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Barack Obama was late on day one. I sat in my office on the forty-seventh floor, waiting and not waiting for him to arrive. Like most first-year lawyers, I was busy. I put in long hours at Sidley & Austin, often eating both lunch and dinner at my desk while combating a continuous flow of documents, all of them written in precise and decorous lawyer-language. I read memos, I wrote memos, I edited other people’s memos. At this point, I thought of myself basically as trilingual. I knew the relaxed patois of the South Side and the high-minded diction of the Ivy League, and now on top of that I spoke Lawyer, too. I’d been hired into the firm’s marketing and intellectual property practice group, which was considered internally more freewheeling and creative than other groups, I suppose because we dealt at least some of the time with advertising. Part of my job involved poring over scripts for our clients’ TV and radio ads, making sure they didn’t violate Federal Communications Commission standards. I would later be awarded the honor of looking after the legal concerns of Barney the Dinosaur. (Yes, this is what passes for freewheeling in a law firm.) The problem for me was that as a junior associate my work didn’t involve much actual interaction with clients and I was a Robinson, raised in the boisterous scrum of my extended family, molded by my father’s instinctive love of a crowd. I craved interaction of any sort. To offset the solitude, I joked around with Lorraine, my assistant, a hyperorganized, good-humored African American woman several years my senior who sat just outside my office and answered my phone. I had friendly professional relationships with some of the senior partners and perked up at any chance I had to chitchat with my fellow associates, but in general everyone was overloaded with work and careful not to waste one billable minute of the day. Which put me back at my desk, alone with my documents.
If I had to spend seventy hours a week somewhere, my office was a pleasant enough place. I had a leather chair, a buffed walnut desk, and wide windows with a southeastern view. I could look out over the hodgepodge of the business district and see the white-capped waves of Lake Michigan, which in summertime were dotted with bright sailboats. If I angled myself a certain way, I could trace the coastline and glimpse a narrow seam of the South Side with its low-rise rooftops and intermittent stands of trees. From where I sat, the neighborhoods appeared placid and almost toylike, but the reality was in many cases far different. Parts of the South Side had become desolate as businesses shut down and families continued to move out. The steel mills that had once provided stability were cutting thousands of jobs. The crack epidemic, which had ravaged African American communities in places like Detroit and New York, was only just reaching Chicago, but its course was no less destructive. Gangs battled for market share, recruiting young boys to run their street-corner operations, which, while dangerous, was far more lucrative than going to school. The city’s murder rate was starting to tick upward—a sign of even more trouble to come.
I made good money at Sidley but was pragmatic enough to take a bird in the hand when it came to housing. Since finishing law school, I’d been living back in my old South Shore neighborhood, which was still relatively untouched by gangs and drugs. My parents had moved downstairs into Robbie and Terry’s old space, and at their invitation I’d taken over the upstairs apartment, where we’d lived when I was a kid, sprucing it up with a crisp white couch and framed batik prints on the walls. I wrote my parents an occasional check that loosely covered my share of the utilities. It hardly counted as paying rent, but they insisted it was plenty. Though my apartment had a private entrance, I most often tromped through the downstairs kitchen as I came and went from work—in part because my parents’ back door opened directly to the garage and in part because I was still and always would be a Robinson. Even if I now fancied myself the sort of suit-wearing, Saab-driving independent young professional I’d always dreamed of being, I didn’t much like being alone. I fortified myself with daily check-ins with my mom and dad. I’d hugged them that very morning, in fact, before dashing out the door and driving through a heavy rainstorm to get to work. To get to work, I might add, on time.
I looked at my watch.
“Any sign of this guy?” I called to Lorraine.
Her sigh was audible. “Girl, no,” she called back. She was amused, I could tell. She knew how tardiness drove me nuts—how I saw it as nothing but hubris.
Barack Obama had already created a stir at the firm. For one thing, he’d just finished his first year of law school, and normally we only hired second-year students for summer positions. But rumor had it he was exceptional. Word had spread that one of his professors at Harvard—the daughter of a managing partner—claimed he was the most gifted law student she’d ever encountered. Some of the secretaries who’d seen the guy come in for his interview were saying that on top of this apparent brilliance he was also cute.
