I’m so glad you asked me this, because this is something I’ve been meaning to talk about for a while. [There are spoilers for Theon’s sample chapter in TWOW from here on out!]
This is really more like wishful thinking than an actual theory. GRRM is an expert at destroying our expectations, so it’s really hard to predict what will happen to the characters, but this is what I hope will happen to Theon in TWOW.
This probably sounds crazy, but I really want Theon to go to Braavos. And here are my reasons for this:
1. According to the sample chapter, we know that Justin Massey is heading to Braavos to conduct business for Stannis, and that he wants to take Asha with him. Stannis seems to be against his wishes concerning Asha, but it’s possible that Justin could find some way to free her and take her with him anyway.
2. If Justin does manage to take Asha with him, I like to think that Asha would try convincing him to rescue Theon as well (if Theon is still alive at this point). Justin’s a pretty ambiguous character and it’s hard to tell where he stands exactly, but I think he would save Asha’s brother if she asked him to.
3. So let’s pretend that everything goes according to plan. Away to Braavos! I think a completely new setting would be really good for Theon, especially a setting that’s far removed from Westeros. He’s come so far after his Reek experience and I want to see him get his strength back so he can finally be somebody, and a foreign land would be a good place for him to do this. Half of Theon’s life has consisted of struggling between two cultures, after all, and being in a place like Braavos would help him let go of all that. He could start over and rebuild himself.
4. It would be really unwise for Theon to stay in Westeros anyway. If Stannis doesn’t kill him, then somebody else surely will, since everyone and his mom thinks he should die for being a “kinslayer” and a turncloak. He probably shouldn’t return home, either, since he’s really in no position to take the Seastone Chair. He might have the strongest claim, but he doesn’t have the physical or mental strength to take the chair from Euron, and even if he did manage to take it, the ironborn wouldn’t accept him in the post-torture state that he’s in.
5. There’s also the fact that Arya’s in Braavos. She’s all by herself and thinks she lost her whole family, so it would be interesting if somebody from her past at Winterfell showed up. Plus, the fact that Theon had to pretend that Jeyne Poole was Arya so she could marry Ramsay. I’d love to see him meet back up with the real Arya!
6. Braavos would be a good place for Asha as well. She’d be back on the water, but without the antics of her crazy uncles screwing everything up, and maybe she and Theon could finally build a normal sibling relationship.
7. There’s also the fact that I’m really fond of Braavos in general. It’s definitely my favorite setting outside of Westeros!
So there it is. All my crazy hopes and dreams! Hopefully GRRM doesn’t crush them too badly.