Obama was looking forward to spending the night at his house in Kenwood, on the city’s South Side—the redbrick Georgian Revival pile that he and Michelle and their daughters left behind when they took up residence in the White House. He arrived fairly late, after 10:00 p.m., but then stayed up even later, intrigued by some old boxes that had belonged to his late mother, Ann Dunham. Dunham had died seven years earlier, but Obama hadn’t sorted through all her things. Now, alone in his old house for just the third night since he’d become president, he started rummaging through...