Please feel free to delete my commentary, I won’t be offended. I’m pretty sure this has been said a thousand times before but I’m having a lot of Killian Jones feels today and they wouldn’t really fit in the tags.
Losing people and betrayal have been huge motivating factors in Killian Jones’ life. From the very beginning he had very few people who he genuinely cared for and who cared for him. His father abandoned him but he did have his brother, Liam. He became a lieutenant and an honourabe man. But Liam was all he had and when he died that loss, and the betrayal of his sovereign, motivated Killian to take on a life of piracy.
Finding and loving Milah didn’t change that. She didn’t inspire him to become a better version of himself, he remained a pirate. It was her death that changed him and, unfortunately, not for the better. Once again he lost the only thing that he had, the only person who really cared for him and the only person that he truly loved. He went from a pirate to a man motivated by vengeance, someone willing to hurt anyone that got in his way.
When Baelfire turned up in his life, Killian said that he was willing to change and I believe him. He would have given up his pursuit of revenge in order to raise the boy. Because Killian Jones wanted a home and a family; he wanted to change. Because deep down he is a man of honour (just one that lost his way). Killian’s reaction to Baelfire’s rejection is not justifiable but I think it is understandable. When Bae refused to stay Killian clung on to the only thing he had left, his revenge, and turned Bae over to Pan. It’s the same thing he does when he loses Emma 300 years later.
Fast forward hundreds of years and Killian Jones does change, and “all it took was meeting the right person” - Emma Swan. In Tallahassee we see a Killian Jones who, although still hell bent on revenge, is willing to work with the good guys and turn his back on Cora. He had no intention of betraying Emma until she betrayed him. And his behaviour throughout the rest of season 2 is a direct result of that. He may steal the magic bean in the finale but his conscience, and his memory of Bae, get in the way. He realises that he can change, he can care for someone again and that someone is Emma Swan.
He turned his back on revenge and became the man of honour, the hero, he used to be from that point on. He did that without any promises from Emma, he did it because she inspired him to. And this time, when he loses someone important to him, he tries desperately to go back to his previous life, he tries to revert just like he’d done in the past. Only, this time, it doesn’t work. He can’t go back to the man he used to be. Emma changes him for the better, even when there is no hope of him ever seeing her again.
Everything he does in the Jolly Roger flashbacks reeks of desperation. He’s trying to fix the hole that Emma left in his heart the same way that he always has. He betrays Ariel, he ‘kills’ Blackbeard, he clings onto the Jolly Roger…but it’s all in vain. Ultimately, Emma Swan changed Hook irrevocably, in a way that nobody else in his life was able to do. That’s what makes their relationship so wonderful (to me), because I think he does exactly the same for her too.