Main to Supporting back to Main?

[Kenshin5]

Out of all the companions, will we ever see any of them as part of the main cast again?

I can see Misty return as part of the main cast. I really didn't think she got adequate closure when she left the group. It seemed more forced on her by her sisters leaving the gym then her willingly leaving. I think if she got the chance to travel again she would take it.

I could see Max rejoin only if they made progression with Ash character, then I could see an older Max join with Ralts as his signature poke. I'd like to see Max have his own adventures along with Ash adventures maybe his goal would be too become a Gym Leader like his father.

 

[Charicific]

You know, I know this is ridiculous but I always thought Ash will (at some point) beat the Champions League of each region he visited, I stress especially on Sinnoh since he made a promise himself, he wanna battle and beat Cynthia. Anyway as I said, I imagine Ash , going back to Kanto and head for the Champions League Challenge, Same happens with Johto, Hoenn, and Sinnoh...So at that specific time, I believe his old friends are gonna make a comeback to rejoin him in his new journey. For an instance, Misty lives in Kanto, so if ash head for the Kanto E4, Misty will be his companion since she is the representative of that region, it will be May rejoining him at Hoenn, and Dawn at Sinnoh. I sometimes think they might mix it up, maybe put May and Misty, Dawn and May...I dunno just mix his old friends...Of course I can dream about all that right? xD

 

[Kenshin5]

Cynthia does have a house in Undella Town that the main character battles with her at. So I wouldn't rule the possibility of this match up coming to fruition.

The only way I can see him go back to previous regions is if they run through the current Saga and have ample time to do a filler Saga like Orange Islands and Battle Frontier. The reason I say this is when a new generation comes out they would want to focus on that generation region so if he was going back to previous regions it would detract from that.

I think if they did do a League, Ash would have to take the Pokemon League Admissions Exam, instead of going around battling the gym leaders. That would seem to be tedious and take quite awhile.

If they do rejoin him I think they would have to work them into a new Saga with some other new companions.

 

[Mew~]

I actually have to admit I can see the whole supporting cast eventually meeting up with Ash at sometime in a different region at some point in the future. Obviously not all together. I just don't understand why we can't see at least one old supporting character with Ash and a new character from the games, I think that would balance the fandom out.

But yeah, let's go through it shall we. Misty, like you mentioned would probably jump at the chance to leave the gym and travel about again, since she was pretty much forced to position.
I could see Max joining Ash pretty soon too. I'd love it if the wirtes did something crazy and assuming hopefully that the R/S/E remakes come somewhat after the anime has finnished the Unova region, then I'd love it if they could somehow implement a way to get Max a little older and start a journey, maybe even making Ash older too or maybe letting Max start his journey early, I mean seriously, he already went through a load of stuff with Ash, May and Brock. So yeah, they could maybe get Max in with Ash at maybe a filler arc or something like that.
I don't see Brock returning for quite a while, since hes been along with Ash the longest if I can remember. But yeah, that doesn't mean he can't have his specials or cameos, even some mentions.
As for May and Dawn, who knows. It is a little complicated though, which I should I mentioned for Max too but- Since they're both from different regions than Ash, there may not be a bigger chance they bump into each other than like a character like Misty or Brock since they don't live that very much far apart if you ask me. But yeah, May and Max did get into Kanto with Professor Birch, and May did enter the wallace cup - so who knows, eh.
I wouldn't be that mad if they did some random stuff like Ash, Iris and Max. Or Ash, Dent and Misty... or Ash, Iris, Dent and Max. The list goes on, but it's easy to picture it. I think Max would find Iris really fun.

I'm starting to rethink Meowth going back to Team Rocket now though, but I wonder how they'll handle him.

 

[Charicific]

Let me clarify that a comeback during Unova is too hard, barely possible. Most obvious reason is the far distance to Unova, so if one of Ash's Companion is gonna visit, it must be a good reason other than saying "Hi".
For other reasons's well....May is busy in Johto, Dawn just headed to the Hoenn Grand Festival, And Misty in charge of the gym, I still don't understand howcome Misty is working there permenantly? Didn't I see her sisters with her in some episode she met Ash again?

Cynthia appearing in the game in Undella Town kinda keeps me positive, I just hope the same thing happens with Ash cuz you know not everything in-game happens in the anime so..

And as I said, Companions he met can come back if he went back challenging the champions league of every region, however as I claimed too, that is unlikely, its hard for me to see how would the writers are gonna handle such retract.

Lets not forget the fact that Pokemon always reset after every series, they are not gonna break this money making adventure so soon....

 

[Mew~]

Let me clarify that a comeback during Unova is too hard, barely possible. Most obvious reason is the far distance to Unova, so if one of Ash's Companion is gonna visit, it must be a good reason other than saying "Hi".
For other reasons's well....May is busy in Johto, Dawn just headed to the Hoenn Grand Festival, And Misty in charge of the gym, I still don't understand howcome Misty is working there permenantly? Didn't I see her sisters with her in some episode she met Ash again?

Misty still had her cameo whilst being gym leader and going to meet up with Ash in Hoenn for that togepi thingee. And May for the Wallace cup, whilst still being in the johto contests. So I wouldn't go as far as saying barely possible.

Cynthia appearing in the game in Undella Town kinda keeps me positive, I just hope the same thing happens with Ash cuz you know not everything in-game happens in the anime so..

Heh, if we do see a filler arc in east unova, then I can see an appearance happening. Though, it's not like we saw Oak in Johto or Eterna City. But who knows.

Lets not forget the fact that Pokemon always reset after every series, they are not gonna break this money making adventure so soon....

If your talking about the anime then I could just mention Johto, though I do see where your coming from with the games, n' such.

Either way, I still stick by my points, even though those comments weren't addressed to me, I still like to butt into these speculations. :3

 

[Charicific]

Misty still had her cameo whilst being gym leader and going to meet up with Ash in Hoenn for that togepi thingee. And May for the Wallace cup, whilst still being in the johto contests. So I wouldn't go as far as saying barely possible.

You do realize I was talking about Unova right?

 

[2Cool4Mewtwo]

The whole Eastern Unova is more than ample amount of space to temporarily bring in some older characters. But with huge gap of fillers between Castelia and Nimbasa... there could be no room for them if the show finishes at Opelucid City. I'm certainly not hoping it to be that way though. I think it would only make sense to bring some older characters back if they want to satisfy wider array of fans. (but producers are probably not going that way)

 

[Mew~]

You do realize I was talking about Unova right?

Urg, if you read through my reply, I was replying to what you said about it being barely possible for them to get to unova. The writers would implement a way like they did with May and Misty's cameos...