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PART ONE

THE BET

CHAPTER 1

OF ALL THE ROOMS and halls and landmarks that make up the White House and its grounds, it was the West Colonnade that I loved best.

For eight years that walkway would frame my day, a minute-long, open-air commute from home to office and back again. It was where each morning I felt the first slap of winter wind or pulse of summer heat; the place where I’d gather my thoughts, ticking through the meetings that lay ahead, preparing arguments for skeptical members of Congress or anxious constituents, girding myself for this decision or that slow-rolling crisis.

In the earliest days of the White House, the executive offices and the First Family’s residence fit under one roof, and the West Colonnade was little more than a path to the horse stables. But when Teddy Roosevelt came into office, he determined that a single building couldn’t accommodate a modern staff, six boisterous children, and his sanity. He ordered construction of what would become the West Wing and Oval Office, and over decades and successive presidencies, the colonnade’s current configuration emerged: a bracket to the Rose Garden north and west—the thick wall on the north side, mute and unadorned save for high half-moon windows; the stately white columns on the west side, like an honor guard assuring safe passage.

As a general rule, I’m a slow walker—a Hawaiian walk, Michelle likes to say, sometimes with a hint of impatience. I walked differently, though, on the colonnade, conscious of the history that had been made there and those who had preceded me. My stride got longer, my steps a bit brisker, my footfall on stone echoed by the Secret Service detail trailing me a few yards back. When I reached the ramp at the end of the colonnade (a legacy of FDR and his wheelchair—I picture him smiling, chin out, cigarette holder clenched tight in his teeth as he strains to roll up the incline), I’d wave at the uniformed guard just inside the glass-paned door. Sometimes the guard would be holding back a surprised flock of visitors. If I had time, I would shake their hands and ask where they were from. Usually, though, I just turned left, following the outer wall of the Cabinet Room and slipping into the side door by the Oval Office, where I greeted my personal staff, grabbed my schedule and a cup of hot tea, and started the business of the day.

Several times a week, I would step out onto the colonnade to find the groundskeepers, all employees of the National Park Service, working in the Rose Garden. They were older men, mostly, dressed in green khaki uniforms, sometimes matched with a floppy hat to block the sun, or a bulky coat against the cold. If I wasn’t running late, I might stop to compliment them on the fresh plantings or ask about the damage done by the previous night’s storm, and they’d explain their work with quiet pride. They were men of few words; even with one another they made their points with a gesture or a nod, each of them focused on his individual task but all of them moving with synchronized grace. One of the oldest was Ed Thomas, a tall, wiry Black man with sunken cheeks who had worked at the White House for forty years. The first time I met him, he reached into his back pocket for a cloth to wipe off the dirt before shaking my hand. His hand, thick with veins and knots like the roots of a tree, engulfed mine. I asked how much longer he intended to stay at the White House before taking his retirement.

“I don’t know, Mr. President,” he said. “I like to work. Getting a little hard on the joints. But I reckon I might stay long as you’re here. Make sure the garden looks good.” Oh, how good that garden looked! The shady magnolias rising high at each corner; the hedges, thick and rich green; the crab apple trees pruned just so. And the flowers, cultivated in greenhouses a few miles away, providing a constant explosion of color—reds and yellows and pinks and purples; in spring, the tulips massed in bunches, their heads tilted toward the sun; in summer, lavender heliotrope and geraniums and lilies; in fall, chrysanthemums and daisies and wildflowers. And always a few roses, red mostly but sometimes yellow or white, each one flush in its bloom.

Each time I walked down the colonnade or looked out the window of the Oval Office, I saw the handiwork of the men and women who worked outside. They reminded me of the small Norman Rockwell painting I kept on the wall, next to the portrait of George Washington and above the bust of Dr. King: five tiny figures of varying skin tones, workingmen in dungarees, hoisted up by ropes into a crisp blue sky to polish the lamp of Lady Liberty. The men in the painting, the groundskeepers in the garden—they were guardians, I thought, the quiet priests of a good and solemn order. And I would tell myself that I needed to work as hard and take as much care in my job as they did in theirs.

With time, my walks down the colonnade would accumulate with memories. There were the big public events, of course—announcements made before a phalanx of cameras, press conferences with foreign leaders. But there were also the moments few others saw—Malia and Sasha racing each other to greet me on a surprise afternoon visit, or our dogs, Bo and Sunny, bounding through the snow, their paws sinking so deep that their chins were bearded white. Tossing footballs on a bright fall day, or comforting an aide after a personal hardship.

Such images would often flash through my mind, interrupting whatever calculations were occupying me. They reminded me of time passing, sometimes filling me with longing—a desire to turn back the clock and begin again. This wasn’t possible on my morning walk, for time’s arrow moved only forward then; the day’s work beckoned; I needed to focus on only those things to come.

