This episode has some really good moments. Although I don't think these scenes have much to do with this particular episode's plot, they are referenced to at the very end of Sinnoh. And maybe if Cynthia is the champion Ash ends up battling in the end, then these scenes will be some of the most important ones in this anime's history, maybe. That's the fun of analyzing, so I'll give it a try.
As usual, I'm going to stay away from the TG parts.
Ash and Cynthia both really stand out in this episode. Ash sees sort of his "dark" side, here, as he ignores Chimchar's injury in favor of trying to chase TG down, a disregard similar to Paul's after his battle with Cynthia. Worse than that, the reason Chimchar is so injured is b/c Ash ordered Pikachu to use Volt Tackle (although to be completely honest, in the scene itself it looked okay; I think this is the negative consequence of not showing a very serious looking injury to Croagunk after it's impaled by Poison Sting, so that Toxicroak's attack would look deadly), a move that Paul has criticized Ash a few times for using. This is the closest Paul comes to being right about Ash's flaws, but unfortunately for him/fortunately for Ash, Paul is not here. But Cynthia is here, and she treats Ash quite kindly about it. And Chimchar forgives Ash as well, once it sees Ash close to tears. This is the 3rd time, now, in a recent span of episodes, that one of our heroes has started to cry over his/her pokemon, so maybe this is a little overdone. But this scene feels a bit more powerful than Dawn's, in that Chimchar's decision to place it's paw(?) on Ash's cheek is a relevant decision. B/c as Cynthia says, Chimchar has been through a great deal of troubling events, with both Paul and Ash; Chimchar's sympathetic gesture serves as a sort of positive judgement for Ash. It's funny in a way, in that I think Chimchar would have done the same for Paul, if Paul had shown any sort of appreciation for Chimchar. Not necessarily trained it differently, but showed it appreciation.
This is quite a powerful scene in general, b/c Ash has to really care about what Chimchar thinks. And by that, I mean, as experienced as Ash is, many of the problems Ash has had with his pokemon in Sinnoh have been problems he's had before with other pokemon. Turtwig's stubborness, Buizel's pride are both issues he's dealt with before in other regions, and so he had really no worries that he could deal with that. Gliscor has been something different, but part of the comedy of that relationship is Ash never seeming to understand how much Gliscor wants to be used. It's funny, but not something serious. Ash's relationship with Chimchar is different; this is serious and meaningful, and goes beyond that of a pokemon and a trainer. Chimchar is almost like another human being. It's not the same type of friendly relationship Ash has with Pikachu, but I think it's deeper in a way. Chimchar's opinion of Ash means a great deal for Ash's character, and how he'll grow up. And Ash wants to be "grown up," although I don't mean he's a kid, b/c he isn't. But he wants to be somewhat like Cynthia. He's extremely eager, and it pops up a few times in this episodes, at very interesting pts. These scenes don't influence the main plot of the episode in any real way, but I think they are interesting. His decision to use Pikachu directly to attack Toxicroack (asking Dawn to cover him), his hastiness in chasing after TG even though Chimchar is injured, again wanting to get on the move w/o any news from Staravia (Cynthia urges him to calm down), and then near end of the episode, where he blames himself for TG's escape, punching his fist in frustration. The last one is the most interesting, in that Brock looks at him, but no one else says anything (which maybe points to a dubbing error). It's like a desire to prove himself, that's special in that no one else seems to share it, or makes any judgement about him for having it (there is one scene at the start of the episode where Cynthia's grandmother gives a compliment, but that was for both Ash and Dawn). And I don't get the feeling Ash is doing this to show off, either; this is his own expectation, although it seems unreasonable to maybe everyone else, even the viewer of the episode. Watching this episode, you wouldn't feel like Ash was a happy guy.
But Cynthia is someone a little different. Ash maybe is the character that's fun to watch for what feels like forever now, but Cynthia is the character I wish I could be like. Talk about confidence and elegance! When fighting TG, she states she has no problem showing off, and I get the feeling that's a truth. But that's pretty much the only thing she says that hints at what she's capable of (and she's capable of some pretty serious things; see what she does to Jupiter(hope I got the name right) later down the road-she's ruthless when she has to be); everything else she says is sweet and thoughtful. She enjoys being herself, and as stressful as her life must be, she doesn't show it at all. Ash (and probably the others too, but I've been talking mostly about Ash) is taken by surprise at the end of the episode when Cynthia receives a new challenge for her champion status. She says, to everyone-but I think it's fitting for Ash-, that it's important to live full lives, even though there are some bad things in the world. Seeing how obsessed Ash is in this episode with finding TG and proving his worth (to himself, I really think), I think he should really take this to heart. But, I don't think he really gets it. I'm not sure I really get it either, unfortunately.
Cynthia's words about Chimchar being the link b/w Ash and Paul are still a little unresolved, even now that we're into the next region. What Ash's and Paul's battle at the Sinnoh League really meant, I don't know. No one knows, to be honest. And like I've mentioned before, the transition to the next generation was quite abrupt. There were some scenes before and in that league battle that definitely were mysterious and need a little explaining, particularly from Paul's side. I think what Cynthia tells Chimchar in this episode is interesting, in that she, again, doesn't take a side. She tells Chimchar to remember that it's been though a lot, and been through alot with both Paul and Ash. I'm absolutely surmising here, but I wonder if she's indicating that Paul and Ash themselves have been through a good deal. We've watched Ash the whole way, so maybe that's a bit of a funny idea; I can think of only one scene that may support this, and that was in the Jhoto advertisement arc that comes up a pretty good deal later, where there's a really out-of-the-blue flashback about Ash as a child. For Paul, this idea is much more valid; there's a lot more to him than what's been revealed right now (although hinted at back at Reggie's display of his badges/frontier symbols). Even going to the end of Sinnoh, there's still a great deal about Paul that's not really settled.