What did President Barack Obama mean when he called empathy an "essential ingredient" in judicial decision making and, thus, the outstanding quality he would look for in his Supreme Court nominees? This article attempts to answer that question by an analysis of Obama’s public statements and published writing. It also provides a comparative study of Obama’s jurisprudence of empathy with Founding Era Justice James Wilson’s jurisprudence of common sense in order to illustrate the dangers of a judge deciding difficult cases with recourse to unconventional, extra-legal tools.