Ash's best Pokemon rivals
Image Source: The Pokemon Company

Ash’s Top 10 Best Rivals in the Pokemon Anime, Ranked

Who remembers Ash's heated rivalries with these ten trainers?

Ash has has many brilliant rivals throughout his time in the Pokemon anime. These rivals have helped him overcome obstacles, given him the drive to complete the Gym Challenges, and naturally, been both huge friends and frustrations over the last 25 years. With Ash set to leave the Pokemon anime in the near future, we’ve gone ahead and compiled a list of his most formidable rivals. Without further ado, here are our rankings of Ash’s 10 best rivals in the Pokemon anime.

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10. Barry

Barry from Pokemon
Image Source: The Pokemon Company

While Barry was a frustrating rival for many in the Diamond, Pearl, and Platinum games and their remakes due to his hyperactive personality and constant rushing around, he saved himself by providing some tough battles and a decent team to go up against. In the Pokemon anime though, Barry seems to have had his personality carried through sans his skills as a trainer.

Barry played a rival to Ash throughout the Diamond and Pearl anime but failed to pose a threat, losing to Ash almost every time they engaged in battle. On top of this, Barry gets completely wiped out by Ash’s main Sinnoh rival, Paul. This was disappointing, considering he has one of the most challenging final battles in the Pokemon games. He ultimately failed to live up to the expectations of fans, thus earning him the bottom spot on this list.

9. Ritchie

Ritchie in the Pokemon anime
Image Source: The Pokemon Company

Ritchie is one of Ash’s first friendly rivals throughout the entire Pokemon anime series, with their history going back to the Kanto and Johto Leagues.

Ritchie was an exciting rival for Ash to go up against and maintain friendships with, mainly due to their similar Pokemon teams. Just like Ash, Ritchie’s partner Pokemon is a Pikachu, nicknamed Sparky. He’s also one of the only trainers in the anime series to give nicknames to all of his Pokemon, so he stands out from others as more of a representation of those who played the original games.

Ritchie was likewise a dedicated and strong trainer who paralleled a lot of Ash’s training styles, techniques, and personality traits, and was successful enough to make it into the top 8 in the Kanto League Championship.

If he’d only showed up more often, he would have been higher on this list. I’m not sure about you, but I, for one, would have loved for Ritchie to return later on in the anime with a more significant, recurring role so that he had an excuse to reappear in later generations of the show.

8. Kiawe

Ash and Kiawe in the Pokemon anime
Image Source: The Pokemon Company

Kiawe is one of Ash’s companions throughout his adventures in the Alola Region and plays the role of a powerful, friendly rival. Throughout the Alola Region episodes, the two are highly competitive and have a constant drive to battle and outdo the other with their skills. This resulted in them working each other up and becoming stronger not just as trainers, but in generally competitive or high-pressure scenarios.

Who else remembers their dramatic walk-turned-running race whilst searching for Tapu Fini, simply because neither of them wanted to slow down their pace in comparison to the other? Watching Ash and Kiawe sprint towards the rock, with their Pokemon desperately trailing behind trying to keep up was a hilarious moment, proving just how competitive and focused they were with one another. I mean, somehow they managed to turn a search for a Legendary into a competition – that takes some sort of rivalry.

Not only were Ash and Kiawe brilliant sparring partners and passionate competitors, but they also formed a strong bond of friendship during their adventures. Kiawe was a formidable trainer with a strong team and made the perfect friendly competition to keep Ash on his toes. Kiawe even made it all the way to the Alola League semi-finals, missing out on a battle against Ash in the final due to an unfortunate loss to Gladion.

7. Trip

Trip and Ash in the Pokemon anime
Image Source: The Pokemon Company

Trip is the character who played the rival role to Ash throughout his journey in the Unova Region, serving as a cocky, overconfident trainer known for being the winner of the Pokemon World Tournament Junior Cup. While he may have had some real talents as a trainer, his personality was less than desirable, making him a problematic character for fans to like. Seriously, this guy is like the Walmart knock-off of Paul. Sorry sweetie, we already have Paul at home.

Trip mirrors Paul’s toxic personality traits and overall annoying and frustrating characteristics, but lacks the depth of personality that makes Paul such a great rival. However, Trip managed to defeat Ash in battle every time they engaged in a match prior to the Unova League Championship. For this reason, he was a worthy rival, because he is so hateable, it makes you want to desperately cheer Ash on and watch him grow stronger so he can finally take the unbearable Trip down a peg or two.

