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I love all the beautiful Imperial Sithy-Wan art. It's not my cup of tea for reading but I do understand the appeal. But when I do find myself thinking of Sithy-Wan it goes very grungy.
Maybe he's more of a dark Jedi because he's not a Sith he's just fallen.
Obi-Wan is a person that survives and outlives so for me his breaking point is grimy dirty losing again and surviving it, surviving another person. It's not even a person he knew long or well but they were good and they didn't deserve it.
He loses hope and himself.
So you have Vader getting news of him and it's this angry Obi-Wan who has traveled and has been killing 'bad' people without mercy and without compassion to them or himself.
And he's the Obi-Wan that can look at Vader and say: "This time it will be through your heart, Anakin."