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