I don't think Orin Kerr quite gets what Obama means when he says he wants a judge with "empathy". Susan Bandes gives a good rundown of what "empathy" means in this context. The short version is that empathy is the ability to understand exactly how adopting a given legal rule or doctrine will effect litigants and those like them now and in the future.
Empathy isn't something a judge either has or doesn't have. It's a skill, and like most skills it runs on a continuum. The ability to place yourself in the shoes of another and try and imagine what their life will be like if you rule a certain way is difficult, and not everyone has that ability (to the requisite degree we want in a judge). Yet this skill often goes to the heart of the legal function. Far from being "lawless", trying to remove empathy from judging would, I believe, exile law from law.