"Many have said that part of the appeal of “Dreams” is its honesty, pointing out that it was written at a time when Obama had no idea that he would run for office. In fact, Obama had been talking about a political career for years, musing about becoming mayor or governor. According to a recent biography of Obama by the Chicago Tribune reporter David Mendell, he even told his future brother-in-law, Craig Robinson, that he might run for President one day. (Robinson teased him, saying, “Yeah, yeah, okay, come over and meet my Aunt Gracie—and don’t tell anybody that!”) Obama was writing “Dreams” at the moment that he was preparing for a life in politics, and he launched his book and his first political campaign simultaneously, in the summer of 1995, when he saw his first chance of winning."

Ryan Lizza on Obama's Chicago roots at The New Yorker.