Ash Ketchum has met many Pokémon League Champions over the course of the Pokémon anime. He even became one himself at the end of the Pokémon anime's 7th iteration, after winning the Alola Pokémon League. Ash's dream since he started his Pokémon journey has been to become a Pokémon Master, and learning from regional Pokémon Champions along the way has been a big part of his growth as a trainer. This makes all his Pokémon Champion interactions incredibly significant.
Each new generation of the Pokémon anime saw Ash journey to the newest Pokémon region to obtain all eight Pokémon Gym badges (or the equivalent, as was the case in Alola), and eventually, take part in that region's Pokémon League. The only notable exception to this rule has been the latest iteration of the Pokémon anime, Pokémon Journeys: The Series, and its successors, Master Journeys and Ultimate Journeys. As Ash fought tooth and nail for each of his Pokémon Gym badges, his journeys would sometimes allow him to cross paths with regional Pokémon League Champions. He wanted to battle each one, of course, and though he lost most of those attempts, his diligent training has now taken him to the top eight of the Pokémon World Coronation Series, where he once again found himself face to face with old friends and Pokémon Champions alike.
Ash learned something from each of the Pokémon Champions that he met or faced in battle. It would be hard not to; Ash always learned new techniques from his adversaries and friends, and though these regional Champions were often his toughest opponents, he learned from their strengths, their strategies, and their wisdom. The question that remains to be answered, then, is which Pokémon League Champions Ash has met during his travels, and who had the biggest impact on Ash's journey as a trainer, helping him to become one of the best eight trainers in the entire Pokémon world.
Lance From The Indigo & Johto Pokémon Leagues
Lance is the Pokémon Champion for the Indigo League in Kanto and the Johto League. He specializes in Dragon-type Pokémon, though his most famous Pokémon is undeniably his shiny red-colored Gyarados, which he caught after a daring adventure with Ash and his friends in the original Pokémon series. Lance is currently one of the eight strongest trainers in the Pokémon world, having lost the final match against Pokémon Champion Leon in the last iteration of the World Coronation Series.
Ash and Lance had quite a few adventures together, most notably in the original Pokémon series but in the next iteration of a Pokémon trainer.
Steven Stone From The Hoenn Pokémon League
Steven Stone was the Pokémon League Champion in the Ruby and Sapphire Pokémon games. Though never technically mentioned in the Ruby and Sapphire anime to be the Hoenn region's Pokémon Champion, he likely was during the time of this iteration of the Pokémon anime, as his successor Wallace was only introduced in the next series of the anime, Diamond and Pearl. Later, in the Pokémon The Series: XY special Mega Evolution Special II, Steven was confirmed as the Champion of Hoenn once again. Like Ash, Steven is also one of the top eight trainers in the world, though Ash, as the Alola Pokémon League Champion, was able to beat Steven in the tournament. His most notable Pokémon is undoubtedly his shiny silver-and-gold Metagross, which debuted in Pokémon XY.
When Ash and Steven first met in Pokémon Ruby and Sapphire, Ash was eager to get Pokémon training advice from him. Unfortunately, their meeting was interrupted by Team Rocket and a horde of angry Aron, but Steven did impress Ash with his Aggron's strength and explained the importance of evolutionary rocks for certain Pokémon. Steven's fascination with evolutionary rocks was continued when he reappeared in Pokémon XY, where he was working to learn about Mega Evolution. In the end, Ash and Steven's first meeting didn't result in a hard-won lesson, though Steven did impress the importance of leaving wild Pokémon's natural habitats in peace to Ash and his friends, and Ash has done his best to respect that lesson ever since.
Cynthia From The Sinnoh Pokémon League
Cynthia is the Pokémon Champion for the Sinnoh region, and just like Ash and Steven Stone, she's one of the top eight trainers in the world. Her trademark Pokémon partner is her Garchomp, a Dragon-type. Cynthia has appeared in the Pokémon anime more than most of the other Champions and has interacted with Ash and his friends a great deal throughout various iterations of the Pokémon anime. She was instrumental in helping Ash during several crises, especially regarding Team Rocket and their Sinnoh counterpart Team Galactic.
Though Ash has never officially battled Cynthia himself, he learned a lot from watching her battle his Diamond and Pearl rival Paul, as well as her various matches against of Sinnoh's Elite Four. The biggest lesson Ash learned from Cynthia, however, was that a Pokémon's brute strength isn't the only deciding factor in a battle, a lesson which Paul was forced to learn from Cynthia as well. She also taught Pokémon trainer Ash the value of respecting an opponent's strategies, even if he disagreed with their temperament as a Pokémon trainer.
Alder From The Unova Pokémon League
Alder was the Unova Pokémon League Champion during Pokémon Black and White. Alder is one of the few Pokémon Champions that Ash has properly battled during his journey, though the match eventually ended in Alder conceding defeat, as he had a difficult time getting his Bouffalant to cooperate. Alder is frequently seen as one of the least impressive Champions in the Pokémon franchise, and he was eventually succeeded by Ash's friend Iris, who traveled with him through Unova.
