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I never quite understood this logic. Sure, the Orange Islands and the Orange League were made up for the anime, but it wasn't filler in the traditional sense. Important events still happened, such as Brock leaving and Charizard starting to listen to Ash, and those events were still referenced/carried over into future series. It's not like you can skip all of the Orange Islands arc and go right into Johto without missing anything. Not counting the Orange League victory simply because it doesn't exist in the games always seemed like such a weird reason to discount that victory. It wasn't a traditional League, but he still defeated the Orange League Champion and entered the Hall of Fame, so I think that should count for something regardless the Orange Islands being an anime only area.
Oh, that's an easy logic to understand if you subscribed to the "Ash is a loser, Red is better than him" meme that anime detractors are fond of using. It's a faulty rational to begin with you really break it down. The Indigo League, despite being "based" on the Gen I games, is unlikely the game-changing event that reveals who's the best Pokémon trainer is of the entire world. It didn't even bother to showcase the face of the champion, let alone their battle. Then compare that with Drake, who is not only the defending Champion of the Orange League but is so successful that he actually got bored of winning to the point he wishes to face a tougher opponent than the amateurs that came before him.
The irony is that the Orange League, despite being an anime-exclusive League, is the only League that has ever come closed to emulating how the Leagues functioned in the games. Four trainers to defeat before you face the defending Champion. The final battle is a full six-on-six match. Win, and your team get a picture taken and be placed in the Hall of Fame. Then you're free to go.
League Conferences in the anime are essentially glorified tournaments that you'll see in meta-gaming competition, and it would be disrespectful to imply that only the winner matters and everyone else are losers not worth looking into.
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