And yet I was suddenly considering a city hall job. I’d winced at the pay cut, but on some visceral level I was just intrigued. I was feeling another twinge, a quiet nudge toward what might be a whole different future from the one I’d planned for. I was almost ready to leap, but for one thing. It wasn’t just about me anymore. When Valerie called me a few days later to follow up, I told her I was still thinking the offer over. I then asked a final and probably strange question. “Could I please,” I said, “also introduce you to my fiancé?”
* * *
I suppose I should back up here, rewinding us through the heavy heat of that summer, through the disorienting haze of those long months after my father died. Barack had flown back to Chicago to be with me for as long as he could around my dad’s funeral before returning to finish at Harvard. After graduation in late May, he packed up his things, sold his banana-yellow Datsun, and flew back to Chicago, delivering himself to 7436 South Euclid Avenue and into my arms. I loved him. I felt loved by him. We’d made it almost two years as a long-distance couple, and now, finally, we could be a short-distance couple. It meant that we once again had weekend hours to linger in bed, to read the newspaper and go out for brunch and share every thought we had. We could have Monday night dinners and Tuesday, Wednesday, and Thursday night dinners, too. We could shop for groceries and fold laundry in front of the TV. On the many evenings when I still got weepy over the loss of my dad, Barack was now there to curl himself around me and kiss the top of my head.
Barack was relieved to be done with law school, eager to get out of the abstract realm of academia and into work that felt more engaging and real. He’d also sold his idea for a nonfiction book about race and identity to a New York publisher, which for someone who worshipped books as he did felt like an enormous and humbling boon. He’d been given an advance and had about a year to complete the manuscript.
Barack had, as he always seemed to, plenty of options. His reputation—the gushing reports by his law school professors, the New York Times story about his selection as president of the Law Review—seemed to bring a flood of opportunity. The University of Chicago offered him an unpaid fellowship that came with a small office for the year, the idea being that he’d write his book there and maybe eventually sign on to teach as an adjunct professor at the law school. My colleagues at Sidley & Austin, still hoping Barack would come work full-time at the firm, provided him with a desk to use during the eight or so weeks leading up to his bar exam in July. He was now also considering taking a job at Davis, Miner, Barnhill & Galland, a small public interest firm that did civil rights and fair housing work and whose attorneys had been aligned closely with Harold Washington, which was a huge draw for Barack.
There’s something innately bolstering about a person who sees his opportunities as endless, who doesn’t waste time or energy questioning whether they will ever dry up. Barack had worked hard and dutifully for everything he was now being given, but he wasn’t notching achievements or measuring his progress against that of others, as so many people I knew did—as I sometimes did myself. He seemed, at times, beautifully oblivious to the giant rat race of life and all the material things a thirtysomething lawyer was supposed to be going after, from a car that wasn’t embarrassing to a house with a yard in the suburbs or a swank condo in the Loop. I’d observed this quality in him before, but now that we were living together and I was considering making the first real swerve of my life, I came to value it even more.
In a nutshell, Barack believed and trusted when others did not. He had a simple, buoying faith that if you stuck to your principles, things would work out. I’d had so many careful, sensible conversations at this point, with so many people, about how to extract myself from a career in which, by all outward measures, I was flourishing. Again and again, I’d read the caution and concern on so many faces when I spoke of having loans to pay off, of not yet having managed to buy a house. I couldn’t help but think about how my father had kept his aims deliberately modest, avoiding every risk in order to give us constancy at home. I still walked around with my mother’s advice ringing in my ear: Make the money first and worry about your happiness later. Compounding my anxiety was the one deep longing that far outmatched any material wish: I knew I wanted to have children, sooner rather than later. And how would that work if I abruptly started over in a brand-new field?