I was skeptical of all of it. In my experience, you put a suit on any half-intelligent black man and white people tended to go bonkers. I was doubtful he’d earned the hype. I’d checked out his photo in the summer edition of our staff directory—a less-than-flattering, poorly lit head shot of a guy with a big smile and a whiff of geekiness—and remained unmoved. His bio said he was originally from Hawaii, which at least made him a comparatively exotic geek. Otherwise, nothing stood out. The only surprise had come weeks earlier when I made a quick obligatory phone call to introduce myself. I’d been pleasantly startled by the voice on the other end of the line—a rich, even sexy, baritone that didn’t seem to match his photo one bit.
It was another ten minutes before he checked in at the reception area on our floor and I walked out to meet him, finding him seated on a couch—one Barack Obama, dressed in a dark suit and still a little damp from the rain. He grinned sheepishly and apologized for his lateness as he shook my hand. He had a wide smile and was taller and thinner than I’d imagined he’d be—a man who was clearly not much of an eater, who also looked fully unaccustomed to wearing business clothes. If he knew he was arriving with a whiz-kid reputation, it didn’t show. As I walked him through the corridors to my office, introducing him to the cushy mundanities of corporate law—showing him the word-processing center and the coffee machine, explaining our system for tracking billable hours—he was quiet and deferential, listening attentively. After about twenty minutes, I delivered him to the senior partner who’d be his actual supervisor for the summer and went back to my desk.
Later that day, I took Barack to lunch at the fancy restaurant on the first floor of our office building, a place packed with well-groomed bankers and lawyers power lunching over meals priced like dinners. This was the boon of having a summer associate to advise: It was an excuse to eat out and eat well, and 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 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.
Twenty minutes later, I caught sight of Barack across the room, in the grips of what looked to be an endless conversation with the woman, who was doing a large portion of the talking. He shot me a look, implying that he’d like to be rescued. But he was a grown man. I let him rescue himself.
“Do you know what she asked me?” he said the next day, turning up in my office, still slightly incredulous. “She asked if I liked to go riding. She meant on horseback.” He said they’d discussed their favorite movies, which also hadn’t gone well.
Barack was cerebral, probably too cerebral for most people to put up with. (This, in fact, would be my friend’s assessment of him when we next spoke.) He wasn’t a happy-hour guy, and maybe I should have realized that earlier. My world was filled with hopeful, hardworking people who were obsessed with their own upward mobility. They had new cars and were buying their first condos and liked to talk about it all over martinis after work. Barack was more content to spend an evening alone, reading up on urban housing policy. As an organizer, he’d spent weeks and months listening to poor people describe their challenges. His insistence on hope and the potential for mobility, I was coming to see, came from an entirely different and not easily accessible place.
There was a time, he told me, when he’d been looser, more wild. He’d spent the first twenty years of his life going by the nickname Barry. As a teen, he smoked pot in the lush volcanic foothills of Oahu. At Occidental, he rode the waning energy of the 1970s, embracing Hendrix and the Stones. Somewhere along the way, though, he’d stepped into the fullness of his birth name—Barack Hussein Obama—and the complicated rubric of his identity. He was white and black, African and American. He was modest and lived modestly, yet knew the richness of his own mind and the world of privilege that would open up to him as a result. He took it all seriously, I could tell. He could be lighthearted and jokey, but he never strayed far from a larger sense of obligation. He was on some sort of quest, though he didn’t yet know where it would lead. All I knew was that it didn’t translate over drinks. Next time happy hour rolled around, I left him at the office.
When I was a kid, my parents smoked. They lit cigarettes in the evenings as they sat in the kitchen, talking through their workdays. They smoked while they cleaned the dinner dishes later at night, sometimes opening a window to let in some fresh air. They weren’t heavy smokers, but they were habitual smokers, and defiant ones, too. They smoked long after the research made clear that it was bad for you.
The whole thing drove me crazy, and Craig as well. We made an elaborate show of coughing when they lit up. We ran sabotage missions on their supplies. When Craig and I were very young, we pulled a brand-new carton of Newports from a shelf and set about destroying them, snapping them like beans over the kitchen sink. Another time, we dipped the ends of their cigarettes in hot sauce and returned them to the pack. We lectured our parents about lung cancer, explaining the horrors that had been shown to us on filmstrips during health class at school—images of smokers’ lungs, desiccated and black as charcoal, death in the making, death right inside your chest. For contrast, we’d been shown pictures of florid pink lungs that were healthy, uncontaminated by smoke. The paradigm was simple enough to make their behavior confounding: Good/Bad. Healthy/Sick. You choose your own future. It was everything our parents had ever taught us. And yet it would be years before they finally quit.
