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.
Looking back on it, I’m sure I was only capitalizing on what felt like a rare opportunity