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Strongest: Kiawe, Brock to a certain extent
Weakest not including Max given he was still a kid: Tracey because he rarely battled and even as an artist, he was still rather one dimensional, and Cilian because while he was good at battling and had an okay personality, he had no real character development and mostly relied on being a “connoisseur” of random things gag most of the time and that gag got old rather quickly, and the most interesting thing about him was that he had a fear of Purrloin but it was never explained or brought up ever again. The episode ended on the cliffhanger of Cilian telling Ash and Iris how the phobia developed. Dawn’s fear of Plusle and Minun while being one episode only was explained along with why she hated being called DD by her childhood friends. Cilian’s fear was only used for one episode and then it was like it never existed.
Brock easily destroyed kiawe despite having type disadvantage, even though kiawe might have improved he so have brock's MS and his other pokemon. He is easily the strongest male companio.
That was back then brock was never utilized properly in OS and AG he id more in his cameo in SM, he destroyed kiawe's ace easily so unless kiawe in one episode beats bock properly he is inferior to brock.
Kiawe is not on the same level as Brock. Their battle made that clear. Kiawe did improve later on, but it would be silly to think Brock hasn't improved aswell since he is a gym leader which means he is constantly battling someone.
Even if Brock didn't improve, he wouldn't be defeated, because Brock's Mega Steelix still is far stronger than any of Kiawe's current pokémon. Not to mention he still doesn't own a full team yet.
If Clemont didn't get any boost after XYZ, then i reckon Kiawe would probably win.
If Clemont gets a Z-move, then i reckon he could beat Kiawe.
Either way, beating the other wouldn't be easy, since Clemont is intelligent so he can come up with some good strategies, while his Luxray is quite strong, his Helioptile is quite fast and his Bunnelby is quite resistant. However, Kiawe has the power advantage when it comes to his moves and also his Turtonator has type advantage against most of his pokémon, since Dragon is resistant to Electric.
Either kiawe or brock. Most people forget mega steelix was very weakened by kiawe and kiawe was barely strong then. He's very strong now. Whereas Brock was a loser when he was in the series. So probably kiawe
It's hard to define Brock since he's as inconsistent as Ash. He was during the era the male companion was just a third wheel who suffered the Worf Effect outside the odd limelight episode, while the others tended to get more careful checks to their prowess, especially Kiawe.
(going by the last time we've seen them, as hypotheticals can stretch things out a bit too much)
Kiawe (W/Z move)
Clemont/Brock/Kiawe (no Z move)
Cilan
Sophocles
That one guy that no longer resides on Oak's lab because IDK, he's probably dead by now
Ranking aces:
Turtonator (W/Z move)
Mega Steelix/Luxray/No Z move Turtonator (this one's a bit iffy, but oh well)
Steelix
Vikavolt (Vikavolt gave a good fight to Charizard, who almost KO'd Lycanroc)
Crustle
err.....was it Scyther?
Kaki and Takeshi are tied as the strongest male companions from my viewpoint. As for the weakest, I'd say that Kenji would get that title since his strongest Pokemon was Strike, yet it never did anything remotely impressive.