Barack, when he showed up back in Chicago, became a kind of soothing antidote. He absorbed my worries, listened as I ticked off every financial obligation I had, and affirmed that he, too, was excited to have children. He acknowledged that there was no way we could predict how exactly we’d manage things, given that neither of us wanted to be locked into the comfortable predictability of a lawyer’s life. But the bottom line was that we were far from poor and our future was promising, maybe even more promising for the fact that it couldn’t easily be planned.
His was the lone voice telling me to just go for it, to erase the worries and go toward whatever I thought would make me happy. It was okay to make my leap into the unknown, because—and this would count as startling news to most every member of the Shields/Robinson family, going back all the way to Dandy and Southside—the unknown wasn’t going to kill me.
Don’t worry, Barack was saying. You can do this. We’ll figure it out.
* * *
A word now about the bar exam: It’s a necessary chore, a rite of passage for any just-hatched lawyer wishing to practice, and though the content and structure of the test itself vary somewhat from state to state, the experience of taking it—a two-day, twelve-hour exam meant to prove your knowledge of everything from contract law to arcane rules about secured transactions—is pretty much universally recognized as hellish. Just as Barack was intending to, I had sat for the Illinois bar exam three years earlier, the summer after finishing up at Harvard, submitting myself beforehand to what was supposed to be a self-disciplined two months of logging hours as a first-year associate at Sidley while also taking a bar review class and pushing myself through a dauntingly fat book of practice tests.
This was the same summer that Craig was getting married to Janis in her hometown of Denver. Janis had asked me to be a bridesmaid, and for a whole set of reasons—not the least of which being that I’d just spent seven years grinding nonstop at Princeton and Harvard—I hurled myself, early and eagerly, into the role. I oohed and aahed at wedding dresses and helped plan the bachelorette activities. There was nothing I wouldn’t do to help make the anointed day merrier. I was far more excited about the prospect of my brother taking his wedding vows, in other words, than I was about reviewing what constituted a tort.
This was in the old days, back when test results arrived via the post office. That fall, with both the bar exam and the wedding behind me, I called my father from work one day and asked if he’d check to see if the mail had come in. It had. I asked if there was an envelope in there for me. There was. Was it a letter from the Illinois State Bar Association? Why, yes, that’s what it said on the envelope. I next asked if he’d open it for me, which is when I heard some rustling and then a long, damning pause on the other end of the line.
I had failed.
I had never in my entire life failed a test, unless you want to count the moment in kindergarten when I stood up in class and couldn’t read the word “white” off the manila card held by my teacher. But I’d blown it with the bar. I was ashamed, sure that I’d let down every person who’d ever taught, encouraged, or employed me. I wasn’t used to blundering. If anything, I generally overdid things, especially when it came to preparing for a big moment or test, but this one I’d let slip by. I think now that it was a by-product of the disinterest I’d felt all through law school, burned out as I was on being a student and bored by subjects that struck me as esoteric and far removed from real life. I wanted to be around people and not books, which is why the best part of law school for me had been volunteering at the school’s Legal Aid Bureau, where
I could help someone get a Social Security check or stand up to an out-of-line landlord.
But still, I didn’t like to fail. The sting of it would stay with me for months, even as plenty of my colleagues at Sidley confessed that they, too, hadn’t passed the bar exam the first time. Later that fall, I buckled down and studied for a do-over test, going on to pass it handily. In the end, aside from issues of pride, my screwup would make no difference at all.
Several years later, though, the memory was causing me to regard Barack with extra curiosity. He was attending bar review classes and carrying around his own bar review books, and yet didn’t seem to be cracking them as often as I thought maybe he should—as I would, anyway, knowing what I knew now. But I wasn’t going to nag him or even offer myself as an example of what could go wrong. We were built so differently, he and I. For one thing, Barack’s head was an overpacked suitcase of information, a mainframe from which he could seemingly pull disparate bits of data at will. I called him “the fact guy,” for how he seemed to have a statistic to match every little twist in a conversation. His memory seemed not-quite-but-almost photographic. The truth was, I wasn’t worried about whether he’d pass the bar and, somewhat annoyingly, neither was he.
