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 to eviscerate opponents with his eloquence and intellect. He was a black, brainy superhero. He clashed regularly and fearlessly with the mostly white old-guard members of the city council and was viewed as something of a walking legend, especially among the city’s black citizens, who saw his leadership as kindling a larger spirit of progressivism. His vision had been an early inspiration for Barack, who arrived in Chicago to work as an organizer in 1985.
Valerie, too, was drawn by Washington. She was thirty years old when she joined Washington’s staff in 1987, at the start of his second term. She was also the mother of a young daughter and soon to be divorced, which made it a deeply inconvenient time to take the sort of pay cut one does when leaving a swishy law firm and landing in city government. And within months of her starting the job, tragedy struck: Harold Washington abruptly had a heart attack and died at his desk, thirty minutes after holding a press conference about low-income housing. In the aftermath, a black alderman was appointed by the city council to take Washington’s place, but his tenure was relatively short. In a move many African Americans saw as a swift and demoralizing return to the old white ways of Chicago politics, voters went on to elect Richard M. Daley, the son of a previous mayor, Richard J. Daley, who was broadly considered the godfather of Chicago’s famous cronyism.
Though she had reservations about the new administration, Valerie had decided to stay on at city hall, moving out of the legal department and directly into Mayor Daley’s office. She was glad to be there, as much for the contrast as anything. She described to me how her transition from corporate law into government felt like a relief, an energizing leap out of the super-groomed unreality of high-class law being practiced on the top floors of skyscrapers and into the real world—the very real world.
Chicago’s City Hall and County Building is a flat-roofed, eleven-story, gray-granite monolith that occupies an entire block between Clark and LaSalle north of the Loop. Compared with the soaring office towers surrounding it, it’s squatty but not without grandeur, featuring tall Corinthian columns out front and giant, echoing lobbies made primarily of marble. The county runs its business out of the east-facing half of the building; the city uses the western half, which houses the mayor and city council members as well as the city clerk. City hall, as I learned on the sweltering summer day I showed up to meet Valerie for a job interview, was both alarmingly and upliftingly packed with people.
There were couples getting married and people registering cars. There were people lodging complaints about potholes, their landlords, their sewer lines, and everything else they felt the city could improve. There were babies in strollers and old ladies in wheelchairs. There were journalists and lobbyists, and also homeless people just looking to get out of the heat. Out on the sidewalk in front of the building, a knot of activists waved signs and shouted chants, though I can’t remember what it was they were angry about. What I do know is that I was simultaneously taken aback and completely enthralled by the clunky, controlled chaos of the place. City hall belonged to the people. It had a noisy, gritty immediacy that I never felt at Sidley.
Valerie had reserved twenty minutes on her schedule to talk to me that day, but our conversation ended up stretching for an hour and a half. A thin, light-skinned African American woman dressed in a beautifully tailored suit, she was soft-spoken and strikingly serene, with a steady brown-eyed gaze and an impressive grasp of how the city functioned. She enjoyed her job but didn’t try to gloss over the bureaucratic headaches of government work. Something about her caused me instantly to relax. Years later, Valerie would tell me that to her surprise I’d managed to reverse the standard interview process on her that day—that I’d given her some basic, helpful information about myself, but otherwise I’d grilled her, wanting to understand every last feeling she had about the work she did and how responsive the mayor was to his employees. I was testing the suitability of the work for me as much as she was testing the suitability of me for the work.