How Will This Go Down on the Show?
The show kept Bran and Rickon together for much longer than the books. They traveled all the way to the Wall together. So Theon’s squire (someone we’ve never seen in the show) following Rickon and Osha all the way to the Wall and then to Skagos seems unlikely. Stannis is dead and Davos hasn’t been to White Harbor, so that’s got to change. And Rickon and Osha would have to be idiots to willingly go to Skagos. There’s going to be some major changes on the show, for sure.
Let’s assume Rickon and Osha went to the Last Hearth. Sam had a chance to talk with Bran as he left for Beyond the Wall. Maybe Bran told Sam where Rickon was heading, and Sam told Jon. Once Jon is back up and running, he could send Ser Davos (who’s sort of stuck in the North at the moment without any close allies) to the Last Hearth for them. Or maybe Jon just sends Davos on a diplomatic mission to the Last Hearth, and Davos happens across Rickon and Osha.
But that wouldn’t be all that exciting, especially since in the books it sounds like Davos will have to brave a bunch of cannibals and unicorns to get Rickon and Osha back. So how could Osha and Rickon end up at Skagos? Well, let’s remember, traveling in Westeros is extremely dangerous (unless you’re Littlefinger). So isn’t it possible that Rickon and Osha were kidnapped and taken to Skagos? Ser Davos would be in a position to find out about it, since he knows some unsavory seafaring folks, and could go to Skagos to save them, possibly even to put himself in Jon’s (or the Boltons’) good graces.
Why Rickon Matters in Season 6
Rickon is a Stark, if he is in danger or taken hostage, he could be used as leverage over Jon or Sansa or any of the Northern Lords. Anyone who finds him could use him as a political pawn and base a campaign to reclaim the North in his name. This might be especially important for Jon, since it would let him unite the North in the Stark name without having to be a Stark himself (although that could change). Whoever has control of Rickon has a claim on the North, and it could spell disaster if he fell into the wrong hands (like, oh, say the Boltons’).
The show already hinted at this when the Boltons sent their man to the Wall in case Bran tried to contact Jon. Bran killed him using Hodor, but one of the Stark boys almost ended up in Bolton clutches already. If Rickon did he would be much easier to keep under control than Sansa was, especially if they killed Osha, which they probably would. So we better hope Jon or Sansa reaches Rickon before the Boltons do. Both groups are on the look out for them. We can only hope that there is a Stark back in Winterfell soon, and that it isn’t in a dungeon.
Game of Thrones returns April 24th, and Rickon and Osha will be back in Season 6.