I know when I first thought about a brilliant judicial mind capable of dispensing wisdom for the ages the first person to come to mind was Kagan...
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And why do all his “brilliant” choices, always include someone with some sort of suspected “deviant or criminal” behavior? Or maybe it’s just birds of a feather flock together. I have a theory he chooses thusly so he can blackmail them later on into following his game plan, or risk exposure. (Massa comes to mind, but there are lots of others I am sure he has “the goods” on in other ways.)