The night was different. On the evening walk back to the residence, my briefcase stuffed with papers, I would try to slow myself down, sometimes even stop. I’d breathe air laced with the scent of soil and grass and pollen, and listen to the wind or the patter of rain. I sometimes stared at the light against the columns, and the regal mass of the White House, its flag aloft on the roof, lit bright, or I’d look toward the Washington Monument piercing the black sky in the distance, occasionally catching sight of the moon and stars above it, or the twinkling of a passing jet.

In moments like these, I would wonder at the strange path—and the idea—that had brought me to this place.

I DON’T COME from a political family. My maternal grandparents were midwesterners from mostly Scots-Irish stock. They would have been considered liberal, especially by the standards of the Depression-era Kansas towns they were born in, and they were diligent about keeping up with the news. “It’s part of being a well-informed citizen,” my grandmother, whom we all called Toot (short for Tutu, or Grandma, in Hawaiian), would tell me, peering over the top of her morning Honolulu Advertiser. But she and my grandfather had no firm ideological or partisan leanings to speak of, beyond what they considered to be common sense. They thought about work—my grandmother was vice president of escrow at one of the local banks, my grandfather a life insurance salesman—and paying the bills, and the small diversions that life had to offer.

And anyway, they lived on Oahu, where nothing seemed that urgent. After years spent in places as disparate as Oklahoma, Texas, and Washington State, they’d finally moved to Hawaii in 1960, a year after its statehood was established. A big ocean now separated them from riots and protests and other such things. The only political conversation I can recall my grandparents having while I was growing up had to do with a beachside bar: Honolulu’s mayor had torn down Gramps’s favorite watering hole in order to renovate the beachfront at the far end of Waikiki.

Gramps never forgave him for it.

My mother, Ann Dunham, was different, full of strong opinions. My grandparents’ only child, she rebelled against convention in high school—reading beatnik poets and French existentialists, joyriding with a friend to San Francisco for days without telling anyone. As a kid, I’d hear from her about civil rights marches, and why the Vietnam War was a misguided disaster; about the women’s movement (yes on equal pay, not as keen on not shaving her legs) and the War on Poverty. When we moved to Indonesia to live with my stepfather, she made sure to explain the sins of government corruption (“It’s just stealing, Barry”), even if everyone appeared to be doing it. Later, during the summer I turned twelve, when we went on a month-long family vacation traveling across the United States, she insisted we watch the Watergate hearings every night, providing her own running commentary (“What do you expect from a McCarthyite?”).

She didn’t just focus on headlines either. Once, when she discovered I had been part of a group that was teasing a kid at school, she sat me down in front of her, lips pursed with disappointment.

“You know, Barry,” she said (that’s the nickname she and my grandparents used for me when I was growing up, often shortened to “Bar,” pronounced “Bear”), “there are people in the world who think only about themselves. They don’t care what happens to other people so long as they get what they want. They put other people down to make themselves feel important.

“Then there are people who do the opposite, who are able to imagine how others must feel, and make sure that they don’t do things that hurt people.

“So,” she said, looking me squarely in the eye. “Which kind of person do you want to be?”

I felt lousy. As she intended it to, her question stayed with me for a long time.

For my mother, the world was full of opportunities for moral instruction. But I never knew her to get involved in a political campaign. Like my grandparents, she was suspicious of platforms, doctrines, absolutes, preferring to express her values on a smaller canvas. “The world is complicated, Bar. That’s why it’s interesting.” Dismayed by the war in Southeast Asia, she’d end up spending most of her life there, absorbing the language and culture, setting up micro-lending programs for people in poverty long before micro-credit became trendy in international development. Appalled by racism, she would marry outside her race not once but twice, and go on to lavish what seemed like an inexhaustible love on her two brown children. Incensed by societal constraints put upon women, she’d divorce both men when they proved overbearing or disappointing, carving out a career of her own choosing, raising her kids according to her own standards of decency, and pretty much doing whatever she damn well pleased.

In my mother’s world, the personal really was political—although she wouldn’t have had much use for the slogan.

None of this is to say that she lacked ambition for her son. Despite the financial strain, she and my grandparents would send me to Punahou, Hawaii’s top prep school. The thought of me not going to college was never entertained. But no one in my family would ever have suggested I might hold public office someday. If you’d asked my mother, she might have imagined that I’d end up heading a philanthropic institution like the Ford Foundation. My grandparents would have loved to see me become a judge, or a great courtroom lawyer like Perry Mason.

“Might as well put that smart mouth of his to use,” Gramps would say.

Since I didn’t know my father, he didn’t have much input. I vaguely understood that he had worked for the Kenyan government for a time, and when I was ten, he traveled from Kenya to stay with us for a month in Honolulu. That was the first and last I saw of him; after that, I heard from him only through the occasional letter, written on thin blue airmail paper that was preprinted to fold and address without an envelope. “Your mother tells me you think you may want to study architecture,” one letter might read. “I think this is a very practical profession, and one that can be practiced anywhere in the world.” It was not much to go on.

