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.