to do it on the firm’s expense account. As Barack’s adviser, I was meant to act as a
social conduit more than anything. My assignment was to make sure he was
happy in the job, that he had someone to come to if he needed advice, and that
he felt connected to the larger team. It was the start of a larger wooing process—
the idea being, as it was with all summer associates, that the firm might want to
recruit him for a full-time job once he had his law degree.
Very quickly, I realized that Barack would need little in the way of advice.
He was three years older than I was—about to turn twenty-eight. Unlike me,
he’d worked for several years after finishing his undergrad degree at Columbia
before moving on to law school. What struck me was how assured he seemed of
his own direction in life. He was oddly free from doubt, though at first glance it
was hard to understand why. Compared with my own lockstep march toward
success, the direct arrow shot of my trajectory from Princeton to Harvard to my
desk on the forty-seventh floor, Barack’s path was an improvisational zigzag
through disparate worlds. I learned over lunch that he was in every sense a hybrid
—the son of a black Kenyan father and a white mother from Kansas whose
marriage had been both youthful and short-lived. He’d been born and raised in
Honolulu but had spent four years of his childhood flying kites and catching
crickets in Indonesia. After high school, he’d passed two relatively laid-back years
as a student at Occidental College in Los Angeles before transferring to
Columbia, where by his own account he’d behaved nothing like a college boy set
loose in 1980s Manhattan and instead lived like a sixteenth-century mountain
hermit, reading lofty works of literature and philosophy in a grimy apartment on
109th Street, writing bad poetry, and fasting on Sundays.
We laughed about all of it, swapping stories about our backgrounds and
what led us to the law. Barack was serious without being self-serious. He was
breezy in his manner but powerful in his mind. It was a strange, stirring
combination. Surprising to me, too, was how well he knew Chicago.
Barack was the first person I’d met at Sidley who had spent time in the
barbershops, barbecue joints, and Bible-thumping black parishes of the Far South
Side. Before going to law school, he’d worked in Chicago for three years as a
community organizer, earning $12,000 a year from a nonprofit that bound
together a coalition of churches. His task was to help rebuild neighborhoods and
bring back jobs. As he described it, it had been two parts frustration to one part
reward: He’d spend weeks planning a community meeting, only to have a dozen
people show up. His efforts were scoffed at by union leaders and picked apart by
black folks and white folks alike. Yet over time, he’d won a few incremental