Trip’s ultimate goal was to become the next Unova Pokemon Champion, and knowing that he’s so confident in his ability to do so makes him absolutely infuriating. However, Ash managed to shut down Trip’s plans completely by wiping him out in the very first round of the Unova League, finally getting one over his rival. Watching Pikachu take down Serperior is an extremely satisfying battle, and ultimately worked as a wake up call and reality check to Trip. Because of his defeat, Trip, who previously thought very little of both Ash and the Kanto Region, has his eyes opened and gains some level of respect for Ash.

6. Sawyer

Sawyer in the Pokemon anime
Image Source: The Pokemon Company

Sawyer is a young Pokemon trainer that creates an established friendly rivalry with Ash during the latter’s adventures in the Kalos Region in the Pokemon: XY anime. Because of Sawyer’s meticulous note-taking, he is able to study the techniques of other trainers and use the information he discovers to grow strong himself.

When Sawyer makes his debut, he’s pretty weak as far as trainers go. However, he uses Ash as an inspiration and begins taking notes and lessons from the other trainers around him. Across the duration of Ash’s time spent in Kalos though, he becomes quite the strategist and develops his skills to the point where he can defeat Ash in battle. Sawyer’s personal growth and hard-working personality make him a very likable character, and he was a brilliant addition to the list of friendly rivals for Ash to overcome.

5. Gladion

Glaidon from Pokemon
Image Source: The Pokemon Company

Gladion is one of Ash’s rivals throughout the Alola Region, most recognizable for using Silvally as his partner Pokemon. He’s a strong trainer who is very capable in battle, having defeated Ash numerous times throughout his Alola travels. However, Gladion isn’t just a solid opposition to Ash. He also has some significant character growth that led to him being well-loved by fans and known as one of the better rivals Ash has had.

Much of Gladion’s story and personality are carried over from the Sun/Moon and Ultra Sun/Ultra Moon games, meaning his relationships with Lillie and Lusamine still have the same complexity. Gladion debuts as a somewhat mysterious rival figure for Ash, but as the series goes on, he learns to open up to the other characters as well as strengthen the bond with his own Pokemon. It’s very satisfying watching little hints of Gladion’s personal growth, even from the way he used to look at Ash and friends with a scowl in the early episodes, to looking up to them with a smile and respect by the end of it all.

Gladion also really cements his bond with Silvally to the same sort of level as Ash and Pikachu, and learns to use Silvally’s memory disk / type-changing capabilities to his full advantage, making him a much stronger trainer in the process. Just watching Gladion pull off some of his moves, such as throwing a Fire Memory to Silvally at the last second to endure a Fire-Type attack and win his battle against Kiawe shows how much improvement he’s made as a trainer, finally working in sync with full trust between himself and Silvally as partners.

Ash and Gladion’s final battle in the Alola League is also highly considered to be one of Ash’s best rival battles. This is partially because of how close the battle is, with the two of them going round-for-round in victories until they both have just one last Pokemon to use in the final round of the battle. The battle also has a number of nail-bititng moments, such as when Ash’s Pikachu knocks itself out of the battle using Breakneck Blitz to ensure the knockout of Gladion’s Zorua. For all of Ash and Gladion’s clashes and time spent preventing Ultra Beast disasters, there’s no doubt he deserves his place on this list.

4. Gary

Ash and Gary in the Pokemon anime
Image Source: The Pokemon Company

Naturally, the iconic Gary Oak more than deserves his place near the top of the list. After all, he was Ash’s first rival in the Pokemon anime, all the way back to when Ash entered his first Gym Challenge and Pokemon League in the Kanto Region.

Gary was an intelligent and talented trainer with a history of being Ash’s childhood friend when they were kids. However, things changed once they were ready to set off on their adventures, and an intense rivalry is established right from the get-go. How could we possibly forget Gary’s “Smell ya later!” line that he’d use to brag about being one step ahead of Ash at all times? What an annoyance!

Gary’s mockery of Ash and boasting of his achievements aside, some of the best Pokemon battles in the anime have been between none other than Ash and Gary Oak. Gary’s Blastoise was an absolute force to be reckoned with in the anime’s earliest seasons, making the most of its type advantage over Ash’s Charizard and making Charizard’s eventual victory that much more gratifying. Plus, Ash and Gary’s dynamic has some significant development. When the dust settles after their battle, the two come to an understanding of one another and re-establishing their friendship with newfound respect.

