>>41922867In the games? Nah, he's a very realistic guy.
In the anime? I'm rather upset about how the Lana fight went, but the Alola League in the anime was pretty much designed to let Ash win with how he hadn't gone on a real adventure and caught any actual Pokemon - he'd have to have brought back older mons to have enough of a team to compete, and we know the anime would never allow that in this day and age.