3. Taking Winterfell
A classic case of a character getting in over their head, Theon thought that, somehow, he could take and hold Winterfell. Naturally, this leads to a whole bunch of problems and increasingly bad decisions, including the murder of a few poor orphans and Ser Rodrik. He really seems to be asking for it. His sister, Yara, shows up and offers to bail him out, but he arrogantly declines her offer. Honestly though, I cant help but feel bad for Theon. The world of Westeros is different from our own, and their concepts of family and honor are much stronger and bigger presences in their world. Put yourself in Theons shoes; just a boy, heir to the throne of a group of people following a completely different ideology found within the rest of Westeros. He is then taken away and held as a hostage for ten years by his enemies. They treat him nicely though, and over time he becomes fond of a few of them, despite being reminded constantly of his situation. This creates a metric ton of daddy issues and mixed signals, all of which is worsened when he returns home and finds out that his family doesnt even seem to want anything to do with him. Again, I cant help but feel sorry for the guy. He makes many mistakes, but given the context of the world he lives in, you understand how he could make these awful decisions. I truly do feel bad for the guy, however terrible of a human being he may be at times.