>>3115452He wasn't really that detestable until his plans to take Winterfell were underway. God it was gut wrenching when the horror of what he's doing first starts to set in for him, and he doubles down on trying to play the role of his Greyjoy forebearers only to realize more and more that he wanted to be a Stark, but it's too late, and h just keeps trying to adapt only for his schemes to make things worse thanks to the influence of Ramsay.
It was crushing. The general cockiness before all that was just a scared boy trying to be brave, and trying to figure out where he belongs. Once he's Reek we get a better look at a gentler more sensitive soul underneath all that, and one that is still so much stronger than anyone appreciated. Ramsay cowed him but he never truly broke him. Ramsay only destroyed the lies Theon was living, and now though maimed he can rise from the death of his ego. We all know the prayer of the Drowned God, right?
I do wish he'd taken the black, though, when he had the chance. Jon could have used a talented and cunning ally, because Jon is a little to pure and honorable for the politics of the Watch and Stannis' war. But Theon didn't give Jon enough credit, he didn't expect him to be capable of forgiving what he'd done. I loved how J.R.Martin drives the point about what might have been home with Jon saying he didn't believe Theon would kill his brothers, and also thinking to himself about what a great ranger Theon would have made. Damn if that didn't make me love Jon even more. The two best boys in the series, with Tyrion following close behind. (shame Tyrion as such a shit in a Dance with Dragons. He was my pick for best boy in the first three books, no matter how ugly he is)