So we celebrated early, on the very same day he finished the exam—July 31, 1991—booking ourselves a table at a downtown restaurant called Gordon. It was one of our favorite places, a special-occasion kind of joint, with soft Art Deco lighting and crisp white tablecloths and things like caviar and artichoke fritters on the menu. It was the height of summer and we were happy.
At Gordon, Barack and I always ordered every course. We had martinis and appetizers. We picked a nice wine to go with our entrées. We talked idly, contentedly, maybe a little sappily. As we were reaching the end of the meal, Barack smiled at me and raised the subject of marriage. He reached for my hand and said that as much as he loved me with his whole being, he still didn’t really see the point. Instantly, I felt the blood rise in my cheeks. It was like pushing a button in me—the kind of big blinking red button you might find in some sort of nuclear facility surrounded by warning signs and evacuation maps. Really? We were going to do this now?
In fact, we were. We’d had the hypothetical marriage discussion plenty of times already, and nothing much ever changed. I was a traditionalist and Barack was not. It seemed clear that neither one of us could be swayed. But still, this didn’t stop us—two lawyers, after all—from taking up the topic with hot gusto. Surrounded by men in sport coats and women in nice dresses enjoying their fancy meals, I did what I could to keep my voice calm.
“If we’re committed,” I said, as evenly as I could muster, “why wouldn’t we formalize that commitment? What part of your dignity would be sacrificed by that?”
From here, we traversed all the familiar loops of the old argument. Did marriage matter? Why did it matter? What was wrong with him? What was wrong with me? What kind of future did we have if we couldn’t sort this out? We weren’t fighting, but we were quarreling, and doing it attorney-style. We punched and counterpunched, dissected and cross-examined, though it was clearly I who was more inflamed. It was I who was doing most of the talking.
Eventually, our waiter came around holding a dessert plate, covered by a silver lid. He slid it in front of me and lifted the cover. I was almost too miffed to even look down, but when I did, I saw a dark velvet box where the chocolate cake was supposed to be. Inside it was a diamond ring.
Barack looked at me playfully. He’d baited me. It had all been a ruse. It took me a second to dismantle my anger and slide into joyful shock. He’d riled me up because this was the very last time he would invoke his inane marriage argument, ever again, as long as we both should live. The case was closed. He dropped to one knee then and with an emotional hitch in his voice asked sincerely if I’d please do him the honor of marrying him. Later, I’d learn that he’d already gone to both my mother and my brother to ask for their approval ahead of time. When I said yes, it seemed that every person in the whole restaurant started to clap.
For a full minute or two, I stared dumbfounded at the ring on my finger. I looked at Barack to confirm that this was all real. He was smiling. He’d completely surprised me. In a way, we’d both won. “Well,” he said lightly, “that should shut you up.”
* * *
I said yes to Barack, and shortly after that I said yes to Valerie Jarrett, accepting her offer to come work at city hall. Before committing, I made a point of following through on my request to introduce Barack and Valerie, scheduling a dinner during which the three of us could talk.
I did this for a couple of reasons. For one, I liked Valerie. I was impressed by her, and whether or not I ended up taking the job, I was excited to get to know her better. I knew that Barack would be impressed, too. More important, though, I wanted him to hear Valerie’s story. Like Barack, she’d spent part of her childhood in a different country—in her case, Iran, where her father had been a doctor at a hospital—and returned to the United States for her schooling, giving her the same kind of clear-eyed perspective I saw in Barack. Barack had concerns about my working at city hall. Like Valerie, he’d been inspired by the leadership of Harold Washington when he was mayor, but felt decidedly less affinity for the old-school establishment represented by Richard M. Daley. It was the community organizer in him: Even while Washington was in office, he’d had to battle relentlessly and sometimes fruitlessly with the city in order to get even the smallest bit of support for grassroots projects. Though he’d been nothing but encouraging about my job prospects, I think he was quietly worried I might end up disillusioned or disempowered working under Daley.
