In 2019,Pokémon’s Ash Ketchum won a Pokémon League tournament for the first time in the Alola region, after coming close several times. However, he could’ve won the illustrious title of League Champion a decade earlier, if it weren’t for one wildly unfair match that irritates fans to this day.
Many fans argue that Ash’s Alola league victory wasn’t the most narratively satisfying time for him to have won a tournament. Ash’s focus had been much more casual throughout theSun & Moonseries, and many felt his team wasn’t quite up to snuff at the time, despite including some truly powerful Pokémon. For mostPokémonfans, winning a tournament shouldn’t simply be about having the strongest Pokémon, but about winning with thePokémon one has the closest bonds with, such as that between Ash and Pikachu. In fact, the one opponent to use powerful Legendary Pokémon is one of the most hated characters in the series: Tobias.

Tobias Represents Everything Wrong With Pokémon
Tobias’s Victory Destroys the Series' Themes
InPokémon Diamond and Pearl, Ash progressed quite a lot as a character and as a trainer. Not only was he still benefiting from the experience he’d built up across the previous three tournaments, but he had some exceptional story arcs throughout the era, such as his intense rivalry with Paul and his relationship with Chimchar. Ash had matured enough as a trainer to fully take on the duty of mentoring Dawn, and ultimately proved his kinder way of raising Pokémon superior to Paul’s cruel training. The Sinnoh League was the culmination of everything that came before, and was the perfect chance for Ash to take it all.
However, in that tournament, fans were introduced to a mysterious, powerful trainer by the name of Tobias. Tobias was given very little characterization, rarely speaking and mostly just looking tough. Tobias had the requisite six Pokémon necessary to compete, and was rumored to be a contender for the champion title.However,Tobias’s first battle soon revealed his secret: he had on his side the Mythical Pokémon Darkrai, with which he was easily able to defeat all his opponents. No one even saw his other Pokémon until Ash, and it took Ash four of his six Pokémon just to defeat Darkrai.

It’s obvious, from a meta perspective, that Tobias was created specifically to keep Ash from winning the tournament here. He serves no other role in the story, has no characterization, no bonds with his Pokémon that we see, and wins the rest of the tournament offscreen. Tobias’s victory undermined the themes of the season that dealt with raising Pokémon with respect to bring out their true power, and his late introduction meant that there was no emotion connected to his victory, the way that, say, the victory of a long-time rival of Ash might’ve had.
Ash’s Team Was At Its Best, And Should’ve Been Rewarded With Victory
While in all future tournaments, Ash would rely exclusively on Pokémon he had caught in that region, the Lily of the Valley Conference for the Sinnoh League saw Ash bringing out some of his old standby Pokémon for one last big battle. Pokémon like Sceptile and Heracross appeared for the first time in hundreds of episodes, giving Ash the greatest possible team compositions he’s ever had. At last, Ash was doing as fans wanted and putting together the ultimate team. It really felt like he could go all the way this time, at least until Tobias showed up.
Ash was even able to change his team up between battles, using his Sinnoh team against Paul before pulling out the classics for the next round.Had Ash been up against any other trainer(short of Cynthia),he’d have stood a fantastic chance at winning in the semifinals, and potentially the finals as well. Ash’s Sceptile, after all, was powerful enough to take out Tobias’s Darkrai, something no one else in the tournament (including Tobias’s opponent in the final round, apparently) was able to do. Ash could have, and should have, won the Sinnoh League.

What’s worse is that, under most competitive Pokémon tournament rulesets, using Mythical Pokémon like Darkrai is generally banned. Since these Pokémon are so difficult to obtain in the games most of the time, only distributed rarely, it’s generally considered fairer to remove them from play entirely, although there have been occasions where they were allowed. One could only imagine that similar rules would be in effect in-universe for the anime as well. The only other trainer to use a Mythical or Legendary Pokémon in an anime tournament is actuallyAsh himself, with Melmetal.
Ash Deserved to Win for Thematic Reasons, Too
The Diamond and Pearl Season Felt Like It Was Leading to Ash’s Success
Many fans resent Tobias to this day, due to how wildly unfair his match with Ash was. Looking at how theDiamond and Pearlera played out, it was the perfect opportunity for Ash to take home the trophy.More so than almost any other series, Ash was at the top of his game, and the story was reinforcing what a good trainer he had become with his relationship to Chimchar and conflict with Paul. Defeating Paul in the League tournament was one of the anime’s greatest moments, so it’s a shame that it’s followed immediately by one of the worst battles in the entire series.
Tobias never should’ve even existed as a character, andAsh’s battle with Paulshould’ve been his final round, delivering him both the well-deserved trophy and a moral victory. It would’ve been the perfect way to cement Ash’s legacy, and would’ve set the stage for an anime reboot with the fifth generation, which was already something of a reboot on the games side of the franchise. Instead, because thePokémonanime was afraid to move on without Ash, or to even let Ash succeed, fans were given one of his most disrespectful losses of all time, and that put a damper on what is otherwise one of the anime’s greatest eras.
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Pokémon follows Ash Ketchum on his journey to become a Pokémon Master, accompanied by his loyal Pikachu. Released in 1997, the series explores Ash’s travels through various regions, where he encounters new friends and challenges, underscoring the themes of adventure and teamwork.