Ritchie wasn't that insulting because it wasn't his fault whatsoever;
Harrison was the only both decent and fair loss which Ash had;
Tyson wasn't that bad (aside the Meowth);
Tobias was the most enraging because the battle itself was unfair, but not that bad because he showed that Ash was a very competent trainer;
Cameron was the most preposterous. He was dumb and irresponsible, added to the fact that, if wasn't for Ash, he couldn't participate and had only five pokemon, one of them was a shillmon. His victory was yet another way gamefreak used to shove Lucario in our throats.
Allan was the most humiliating (and a bit preposterous). The plot ignored all the personal growth which Ash achieved throughout the region to the point of making Greninja lose due to exhaustion and Charizard, which received a lot of damage, ended up with JUST a trembling in the knee. Sum this to the expectations that people were holding and there you go.
