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 victories, and this seemed to encourage him. He was in law school, he explained, because grassroots organizing had shown him that meaningful societal change required not just the work of the people on the ground but stronger policies and governmental action as well.
Despite my resistance to the hype that had preceded him, I found myself admiring Barack for both his self-assuredness and his earnest demeanor. He was refreshing, unconventional, and weirdly elegant. Not once, though, did I think about him as someone I’d want to date. For one thing, I was his mentor at the firm. I’d also recently sworn off dating altogether, too consumed with work to put any effort into it. And finally, appallingly, at the end of lunch Barack lit a cigarette, which would have been enough to snuff any interest, if I’d had any to begin with.
He would be, I thought to myself, a good summer mentee.
* * *
Over the next couple of weeks, we fell into a kind of routine. In the late afternoon, Barack would wander down the hall and flop onto one of the chairs in my office, as if he’d known me for years. Sometimes it felt as if he had. Our banter was easy, our mind-sets alike. We gave each other sideways glances when people around us got stressed to the point of mania, when partners made comments that seemed condescending or out of touch. What was unspoken but obvious was that he was a brother, and in our office, which employed more than four hundred lawyers, only about five full-time attorneys were African American. Our pull toward each other was evident and easy to understand.
Barack bore no resemblance to the typical eager-beaver summer associate （as I myself had been two years earlier at Sidley）， networking furiously and anxiously wondering whether a golden-ticket job offer was coming. He sauntered around with calm detachment, which seemed only to increase his appeal. Inside the firm, his reputation was continuing to grow. Already, he was being asked to sit in on high-level partner meetings. Already, he was being pressed to give input on whatever issues were under discussion. At some point early in the summer, he pumped out a thirty-page memo about corporate governance that was evidently so thorough and cogent it became instantly legendary. Who was this guy? Everyone seemed intrigued.
“I brought you a copy,” Barack said one day, sliding his memo across my desk with a smile.
“Thanks,” I said, taking the file. “Looking forward to it.”
After he left, I tucked it into a drawer.
Did he know I’d never read it? I think he probably did. He’d given it to me half as a joke. We were in different specialty groups, so there was no material overlap in our work anyway. I had plenty of my own documents to contend with. And I didn’t need to be wowed. We were friends now, Barack and I, comrades in arms. We ate lunch out at least once a week and sometimes more often than that, always, of course, billing Sidley & Austin for the pleasure. Gradually, we learned more about each other. He knew that I lived in the same house as my parents, that my happiest memories of Harvard Law School stemmed from the work I’d done in the Legal Aid Bureau. I knew that he consumed volumes of political philosophy as if it were beach reading, that he spent all his spare change on books. I knew that his father had died in a car crash in Kenya and that he’d made a trip there to try to understand more about the man. I knew he loved basketball, went for long runs on the weekends, and spoke wistfully of his friends and family on Oahu. I knew he’d had plenty of girlfriends in the past, but didn’t have one now.
This last bit was something I thought I could rectify. My life in Chicago was nothing if not crowded with accomplished and eligible black women. My marathon work hours notwithstanding, I liked to socialize. I had friends from Sidley, friends from high school, friends developed through professional networking, and friends I’d met through Craig, who was newly married and making his living as an investment banker in town. We were a merry co-ed crew, congregating when we could in one downtown bar or another and catching up over long, lavish meals on weekends. I’d gone out with a couple of guys in law school but hadn’t met anyone special upon returning to Chicago and had little interest anyway. I’d announced to everyone, including potential suitors, that my career was my priority. I did, though, have plenty of girlfriends who were looking for someone to date.
One evening early in the summer, I brought Barack along with me to a happy hour at a downtown bar, which served as an unofficial monthly mixer for black professionals and was where I often met up with friends. He’d changed out of his work clothes, I noticed, and was wearing a white linen blazer that looked as if it’d come straight out of the Miami Vice costume closet. Ah well.
There was no arguing with the fact that even with his challenged sense of style, Barack was a catch. He was good-looking, poised, and successful. He was athletic, interesting, and kind. What more could anyone want? I sailed into the bar, certain I was doing everyone a favor—him and all the ladies. Almost immediately, he was corralled by an acquaintance of mine, a beautiful and high-powered woman who worked in finance. She perked up instantly, I could see, talking to Barack. Pleased with this development, I got myself a drink and moved on toward others I knew in the crowd.