Alastair
You know, if I had feeling they might be hurt right now.
But, I'm a demon. Demon's don't have feelings. John was supposed to be the one who broke, but he got out because Azazel was a little sloppy.
There was a job to be done, Ruby. The first seal bad to be broken, and it was my job to do it. I was just getting it done... And having a little bit of... Fun with Dean afterwards.
You realize that... He was the first righteous man to actually enjoy the blade? I let him take up apprenticeship. I let him cut, and slice, and grow...