At what point did Ash go from rash rookie to skilled trainer?

[WyndonCalling]

I suppose this speaks to the disconnect between Ash's battling feats and his slapstick personality, but... I think it has to be as early as Surge, right? Of course, there's zero implications for his character development or much of how others perceive him, but de facto having three badges is where notable rookies start to simply become contenders I'd have thought (though I confess with being far more familiar with how the games handle that trajectory).

At what point does Ash actually begin to inhabit the skin of someone who's swept through multiple Gym challenges and been a Champion contender for multiple regions? That's a much more interesting question, and probably one closer to the intended spirit of the OP lol

 

[Daren]

I suppose this speaks to the disconnect between Ash's battling feats and his slapstick personality, but... I think it has to be as early as Surge, right? Of course, there's zero implications for his character development or much of how others perceive him, but de facto having three badges is where notable rookies start to simply become contenders I'd have thought (though I confess with being far more familiar with how the games handle that trajectory).

The confusing part is I think he was intended to be a very good trainer in latter Kanto who got overly cocky at the league; it's notable he didn't lose in the league because Ritchie was better than him but because of Team Rocket sabotaging him before the match, and then in the Orange Islands he outright defeated a (show only) champion, back when gen 2 was going to be the final game set and by extension the end of the anime.

I've mentioned this in another thread but I think there are a few parts where you can really see the stretch lines from the show having been extended; one very obvious one people noted even at the time is how much slower Kanto became after Koga was defeated.
And he goes back to making beginner mistakes over and over as a result.

At what point does Ash actually begin to inhabit the skin of someone who's swept through multiple Gym challenges and been a Champion contender for multiple regions? That's a much more interesting question, and probably one closer to the intended spirit of the OP lol

I'd say AG is the obvious one because he just barely lost to the league winner despite handicapping himself then when no longer holding back was able to fight Legendaries on even footing and beat opponents supposedly (maybe a dub only line) just below the Elite Four and get invited to join said group.
But DP backed away from that and he got absolutely crushed by the league winner this time and was no longer able to fight Legendaries on even footing.

 

[Sai]

Even in Johto Ash seemed too good for being still a rookie at the time. Most of the Johto Gym leaders besides Claire weren't portrayed as too strong. Whitney just had trouble with rollout but the others weren't that powerful. Any other Ash would have annihilated Bugsy, Morty, Chuck, Jasmine far easier.

 

[Gengarzilla]

I think I'd narrow it to somewhere between his Gym battles with Clair. That first one was going pretty poorly before it got interrupted, and you'd probably expect the Ash of this era to ignore the hint and throw his regular squad through the wringer again. Right? Nope. He straight up calls the professor, by his own volition, and has Snorlax brought in to fight the Kingdra lead who previously shrugged off everything Ash tried last time.

This is Ash Ketchum taking the time to think things over instead of ramming his head against a wall. Knowing that he couldn't lay a mark on Clair's first Pokémon before, Ash pulled out a reserve which he knew beforehand was particularly powerful, at a time he actually needed its power, and without anyone telling him to. Brash rookies don't do this.

 

[jbmasta]

AG was where he really focused on teaching and honing new moves for his Pokémon, with one example being the focus of an episode (Treecko learning Bullet Seed). Brawly remains one of his only gym leader rematches where he didn’t use the same line up as the first match. This attention went up to eleven in Battle Frontier, where he’d call in reserves based on what he knew of his opponent and keeping the powerhouse moves until tactically ideal. Torkoal of all Pokémon held it’s own impressively well against Registeel.

DP cemented as Ash a strategist, both off the battlefield and on it. He was always good in a corner, but this series showed him developing moves well ahead of time, most notably Countershield which proved reliable from the time Ash came up with it right up to the Sinnoh League (and good enough for Paul to adapt!). DP also has one of the only gym battles that wasn’t one on one where Ash didn’t lose any Pokémon, everyone who fought Crasher Wake’s team avoiding the swirly eyes.

 

[FelipePR]

The confusing part is I think he was intended to be a very good trainer in latter Kanto who got overly cocky at the league; it's notable he didn't lose in the league because Ritchie was better than him but because of Team Rocket sabotaging him before the match.

-He didn't lose because Team Rocket sabotaged him before the battle, this only rendered his Pidgeotto useless, which would most likely not be able to defeat Sparky, as his Bulbassaur would hardly defeat Zippo.

-Ash lost because his Charizard didn't obey him, because he didn't have the respect and didn't act in tune with all of his Pokémon, unlike Ritchie. And in that sense, Ritchie was a better trainer than he was.

 

[Turbo]

I want to say Hoenn - Sinnoh as Hoenn is when he solidify his “Ash” style where Sinnoh is when it expanded so I think it depends how you like to view those two

Kanto: Beginner
Barely understood anything and got badges because of his character and personality in cases
Orange Islands/Johto: Understood Basics
Had better understood battling and other Pokémon stuff thanks to Misty Brock and Tracey
Hoenn/Battle Frontier: “Mastered Basics” and honing his more unorthodox/unpredictable style
He was a mentor to May and Max and by the end of the Battle Frontier you can see the style Ash is now known for in the Brandon battle
Sinnoh: Evolving Trainer
His style and attitude changed and grew thanks to Dawn and Paul, from training his Pokémon better, new tactics like spinning, perspective as a trainer etc
Unova: Leaning into the unconventional
Hard for me to point something for Unova since it was a soft reboot but I noticed that he started using stuff he hasn’t used traditionally whether it’s his first rock type in Roggenrola/Boldore or that Pokémon like Snivy knows attract, he was expanding his knowledge and battle possibilities even if skill wise he was questionable
Kalos: Experienced Trainer
A more polished Sinnoh and Hoenn Ash as he has more experience and leveled confidence
Alola: Balance and being more intuned with is his team
Learns to take care of Pokémon better since he’s more at “home”, has a better mental state here and learns Z moves
Journeys: ??
?? Only because it’s not finished, I can make claims that he’s learning about what his Pokémon want (ex: Gengar, Lucario, Sirfetch’d) but skill wise he’s better than XY as he’s being pushed to do more stuff and explore more options

So if I had to label his skill level
Kanto: novice
Johto: rising star
Hoenn-Unova: Gym leader (at peak, weak Elite 4)
Kalos-Alola: Low Elite 4
Journeys: Elite 4 - Low Champion

 

[-PokemonBattleFanatic-]

At the end of the day all versions are inferior to the purple haired Brandon look-alike.

Ash wasn't quite able to put it all together and do it consistently.

Paul checks off all of the boxes

• Battling
• Training
• Rotating
• Experience
• Capturing
• Intelligence
• Planning