When Obama and I sat down together in the spring of 2015 at the annual dinner for the White House Correspondents' Assn., during my term as the organization's president, I asked him why he waded into such knotty matters where people were unlikely to be moved. He looked at me with an almost confused smile, like he couldn't imagine what I was suggesting. One of his closest aides had his own theory in a private conversation we had shortly after.