In the Pokémon anime, Ash has often been accused of being a character who doesn't grow or learn from his mistakes. His ultimate victory over his rival Gary in the original series, however, proves that Ash actually grew quite a lot over the course of his Pokémon adventure. Though Ash's journey is long, it is one that is filled with genuine growth.
In the early Pokémon anime, Ash behaves much like a child. He whines, complains, and gets into fights with Misty, just like one would expect from a ten-year-old boy. He doesn't accept his losses graciously, especially when it comes to his chief Pokémon rival Gary Oak. Gary, admittedly quite a jerk early on, always manages to rile Ash up, whether it's by choosing the Pokémon he wanted as a starter, or showing off his impressive Pokémon badge collection when Ash barely had any. No matter what Ash did, Gary always one-upped him, and that would drive Ash mad to no end. In fact, a lot of Ash's early motivation is just to beat Gary, even in areas that don't matter, like the size of a Pokémon. That applied to battles, too, up until Ash's match with Gary in the Johto League Silver Conference.
Ash Proves His Character Growth After Finally Beating Gary
Over 250 episodes into the series, Ash and Gary have a dramatic match-up in the Silver Conference, both having made it to the Sweet Sixteen tier, beating out hundreds of others. The battle itself puts both trainers' full skill on display, utilizing the rarely seen 6 versus 6 format. Ash battled with his Tauros, Muk, Heracross, Charizard, Bayleef, and Snorlax (a rare fight without Pikachu). It all came down to Gary's Blastoise versus Ash's Charizard, and despite having the disadvantage due to typing, Ash emerged victorious thanks to his unusual strategies. Ash celebrates his win, naturally, but that's when he manages to surprise. Instead of gloating to Gary and rubbing it in, Ash and Gary have a quiet conversation that night, and Gary admits that Ash won fairly, and that he'll be cheering Ash on from the sidelines in the next round, renewing a childhood friendship.
Related: The Secret Reason Ash Abandons His Pokémon is Brock & Misty
Ash from the first season of the anime would surely not have reacted that way. He very much enjoyed gloating at the time and likely would've made faces along with insults. But 250+ episodes had passed, and Ash really did grow over that time. He learned to fight fairly, no longer crushing inexperienced trainers with his high-level Charizard. He learned to get along with Misty, and he even began to understand Gary better, as Gary himself also grew up a bit. By the time of the Silver Conference, he's able to accept his loss, and Gary is in fact already considering a career in Pokémon research like his grandfather, Professor Oak. While Ash's growth might have been slow and uneven over all that time, this scene proves that he did mature. In fact, Ash's growth is the reason some find him "boring" in later seasons--he's no longer acting out like he did in the anime's beginning.
Given that the Silver Conference represented the end of the original Pokémon series with Misty and Brock, acknowledging Ash's growth with this win, even if he didn't take the whole conference, was a big deal. It began with Ash versus Gary seemingly hating each other in Pokémon, and it ended with Ash versus Gary, once again friends.