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One day in 1995, Barack Obama went to see his alderman, an influential politician named Toni Preckwinkle, on Chicago’s South Side, where politics had been upended by scandal. Mel Reynolds, a local congressman, was facing charges of sexual assault of a sixteen-year-old campaign volunteer. (He eventually resigned his seat.) The looming vacancy set off a fury of ambition and hustle; several politicians, including a state senator named Alice Palmer, an education expert of modest political skills, prepared to enter the congressional race. Palmer represented Hyde Park—Obama’s neighborhood, a racially integrated, liberal sanctuary—and, if she ran for Congress, she would need a replacement in Springfield, the state capital. Obama at the time was a thirty-three-year-old lawyer, university lecturer, and aspiring office-seeker, and the Palmer seat was what he had in mind when he visited Alderman Preckwinkle.
“Barack came to me and said, ‘If Alice decides she wants to run, I want to run for her State Senate seat,’ ” Preckwinkle told me. We were in her district office, above a bank on a street of check-cashing shops and vacant lots north of Hyde Park. Preckwinkle soon became an Obama loyalist, and she stuck with him in a State Senate campaign that strained or ruptured many friendships but was ultimately successful. Four years later, in 2000, she backed Obama in a doomed congressional campaign against a local icon, the former Black Panther Bobby Rush. And in 2004 Preckwinkle supported Ob...