Barack smoked the way my parents did—after meals, walking down a city block, or when he was feeling anxious and needed to do something with his hands. In 1989, smoking was more prevalent than it is now, more embedded in everyday life. Research on the effects of secondhand smoke was relatively new. People smoked in restaurants, offices, and airports. But still, I’d seen the filmstrips. To me, and to every sensible person I knew, smoking was pure self-destruction.
Barack knew exactly how I felt about it. Our friendship was built on a plainspoken candor that I think we both enjoyed.
“Why would someone as smart as you do something as dumb as that?” I’d blurted on the very first day we met, watching him cap off our lunch with a smoke. It was an honest question.
As I recall, he just shrugged, acknowledging that I was right. There was no fight to be put up, no finer point to be argued. Smoking was the one topic where Barack’s logic seemed to leave him altogether.
Whether I was going to admit it or not, though, something between us had started to change. On days when we were too busy to check in face-to-face, I found myself wondering what he’d been up to. I talked myself out of being disappointed when he didn’t surface in my office doorway. I talked myself out of being too excited when he did. I had feelings for the guy, but they were latent, buried deep beneath my resolve to keep my life and career tidy and forward focused—free from any drama. My annual reviews at work were solid. I was on track to become an equity partner at Sidley & Austin, probably before I hit thirty-two. It was everything I wanted—or so I was trying to convince myself.
I might have been ignoring whatever was growing between us, but he wasn’t.
“I think we should go out,” Barack announced one afternoon as we sat finishing a meal.
“What, you and me?” I feigned shock that he even considered it a possibility. “I told you, I don’t date. And I’m your adviser.”
He gave a wry laugh. “Like that counts for anything. You’re not my boss,” he said. “And you’re pretty cute.”
Barack had a smile that seemed to stretch the whole width of his face. He was a deadly combination of smooth and reasonable. More than once in the coming days, he laid out the evidence for why we should be going out. We were compatible. We made each other laugh. We were both available, and furthermore we confessed to being almost immediately uninterested in anyone else we met. Nobody at the firm, he argued, would care if we dated. In fact, maybe it would be seen as a positive. He presumed that the partners wanted him to come work for them, eventually. If he and I were an item, it would improve the odds of his committing.
“You mean I’m like some sort of bait?” I said, laughing. “You flatter yourself.”
Over the course of the summer, the firm organized a series of events and outings for its associates, sending around sign-up sheets for anyone who wanted to go. One was a weeknight performance of Les Misérables at a theater not far from the office. I put us on the list for two tickets, which was standard behavior for a junior-associate adviser and her summer-associate charge. We were supposed to be attending firm functions together. I was supposed to be ensuring that his experience with Sidley & Austin was bright and positive. That was the whole point.
We sat side by side in the theater, both of us worn out after a long day of work. The curtain went up and the singing began, giving us a gray, gloomy version of Paris. I don’t know if it was my mood or whether it was just Les Misérables itself, but I spent the next hour feeling helplessly pounded by French misery. Grunts and chains. Poverty and rape. Injustice and oppression. Millions of people around the world had fallen in love with this musical, but I squirmed in my seat, trying to rise above the inexplicable torment I felt every time the melody repeated.
When the lights went up for intermission, I stole a glance at Barack. He was slumped down, with his right elbow on the armrest and index finger resting on his forehead, his expression unreadable.
“What’d you think?” I said.
He gave me a sideways look. “Horrible, right?”
I laughed, relieved that he felt the same way.
Barack sat up in his seat. “What if we got out of here?” he said. “We could just leave.”
Under normal circumstances, I wouldn’t bolt. I wasn’t that sort of person. I cared too much what the other lawyers thought of me—what they’d think if they spotted our empty seats. I cared too much, in general, about finishing what I’d started, about seeing every last little thing through to the absolute heart-stopping end, even if it was an overwrought Broadway musical on an otherwise beautiful Wednesday night. This, unfortunately, was the box checker in me. I endured misery for the sake of appearances. But now, it seemed, I’d joined up with someone who did not.
Avoiding everyone we knew from work—the other advisers and their summer associates bubbling effusively in the lobby—we slipped out of the theater and into a balmy evening. The last light was draining from a purple sky. I exhaled, my relief so palpable that it caused Barack to laugh.
“Where are we going now?” I asked.
“How ’bout we grab a drink?”
We walked to a nearby bar in the same manner we always seemed to walk, with me a step forward and him a step back. Barack was an ambler. He moved with a loose-jointed Hawaiian casualness, never given to hurry, even and especially when instructed to hurry. I, on the other hand, power walked even during my leisure hours and had a hard time decelerating. But I remember how that night I counseled myself to slow down, just a little—just enough so that I could hear what he was saying, because it was beginning to dawn on me that I cared about hearing everything he said.