3. Jessie & James

Team Rocket in the Pokemon anime
Image Source: The Pokemon Company

Very few of Ash’s rivals in the Pokemon anime can say that they’ve appeared in each Region alongside him to cause trouble and butt heads with him and his fellow companions. That’s exactly what Jesse and James have done though, and fans couldn’t have been happier to see it.

Sure, Team Rocket as an organization isn’t exactly a ‘rival trainer’ to Ash. At the same time though, it’s undeniable that Jesse and James as individuals are anything less than longtime rivals to Ash. Despite their plans to capture Pikachu and make Giovanni proud, they’ve also had several unique moments of bonding and understanding with Ash, and have grown right alongside him.

Because of this, Jesse and James have increasingly become more like an annoying rivals meant to stir up trouble and test Ash’s skills instead of a big, looming threat of any kind. They’ve been there right from the beginning to keep Ash on his toes and watch him grow as a trainer.

Who could forget the moments they’ve shared with Ash and the numerous battles that have gone down across each Region? It’ll surely be interesting to see if Jesse and James will be written out of the anime alongside Ash. If this is the case, we can only hope we will see Team Rocket blasting off again, Just one last time.

2. Alain

Alain in the Pokemon anime
Image Source: The Pokemon Company

Alain is a trainer from the Kalos region that possesses power and an incredible bond with his Charizard. He was able to utilize the likes of Mega Evolution to boost the capabilities of Charizard even further, and has made his mark as one of the most capable trainers in the entire Pokemon franchise.

This all allowed him to establish a healthy rivalry with Ash, and inspiring the latter to become stronger during his time in Kalos. Ash was absolutely wiped by Alain and his team in every single scenario, with the latter never losing a single one of their matchups – even when Ash utilized the likes of his Greninja, who is potentially his most powerful Pokemon of all time. On top of this, Alain always succeeded in keeping his promises to Ash, joining the Kalos league so the two could battle once more.

Alain’s powers went further unmatched in the Kalos League, enabling him to win and become recognized with the title of Kalos League Champion. There’s no doubt that Alain is perhaps Ash’s most powerful rival of all time and a very likable one in addition. However, one other rival proved more memorable and impactful than he was.

1. Paul

Paul and Ash in the Pokemon anime
Image Source: The Pokemon Company

We’re referring, of course, to Paul, the rival from the Pokemon anime’s Diamond and Pearl run.

Paul is one of the most emotionally and physically tough trainers Ash has ever encountered in his journeys, and is most commonly remembered for his terrible attitude toward the growth and development of Pokemon. As he prioritized brute strength over friendship with his Pokemon, he was the polar opposite of Ash as a trainer.

Because of this, the two had major conflict between them that further ignited the flame of their rivalry, especially when Paul decided to abandon his Chimchar in front of Ash. This turned out to be one of the most significant moments in the Pokemon anime, as Ash took in Chimchar as his own Pokemon and worked hard to raise it into an Infernape.

Ash and Paul’s battle in the Sinnoh League is undeniably one of the most memorable Pokemon battles of all time as well, with Ash’s Infernape going back up against the trainer who had previously abandoned it. Ash was able to gain the final victory over Paul, which caused the latter to finally gain a respect for Ash and establish a much more civil bond between the two. Although they don’t always see eye to eye, the two end up having respect and understanding for each other’s training methods and learning a lot from one another throughout their rivalry.

That’s it for Ash’s 10 best rivals in the Pokemon anime. Which one of them is your favorite? Be sure to let us know in the comments below, and check out the rest of our content here at Twinfinite for more Pokemon lists, news, and gameplay guides. We have a wide variety of topics, such as the top 10 most powerful Pokemon, 10 most likeable characters in Pokemon Scarlet & Violet, and best Pokemon Champions, ranked.

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Grace Black
Grace is a writer and digital artist from New Zealand with a love for fiction and storytelling. Grace has been writing for Twinfinite for one year and in the games industry for two years. She's an enthusiast of everything spooky, an occasional anime enjoyer, and a die-hard Ghost-Type Pokemon fangirl. Her favorite video games include Overwatch 2, Life is Strange, The Last of Us, Baldur's Gate 3, and Pokemon - all of which she will never tire of.