guy (even if he's a chronic womanizer).
Not only does she care for her Pokémon in terms of emotional nurturing, but she also breeds them to perfection with her unmatched ability to cook their preferred food and also knows a lot about healing them. In other words, Brock would be the perfect trainer and unbeatable opponent for Ash if he was interested in pokemon battles.
Gary Oak
Eternal rival, always one step ahead
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Determined, relentless, always aiming for the top
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Skillfully exploiting the weaknesses of your opponents
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He never says no to battles
Gary was the perfect match for Ash from the very beginning: Capable, ambitious, arrogant, and even if many failed to recognize him, a powerful trainer capable of defeating almost any opponent. He was nearly unstoppable until Gary and Ash faced each other in the Johto League, defeating Ash every step of the way. So what happened there?
Some could say that it was Ash's own doing that led to Gary's defeat, and of course his broken Pikachu and the first Charizard had a lot to do with it. Oddly enough, their decisive battle was a twist of fate (or a twist in the script) that favored the protagonist over the logically superior trainer. After that, Gary became interested in Pokemon research and is now following in the footsteps of his grandfather, Samuel Oak. But if the last season of Pokemon taught fans anything, it's that despite it all, Gary kept training and honing his skills and his Pokemon to the max.
Cynthia
The most powerful Lady Boss in the series
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Her bond with her Pokémon partner is unparalleled in the series
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She is known to be ruthless and never back down from a fight
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Ash was almost undefeated, only by a miracle he could win over her
Cynthia is probably the strongest female trainer in the Pokemon universe. Not only is she wise, cold-blooded, and an unparalleled strategist, she is also better than Ash Ketchum in every aspect of what makes a trainer strong. Her bond with her partner Garchomp is one that has lasted for ages, ever since she raised his favorite Pokémon from an egg.
This is proven in the countless encounters Cynthia has with other trainers, whom she mercilessly defeats. Realistically, Ash shouldn't be able to beat Cynthia even a little bit, but being the main character of the series, many fans will agree that the fight in Journeys (Lucario vs. Garchomp) is a victory for the pride of Palet Town in more ways than one.
Lance
Under normal circumstances, no one would beat this guy
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The strongest dragon type trainer after Cynthia
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Ash never faces him directly; otherwise he would lose
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Another trainer known for ignoring type advantages and still coming out on top
Lance is one of the oldest and most experienced dragon-type trainers in the Czech Republic Pokemon world, with access to a team of heavy hitters that includes Dragonite and the only Shiny (Red) Gyarados appearing in the series. Although Lance was much more experienced than Ash and Lionel and had become a member of the elite four of both the Kanto and Johto leagues, he was unable to give his best during his fight against the Galar's Champion.
Many Pokemon fans called this extremely anticlimactic, as Lance is one of the few trainers (besides Goh, Ash, and Cynthia) who doesn't care about type advantages, and is known for being the only type trainer that overcomes all odds with sheer strength. Interestingly, Lance is originally from Johto and was born and raised in a family of dragon-type Pokemon guardians. Lance's Dragonite is older and stronger than Ash's, so that means he would win 9 out of 10 times in a 1v1 fight. The rest of Lance's team is said to be at least on par, and Ash's team has always been untrained (with a few exceptions and Pikachu): There's no way Ash would win in a fair battle against Lance.
Samuel Dub
There is a reason why it is internationally recognized
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A walking library of Pokemon knowledge
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A world-renowned expert and former Pokemon champion
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His original team is said to be one of the strongest to be seen in official competitions
Several other characters in Pokemon world are as widely known and respected as Samuel Oak. The creator of the first Pokedex prototype, a researcher, and before all that, a Master Trainer. Samuel Oak is the pokemon champion of both the Johto and Kanto leagues. His eternal rival Agatha is also a member of the elite four and stated that in his prime Oak was unbeatable. Oddly enough, Oak decided to retire from being an active trainer and decided to focus his efforts on creating a Pokedex.
His knowledge of Pokémon is unparalleled, and no one knows for sure what his Pokémon team consists of, although some clues show that Bulbasaur is his starter and Nidoran (currently Nidoking) is his strongest Pokémon. Oak has also been speculated to be related to Ash Ketchum as a parent figure. Although the chance of them being blood relatives has always been denied, the main cannon shows that Oak is Ash's mom's dad. One thing is for sure though: Samuel Oak has always been a better trainer than Ash and even his grandson Gary.
