You know he's just not cut out to be ruthless. (You know if you go to Pickham after the thing on Neos, you get Angelo saying something along the lines of, "Pickham is where people wind up when they haven't anywhere else to go, right? What? No, I'm not looking for anyone..." and then a bit about no matter how far "he" had fallen, he wouldn't go someplace like Pickham, anyway.)
Have I mentioned how much I love my boys and their fuckedup-itude?