Pokémon’s Ash Ketchum took home his first trophy far earlier than his Alola League victory over Gladion, yet despite that fact, Ash had a reputation as a “loser” for a long time. It’s almost as if fans consider his first victory invalid, but why is that the case?
Ash’s first victory was actually in the Orange League, a tournament set up in theanime-exclusive location of the Orange Islands. After gathering the local badges, Ash was permitted to battle the Orange League’s “Supreme Gym Leader,” Drake, a battle which takes place across two episodes: “Hello, Pummelo!” and “Enter the Dragonite.”

The Orange Islands arc took place immediately after the Indigo League, meaning that Ash actually won the second title match he participated in. Many fans feel this doesn’t count, however, and the victory has an asterisk next to it in many fans' minds to this day.
The Orange League Was Far From An Ordinary League Tournament
The reasons why many fans discount Ash’s Orange League victory are twofold, with one in-universe objection and one out-of-universe objection. The in-universe objection centers on the Orange Islands' league structure and how different it is from the various other leagues seen throughout the series.
First, the Orange League only has 4 badges, as opposed to the usual 8 needed in most leagues.The Orange League also requires more than just a Pokémon battle, as competitors must take part in a team-based physical challenge alongside their Pokémon in addition to a battle with the leader.

The Orange League also didn’t have a tournament with many competing trainers at the end, either. Instead, Ash faced off with the aforementioned Supreme Gym Leader, and defeating him in battle was sufficient enough to receive the trophy and be declared a champion of the League.
The out-of-universe reason most fans dislike Ash’s win in the Orange League is that the Orange Islands were literally invented for the anime, as a means of buying time while theGoldandSilvergames were being completed.Thus, the Orange Islands are the closest thing to a true “filler” arc thatPokémonreally has.
Does Ash’s Orange League Victory Deserve to Be Forgotten?
Ash’s Orange League Victory is as Valid as Any Other
However, when one thinks about these complaints, they quickly fall apart.The Alola League was also very unconventional; the Alola region doesn’t have badges at all, and so basically anyone who wanted to participate was allowed.Even Team Rocket’s Jessie and Jamesmade it through the preliminary round of the Alola League.
The Alola League also had some very unusual structures in how the tournament went about. While it did have a typical tournament at the top, it opened with a “Battle Royale” consisting of 151 trainers, something no other League has been shown to have.
Even the out-of-universe reasoning is pretty weak; there have been plenty of locations, characters, and challenges invented for the anime.The tournament structure the anime uses for the Leagues in general isn’t based on anything from the games, either, after all.
As such, Ash Ketchum’s Orange League victory is every bit as valid as his champion standing from Alola, or his World Coronation Series match with Leon. Consider Ash’s win here a preview of his eventual success inPokémon’s later league tournaments.