Valerie was the right person to address any concerns. She’d rearranged her entire life in order to work for Washington and then lost him almost immediately. The void that followed Washington’s death offered a kind of cautionary tale for the future, one I’d eventually find myself trying to explain to people across America: In Chicago, we’d made the mistake of putting all our hopes for reform on the shoulders of one person without building the political apparatus to support his vision. Voters, especially liberal and black voters, viewed Washington as a kind of golden savior, a symbol, the man who could change everything. He’d carried the load admirably, inspiring people like Barack and Valerie to move out of the private sector and into community work and public service. But when Harold Washington died, most of the energy he’d generated did, too.
Valerie’s decision to stay on with the mayor’s office had required some thought, but she explained to us why she felt it was the right choice. She described feeling supported by Daley and knowing that she was being useful to the city. Her loyalty, she said, had been to Harold Washington’s principles more than to the man himself. Inspiration on its own was shallow; you had to back it up with hard work. This idea resonated with both me and Barack, and inside that one dinner I felt as if something had been cemented: Valerie Jarrett was now a part of our lives. Without our ever discussing it, it seemed almost as if the three of us had somehow agreed to carry one another a good long way.
* * *
There was one last thing to do, now that we were engaged, now that I’d taken a new job and Barack had made a commitment to Davis, Miner, Barnhill & Galland, the public interest law firm that had been courting him: We took a vacation, or maybe more accurately we went on a sort of pilgrimage. We flew out of Chicago on a Wednesday in late August, had a long wait in the airport in Frankfurt, Germany, and then flew another eight hours to arrive in Nairobi just before dawn, stepping outside in the Kenyan moonlight and into what felt like a different world altogether.
I had been to Jamaica and the Bahamas, and to Europe a few times, but this was my first time being this far from home. I felt Nairobi’s foreignness—or really, my own foreignness in relation to it—immediately, even in the first strains of morning. It’s a sensation I’ve come to love as I’ve traveled more, the way a new place sign
als itself instantly and without pretense. The air has a different weight from what you’re used to; it carries smells you can’t quite identify, a faint whiff of wood smoke or diesel fuel, maybe, or the sweetness of something blooming in the trees. The same sun comes up, but looking slightly different from what you know.
Barack’s half sister Auma met us at the airport, greeting us both warmly. The two of them had met only a handful of times, beginning six years earlier when Auma had visited Chicago, but they had a close bond. Auma is a year older than Barack. Her mother, Grace Kezia, had been pregnant with Auma when Barack Obama Sr. left Nairobi to study in Hawaii in 1959. (They also had a son, Abongo, who was a toddler at the time.) After he returned to Kenya in the mid-1960s, Barack senior and Kezia went on to have two more children together.
Auma had ebony skin and brilliant white teeth and spoke with a strong British accent. Her smile was enormous and comforting. Arriving in Kenya, I was so tired from the travel I could barely make conversation, but riding into the city in the backseat of Auma’s rattletrap Volkswagen Bug, I took note of how the quickness of her smile was just like Barack’s, how the curve of her head also resembled his. Auma also clearly had inherited the family brains: She’d been raised in Kenya and returned there often, but she’d gone to college in Germany and was still living there, studying for a PhD. She was fluent in English, German, Swahili, and her family’s local language, called Luo. Like us, she was just here for a visit.
Auma had arranged for me and Barack to stay in a friend’s empty apartment, a spartan one-bedroom in a nondescript cinder-block building that had been painted bright pink. For the first couple of days, we were so zonked by jet lag it felt as if we were moving at half speed. Or maybe it was just the pace of Nairobi, which ran on an entirely different logic than Chicago did, its roads and British-style roundabouts clogged by a mix of pedestrians, bikers, cars, and matatus—the tottering, informal jitney-like buses that could be seen everywhere, painted brightly with murals and tributes to God, their roofs piled high with strapped-on luggage, so crowded that passengers sometimes just rode along, clinging precariously to the exterior.
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