Ash routinely ends up in the top of each region's league tournament. He is undisputably in the top 16 trainers OR BETTER in every single region. He has been offered a job as a Frontier Brain. He has manages to come up with strategies that regularly astound, confound and defeat professional Pokémon Gym Leaders. He has saved the entire planet from destruction absolutely no fewer than 18 times to date. He has played a crucial role in disbanding FOUR crime syndicates and has severely weakened a fifth's standing in a neighbouring region. He has encountered every type of Pokémon it is possible for him to have met, including every Legendary and Mythical Pokémon, with the exception of a pair of computerised ducks.
But because he hasn't won a second trophy, he's a failure. Yeah, alright.