Ash has faced-off against tons of talented trainers throughout his Pokemon journey. Though the young trainer from Pallet Town has gained a reputation among the Pokemon fan base as someone who constantly comes short in big moments, Ash has never shown a lack of effort in his quest to become a Pokemon Master. Ash, Pikachu, and their many companions have come face-to-face with some of the most talented trainers the Pokemon anime has to offer. There have been plenty of wins to celebrate, but the losses seem to leave a longer-lasting impression.