neighborhood school didn’t run field trips there. If there were cultural events open to the community when I was a kid, my family hadn’t known about them. We had no friends—no acquaintances, even—who were students or alumni. The University of Chicago was an elite school, and to most everyone I knew growing up, elite meant not for us. Its gray stone buildings almost literally had their backs turned to the streets surrounding campus. Driving past, my dad used to roll his eyes at the flocks of students haplessly jaywalking across Ellis Avenue, wondering how it was that such smart people had never learned to properly cross a street.
Like many South Siders, my family maintained what was an admittedly dim and limited view of the university, even if my mom had passed a year happily working there. When it came time for me and Craig to think about college, we didn’t even consider applying to the University of Chicago. Princeton, for some strange reason, had struck us as more accessible.
Hearing all this, Art was incredulous. “You’ve really never been here?” he said. “Never?”
“Nope, not once.”
There was an odd power in saying it out loud. I hadn’t given the idea much thought before now, but it occurred to me that I’d have made a perfectly fine University of Chicago student, if only the town-gown divide hadn’t been so vast—if I’d known about the school and the school had known about me. Thinking about this, I felt an internal prick, a small subterranean twinge of purpose. The combination of where I came from and what I’d made of myself gave me a certain, possibly meaningful perspective. Being black and from the South Side, I suddenly saw, helped me recognize problems that a man like Art Sussman didn’t even realize existed.
In several years, I’d get my chance to work for the university and reckon with some of these community-relations problems directly, but right now Art was just kindly offering to pass around my résumé.
“I think you should talk to Susan Sher,” he told me then, unwittingly setting off what to this day feels like an inspired chain reaction. Susan was about fifteen years older than I was. She’d been a partner at a big law firm but had ultimately bailed out of the corporate world, just as I was hoping to do, though she was still practicing law with the Chicago city government. Susan had slate-gray eyes, the kind of fair skin that belongs on a Victorian queen, and a laugh that often ended with a mischievous snort. She was gently confident and highly accomplished and would become a lifelong friend. “I’d hire you right now,” she told me when we finally met. “But you just finished telling me how you don’t want to be a lawyer.”
Instead, Susan proposed what now seems like another fated introduction, steering me and my résumé toward a new colleague of hers at city hall—another ship-jumping corporate lawyer with a yen for public service, this one a fellow daughter of the South Side and someone who would end up altering my course in life, not once, but repeatedly. “The person you really need to meet,” Susan said, “is Valerie Jarrett.”
Valerie Jarrett was the newly appointed deputy chief of staff to the mayor of Chicago and had deep connections across the city’s African American community. Like Susan, she’d been smart enough to land herself a job in a blue-chip firm after law school and had then been self-aware enough to realize that she wanted out. She’d moved to city hall largely because she was inspired by Harold Washington, who’d been elected mayor in 1983 when I was away at college and was the first African American to hold the office. Washington was a voluble politician with an exuberant spirit. My parents loved him for how he could pepper an otherwise folksy speech with Shakespeare quotes and for the famous, mouth-stuffing vigor with which he ate fried chicken at community events on the South Side. Most important, he had a distaste for the entrenched Democratic machinery that had long governed Chicago, awarding lucrative city contracts to political donors and generally keeping blacks in service to the party but rarely allowing them to advance into official elected roles.
Building his campaign around reforming the city’s political system and better tending to its neglected neighborhoods, Washington won the election by a hair. His style was brassy and his temperament was bold. He was able