Unlike the Pokégirl thread, where most posters actually took into consideration the criteria that OP gave, this thread hasn't followed that. However, because it's easier for me to do it that way, I am going to break it down by the criteria
@Ignition gave.
-Their teams
7. Max
6. Sophocles
5. Kiawe
4. Cilan
3. Tracey
2. Brock
1. Clemont
-Their personality
7. Max
6. Sophocles
5. Tracey
4. Brock
3. Clemont
2. Kiawe
1. Cilan
I realized after making this personality list that it's very distinctively broken down by era, besides Sophocles who just annoys me. The bottom 4 are all Gen I-IV, and the top 3 are all Gens V-VII. I think to me it's just that over time in the Pokémon anime, the writers realized how to elevate the male companions to the level of importance and focus that the female companions get, which is something I really didn't see with Brock and Tracey, who were very clearly third wheels, and Max who was a fourth wheel. Cilan's personality often outshone Iris's, Kiawe's seems more emphasized than
any of the girls', and Clemont's added a funny dynamic to the XY group that at least made him feel not as much of a third wheel as characters from Gens I-IV.
-Their goals
7. Max
6. Sophocles
5. Tracey
4. Brock
3. Cilan
2. Clemont
1. Kiawe
Just going to talk about the top 3
Cilan - first male companion to have his own rival
He also had his own goal, and I truly thought they were going to elevate him to S class connoisseur by the end of it, when they mentioned he was only A. Surprised they did nothing with that after mentioning that rating scale. He also should have continued to Kalos with Ash - not only because it's France and perfect for the food, but connoisseurs were actually mentioned in Kalos, one of them as a judge at one of the showcases, and that could have been his job in Kalos tbh, and the reason he stays in Kalos at the end when Ash continues to Alola. However, despite the negatives I just mentioned, just the fact that he's the only male companion to ever have his own rival and actively battle her multiple times, this makes him automatically better than anything before. The only reason I mentioned those negatives above is because I still felt they could have done more with him, which could have potentially elevated him to #1 or 2.
Clemont - even though they messed him up between his gym battle and the Xerosic arc, the buildup to the gym battle, his desire to be like Ash, and the Xerosic fight, both during and after the arc, giving him more to do in a villain arc than previous male companions, are what elevate him to me to that #2 spot.
Kiawe - only companion ever to join Ash in competing in the league, which to me is the best goal in the whole show
-Interactions with Ash + the other Main Characters
8. DP Brock
7. Tracey
6. Sophocles
5. Kiawe
4. Brock
3. Max
2. Clemont
1. Cilan
Overall ranking based on combining the above 4:
When I assigned a point system to the above and used it to calculate the overall ranking, Max and Sophocles ended up tied, so my final tiebreaker is just that I like Max more. Sophocles feels irrelevant to me and I wouldn't miss him at all if he didn't exist, I still feel the SM saga overall could move along just fine, with minimal differences/changes. Max was a cool guy to be the first younger sibling, it was interesting to have a group of 4 because of him in the episodes where they split up into 2 and 2 for example, and I liked his dynamic with May which is why I put him #3 on character interactions.
7. Sophocles
6. Max
5. Tracey
4. Brock
3. Kiawe
2. Cilan
1. Clemont
I really wish Chespin evolved
Because of Quilladin and Chesnaught debuting so late, as more and more episodes happened, 90+, and they still hadn't debuted yet, I was actually convinced it was because they were saving their debut for Chespin's evolutions, so I was even more disappointed than I would have been otherwise, that it never evolved. For example, when Delphox debuted so early, the second-earliest of any starter final stage (Blaziken debuted before AG even started), I immediately set my expectations low for Serena to ever get it, and that ended up being the right move. I did not do the same with Clemont and Chespin
He felt like Ash's best bro during the middle of XY.
By this I'm assuming you mean that he did not feel the same after the gym battle. I agree with you and I wish they had made Clemont 8th. We always talk about how anime does not equal games, and this was a perfect opportunity for them to take advantage of that and make Clemont the 8th gym, especially considering that the league was at Lumiose City so it would have made sense anyway for the final gym to be right there in the same city as the league. I also wish it had been a 6on6 2-episode battle, in which he used Dedenne, Bunnelby, Chespin, Luxray, Heliolisk, and Magneton.
hmm for me it would probably be Brock >Kiawe > Clemont > Cilan > Sophocles > Tracey > Max
You know I feel like the main problem with Tracey which has resulted in some people not liking him or forgetting about him is do to the fact that he really didn't get that many episodes as a traveling companion by this I mean when you really look at how many episodes Tracey appeared in as a traveling companion compared to the other male traveling companions you will notice it breaks down like this:
Brock was a traveling companion for all of Kanto, Johto, Hoenn(which for simply sake includes the Kanto Battle Frontier), and Sinnoh. While Max go all of Hoenn(which for simply sake includes the Kanto Battle Frontier), and Cilan got all of Unova+ the Decolore Islands and Clemont got all of Kalos, while Kiawe and Sophocles are getting almost all of Alola to appear, so all of them got plenty of episodes to appear in and had a good amount of time to developed regardless if they did get a lot of development or not however if you look at Tracey he got the Orange Islands however the problem with this is since the Orange Islands wasn't that big of a series or an arc being only about 35 episodes long with Tracey only appearing in about 33 episodes, which is nothing compared to the amount of time the other Male Companions got.
I feel like Tracey would have really benefited going to Johto with Ash, Misty, and Brock(if it was going to be a situation where Brock was going to return regardless) as that would have meant Tracey would have had a bit more time to developed or show off a bit more heck and if they really didn't want to have Ash have 3 traveling companions with him going to Johto they could have just had it been Ash, Misty, and Tracey traveling through Johto and then at the end of Johto when Ash is going to Hoenn they could have Tracey then choose to become Professor Oak's assistant and then still have Brock reunite with Ash and travel through Hoenn with him.
I agree with what you say about what Tracey would have benefited from, but I get the sense that at the time the writers added and then removed Tracey, they weren't even thinking about how to give him development to compare to future companions, and in fact it was very possible they hadn't even thought of the concept of future companions and just thought it was going to be Ash, Misty, and Brock forever, with Tracey being a temporary replacement who had served his purpose. I even think if they looked back at his situation now, considering how many traveling companions there have been since then, they would probably agree with you, it's just that at the time, the concept of rotating traveling companions each region, and giving each of them proper development, wasn't even in the writers' mind.