At the young age of 10, Ash set out to be the greatest Pokemon Trainer ever. He has not waned from this goal, which is quite admirable. Over time, he has suffered many defeats and enjoyed a few well-earned victories. These experiences have given Ash the knowledge necessary to achieve his dreams, even if it did take a long time.
Some defeats stand out because they were avoidable had Ash planned better or understood his Pokemon better. Conversely, some victories feel extra special because Ash takes the time to understand the challenge he is facing and how to use his Pokemon to his advantage. All things considered, Ash has proven himself to be a prodigious Trainer in the Pokemon anime series, even if he is prone to clumsy mistakes.
Defeat - Charizard Falls Asleep
Charizard and Ash have a long, emotional history. Ash catches the Pokemon when it is just a Charmander. It is abandoned by its previous owner, but it finds a second chance with Ash. As the Pokemon evolves and its strength increases, its respect for its Trainer decreases. Charmeleon tends to simply ignore Ash's commands, and things only get worse when it evolves into the mighty Charizard. Instead of taking Ash's orders, the fire-breathing monster would rather take naps. Despite this, Ash doesn't give up on Charizard because it knows a very powerful move - Seismic Toss.
During the Indigo League tournament, Ash finds himself up against Ritchie. The Trainers are two sides of the same coin, as they both have a Pikachu. Although Ash knows that Charizard can be recalcitrant, he decides to trust his friend. This turns out to be a bad move, as Charizard falls asleep during the match, resulting in Ash losing. The loss is crushing, and it is among the first big defeats that he faces. The loss is also notable because it seems to veer away from the logic established by the video game series. Typically, within the Pokemon video games, high-level Pokemon will not listen to Trainers with insufficient badges. Despite Ash having enough badges to enter the Indigo league, Charizard still refuses to respect Ash. One could argue that it is somewhat deserved, as a good deal of the badges Ash received in the Indigo League season were more like charity gifts rather than badges won through skill.
Victory - Pikachu Defeats Lt. Surge's Raichu
When Trainers catch Pokemon, they usually aim to evolve their creatures so that they can become as powerful as possible. Ash's Pikachu proves to be an exception to this because it never wants to evolve. This is despite the fact that becoming a Raichu would give it access to new moves and make it more powerful. At times, Ash has asked Pikachu to evolve, but he has respected the yellow rodent's wishes and he has never forced it to do so. Pikachu is truly tested when it goes up against Lt. Surge, the Electric-Type Gym Leader of Kanto. He has a very powerful Raichu, and he mocks Ash for not evolving his Pikachu. Instead of succumbing to the pressure and evolving his friend, Ash instead trains Pikachu and relies on strategies to outsmart his opponent.
When he has a rematch against Lt. Surge, Raichu lets out a powerful Thunderbolt attack. Fortunately, Pikachu is not affected by it because it sticks its tail into the ground. This grounds the rodent, making it immune to the Electric-Type attack. As Raichu is recovering from letting out such a powerful attack, Pikachu uses its speed advantage for a Quick Attack that takes Raichu down, bringing Ash the victory he desires. Through Ash's win, he proves that Pokemon isn't just about collecting the Pokemon with the strongest stats. It's about working with the Pokemon that one loves, and learning how to make winning strategies using them, regardless of their weaknesses. He also illustrated that evolving a Pokemon isn't always the best move and that pre-evolved forms also deserve attention.
Defeat - Pikachu Loses to Meowth
Meowth and Pikachu are two Pokemon that have always been inextricably linked. In the Pokedex, Pikachu is number 25 and Meowth is number 52. Furthermore, one is a mouse and the other is a cat, setting up a natural relationship of animosity between them. This relationship is illustrated in the anime series, as Team Rocket has a Meowth that wants nothing more than to capture Pikachu and present it to Giovanni, the boss of their criminal organization.
In the Ruby and Sapphire season of the series, Ash finds himself steadily working his way up the Hoenn League until he faces off against Tyson. The battle is fierce, and it eventually comes down to Pikachu squaring off against Tyson's Meowth. Thunderbolts and Iron Tails fly around, but none are enough to take the Meowth down. Eventually, after Meowth counters Pikachu's Iron Tail with its own Iron Tail, Pikachu is down for the count, making Tyson the winner. Any defeat for Ash is sad, but it is extra harsh when it comes from the cat that has been Pikachu's mortal enemy since the beginning of the series.
Victory - Ash Becomes World Champion
Pokemon Journeys has Ash and Goh traveling to various regions. Goh wants to catch every Pokemon. Ash still wants to be a Pokemon Master. He enters the Masters Eight Tournament in Galar, and he ends up making it to the finals where he goes up against Leon. It is a fierce battle that leaves Ash down to Pikachu and Leon down to Charizard. Pikachu takes a good beating, but it is somehow able to withstand it and defeat the fire-breather. It is an epic battle and a victory fitting for someone who has been chasing their dream for so long.
The Pokemon Company has announced that in 2023, the series will be saying goodbye to Ash and Pikachu. It will be a bittersweet farewell, but after following his journey for so long, his departure does feel like the natural direction for the series to go. It could have implications for the Pokemon games going forward, as both Ash and Pikachu have served as series mascots for decades.