Until now, I’d constructed my existence carefully, tucking and folding every loose and disorderly bit of it, as if building some tight and airless piece of origami. I had labored over its creation. I was proud of how it looked. But it was delicate. If one corner came untucked, I might discover that I was restless. If another popped loose, it might reveal I was uncertain about the professional path I’d so deliberately put myself on, about all the things I told myself I wanted. I think now it’s why I guarded myself so carefully, why I still wasn’t ready to let him in. He was like a wind that threatened to unsettle everything.
A day or two later, Barack asked if I could give him a ride to a barbecue for summer associates, which was happening that weekend at a senior partner’s home in one of the wealthy lakefront suburbs north of the city. The weather, as I remember it, was clear that day, the lake sparkling at the edge of a well-tended lawn. A caterer served food as music blared over stereo speakers and people remarked on the tasteful grandeur of the house. The whole milieu was a portrait of affluence and ease, a less-than-subtle reminder of the payoff that came when you committed yourself wholeheartedly to the grind. Barack, I knew, wrestled with what he wanted to do with his life, which direction his career would take. He had an uneasy relationship with wealth. Like me, he’d never had it, and he didn’t aspire to it, either. He wanted to be effective far more than he wanted to be rich but was still trying to figure out how.
We walked through the party not quite like a couple but still mostly together, drifting between clusters of colleagues, drinking beer and lemonade, eating hamburgers and potato salad from plastic plates. We’d get separated and then find each other again. It all felt natural. He was quietly flirty with me and I was flirty back. Some of the men started playing pickup basketball, and I watched as Barack moseyed on over to the court in his flip-flops to join. He had an easy rapport with everyone at the firm. He addressed all the secretaries by name and got along with everyone—from the older, stuffier lawyers to the ambitious young bucks who were now playing basketball. He’s a good person, I thought to myself, watching him pass the ball to another lawyer.
Having sat through scores of high school and college games, I recognized a good player when I saw one, and Barack quickly passed the test. He played an athletic, artful form of basketball, his lanky body moving quickly, showing power I hadn’t before noticed. He was swift and graceful, even in his Hawaiian footwear. I stood there pretending to listen to what somebody’s perfectly nice wife was saying to me, but my eyes stayed fixed on Barack. I was struck for the first time by the spectacle of him—this strange mix-of-everything man.
As we drove back to the city in the early evening, I felt a new ache, some freshly planted seed of longing. It was July. Barack would be leaving sometime in August, disappearing into law school and whatever else life held for him there. Nothing had changed outwardly—we were kidding around, as we always did, gossiping about who’d said what at the barbecue—but there was a certain kind of heat climbing my spine. I was acutely aware of his body in the small space of my car—his elbow resting on the console, his knee within reach of my hand. As we followed the southward curve of Lake Shore Drive, passing bicyclists and runners on the pedestrian pathways, I was arguing silently with myself. Was there a way to do this unseriously? How badly could it hurt my job? I had no clarity about anything—about what was proper, about who would find out and whether that mattered—but it hit me that I was done waiting for clarity.
He was living in Hyde Park, subletting an apartment from a friend. By the time we pulled into the neighborhood, the tension lay thick in the air between us, like something inevitable or predestined was finally about to happen. Or was I imagining it? Maybe I’d shut him down too many times. Maybe he’d given up and now just saw me as a good, stalwart friend—a girl with an air-conditioned Saab who’d drive him around when he needed it.
I halted the car in front of his building, my mind still in blurry overdrive. We let an awkward beat pass, each waiting for the other to initiate a good-bye. Barack cocked his head at me.
“Should we get some ice cream?” he said.
This is when I knew the game was on, one of the few times I decided to stop thinking and just live. It was a warm summer evening in the city that I loved. The air felt soft on my skin. There was a Baskin-Robbins on the block near Barack’s apartment, and we got ourselves two cones, taking them outside to eat, finding ourselves a spot on the curb. We sat close together with our knees pulled up, pleasantly tired after a day spent outdoors, eating our ice cream quickly and wordlessly, trying to stay ahead of the melt. Maybe Barack read it on my face or sensed it in my posture—the fact that everything for me had now begun to loosen and unfold.
He was looking at me curiously, with the trace of a smile.
“Can I kiss you?” he asked.
And with that, I leaned in and everything felt clear.
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