One impactful moment that Alder had in the Pokémon anime, however, was when he managed to stop a rampaging Gigalith from destroying a town by taking a moment to stop and understand what the underlying issue may be, rather than just battling it into submission. Alder finally found a nail impaled in the bottom of Gigalith's foot, and the once agitated Pokémon was incredibly grateful. In the end, Alder taught Ash that raw strength in battling wasn't as important as the friendship between a trainer and its Pokémon, an ideal that Ash has exemplified throughout his career as a trainer.
Diantha From The Kalos Pokémon League
Diantha is the Pokémon Champion in the Kalos League in Pokémon XY. Like Ash, she is one of the top eight trainers in the World Coronation Series. Her most notable Pokémon partner is her Gardevoir, who also has the capability for Mega Evolution. Ash had the privilege of battling with Diantha during his journey across Kalos twice. Though he lost both times, he did manage to knock Gardevoir down the second time, a feat that portrayed the close bond Ash had with his Greninja.
Diantha was instrumental in teaching Ash more about Mega Evolution, and the importance of his bond with his Pokémon Greninja. In the XY anime, Ash's Greninja ends up being able to Mega Evolve, in a way, without the help of a Key Stone. Diantha's powerful Pokémon battle with Ash allowed Ash and Greninja to begin to perfect this impressive and powerful trick, though it would take several attempts before they were able to fully utilize this ability. His experiences with Diantha laid the groundwork, however, for one of Ash's most important relationships with his Pokémon, perhaps second only to Pikachu.
Leon From The Galar Pokémon League
Leon is the latest Pokémon League Champion, serving the Galar region. He is also the current reigning Monarch of the World Coronation Series after beating Lance in their finale match last season. As such, the Pokémon anime posits that Leon is the strongest trainer in the world - it's no wonder that Ash has been so determined to battle him. Leon's trademark Pokémon is his Charizard, and Ash and Leon have had several adventures together, including battling the mythical Pokémon Eternatus to save the Galar region.
In Pokémon Journeys and Master Journeys, Leon has taught Ash much about Dynamaxing and Gigantamaxing, the battling gimmick only found in the Galar region. Leon is incredibly knowledgeable about the subject of Dynamaxing, as well as Mega Evolution, as he recognizes the bond that Ash shares with his Lucario. He also showed Ash the importance of letting yourself feel vulnerable - after Eternatus was defeated, Leon confided in Ash that he had felt helpless to stop it, and wondered what the limits of his strength as a Pokémon trainer might be. As a result, Ash learned that even the strongest trainer in the world can feel downtrodden and that it is important to acknowledge those doubts while finding a way to deal with them as well.
Which Pokémon Champions Have Been Succeeded?
Wallace, who specializes in Water-type Pokémon, was the Pokémon Champion in the Hoenn region in the Pokémon anime during Pokémon Diamond and Pearl. Wallace's main focus in the Pokémon anime, however, was Pokémon Contests, which involve a different form of battling. He encouraged Ash to enter the Wallace Cup, a prestigious Pokémon Contest, which allowed Ash to try out and perfect some knew and unorthodox strategies for his Pokémon battles. Later, in Pokémon Ultimate Journeys, Wallace and Ash had a Pokémon battle, and Ash was able to defeat him.
The more interesting Pokémon Champion replacement, however, is undoubtedly Ash's friend and travelling companion Iris, who traveled with him throughout the Unova region in Pokémon Black and White. At some point, Iris defeated Alder and became the Pokémon Champion, and is now, like Ash, one of the Top 8 trainers in the World Coronation Series, though he was able to defeat her in a match. While traveling together in Pokémon, Iris taught Ash a lot about raising Dragon-type Pokémon, perhaps unsurprisingly, as her dream was to become a Dragon Master. Ash's experiences with Iris allowed him to understand Dragon types on a deeper level, which later helped him raise several Dragon-type Pokémon, including a Noivern, a Goodra, a Dragonite, and a Dracovish.
Which Pokémon Champion Had The Biggest Impact On Ash?
Though there are several worthy candidates, it's hard to deny that Cynthia had the biggest impact on Ash as a trainer. Though others, especially Iris and Leon, have played huge parts in Ash's continuing Pokémon journey, it was Cynthia who taught him the true value of learning from his opponents, even if their approaches to Pokémon training were fundamentally different. Paul was Ash's most important Pokémon rival - they started off hating one another, but gradually grew to respect one another as well. That was mostly down to Cynthia's involvement; she encouraged both trainers to see beyond a Pokémon's brute strength and discover their needs as well as their other skills and battle advantages. Ash would come back to Cynthia's lessons often throughout the fourth iteration of the Pokémon anime, citing her as one of his inspirations for battling and becoming a Pokémon Master.