>>55862673Kanto: Never had a shot against Ritchie. Top 16 deserved.
Johto: Could have beaten Harrison, but all his best Pokémon would be too exhausted for his next battle. Top 4 at best.
Hoenn: Seemed to be on equal footing with Tyson, plus he was intentionally nerfing himself because he specifically wanted to use his Hoenn team. Could have won the whole thing, but I don't think he could have beaten Steven/Wallace for the Champion title yet.
Sinnoh: Tobias was designed to be unbeatable. Even if Infernape wasn't exhausted from Paul, and even if Ash had a perfect team of six, I still don't think he could beat Tobias. Top 4 deserved.
Unova: You couldn't pay me to PRETEND to care about Best Wishes so I'll just assume his Top 8 was deserved.
Kalos: Basically the same situation as Hoenn, could've beaten Alain with reserves or even just a bit better luck with his Kalos team. Might have been able to beat Diantha too, but since Alain presumably didn't then maybe Ash couldn't either.