As for the world beyond my family—well, what they would see for most of my teenage years was not a budding leader but rather a lackadaisical student, a passionate basketball player of limited talent, and an incessant, dedicated partyer. No student government for me; no Eagle Scouts or interning at the local congressman’s office. Through high school, my friends and I didn’t discuss much beyond sports, girls, music, and plans for getting loaded.

Three of these guys—Bobby Titcomb, Greg Orme, and Mike Ramos—remain some of my closest friends. To this day, we can laugh for hours over stories of our misspent youth. In later years, they would throw themselves into my campaigns with a loyalty for which I will always be grateful, becoming as skilled at defending my record as anyone on MSNBC.

But there were also times during my presidency—after they had watched me speak to a big crowd, say, or receive a series of crisp salutes from young Marines during a base tour—when their faces would betray a certain bafflement, as if they were trying to reconcile the graying man in a suit and tie with the ill-defined man-child they’d once known.

That guy? they must have said to themselves. How the hell did that happen?

And if my friends had ever asked me directly, I’m not sure I’d have had a good answer.

I DO KNOW that sometime in high school I started asking questions—about my father’s absence and my mother’s choices; about how it was I’d come to live in a place where few people looked like me. A lot of the questions centered on race: Why did Blacks play professional basketball but not coach it? What did that girl from school mean when she said she didn’t think of me as Black? Why were all the Black men in action movies switchblade-wielding lunatics except for maybe the one decent Black guy—the sidekick, of course—who always seemed to end up getting killed?

But I wasn’t concerned only with race. It was class as well. Growing up in Indonesia, I’d seen the yawning chasm between the lives of wealthy elites and impoverished masses. I had a nascent awareness of the tribal tensions in my father’s country—the hatred that could exist between those who on the surface might look the same. I bore daily witness to the seemingly cramped lives of my grandparents, the disappointments they filled with TV and liquor and sometimes a new appliance or car. I noticed that my mother paid for her intellectual freedom with chronic financial struggles and occasional personal chaos, and I became attuned to the not-so-subtle hierarchies among my prep school classmates, mostly having to do with how much money their parents had. And then there was the unsettling fact that, despite whatever my mother might claim, the bullies, cheats, and self-promoters seemed to be doing quite well, while those she considered good and decent people seemed to get screwed an awful lot.

All of this pulled me in different directions. It was as if, because of the very strangeness of my heritage and the worlds I straddled, I was from everywhere and nowhere at once, a combination of ill-fitting parts, like a platypus or some imaginary beast, confined to a fragile habitat, unsure of where I belonged. And I sensed, without fully understanding why or how, that unless I could stitch my life together and situate myself along some firm axis, I might end up in some basic way living my life alone.

I didn’t talk to anyone about this, certainly not my friends or family. I didn’t want to hurt their feelings or stand out more than I already did. But I did find refuge in books. The reading habit was my mother’s doing, instilled early in my childhood—her go-to move anytime I complained of boredom, or when she couldn’t afford to send me to the international school in Indonesia, or when I had to accompany her to the office because she didn’t have a babysitter.

Go read a book, she would say. Then come back and tell me something you learned.

There were a few years when I lived with my grandparents in Hawaii while my mother continued her work in Indonesia and raised my younger sister, Maya. Without my mother around to nag me, I didn’t learn as much, as my grades readily attested. Then, around tenth grade, that changed. I still remember going with my grandparents to a rummage sale at the Central Union Church, across the street from our apartment, and finding myself in front of a bin of old hardcover books. For some reason, I started pulling out titles that appealed to me, or sounded vaguely familiar—books by Ralph Ellison and Langston Hughes, Robert Penn Warren and Dostoyevsky, D. H. Lawrence and Ralph Waldo Emerson. Gramps, who was eyeing a set of used golf clubs, gave me a confused look when I walked up with my box of books.

“Planning to open a library?”

My grandmother shushed him, finding my sudden interest in literature admirable. Ever practical, she did suggest I might want to focus on my class assignments before digging into Crime and Punishment.

I ended up reading all those books, sometimes late, after I got home from basketball practice and a six-pack with my friends, sometimes after bodysurfing on a Saturday afternoon, sitting alone in Gramps’s rickety old Ford Granada with a towel around my waist to avoid getting the upholstery wet. When I finished with the first set of books, I went to other rummage sales, looking for more. Much of what I read I only dimly understood; I took to circling unfamiliar words to look up in the dictionary, although I was less scrupulous about decoding pronunciations—deep into my twenties I would know the meaning of words I couldn’t pronounce. There was no system to this, no rhyme or pattern. I was like a young tinkerer in my parents’ garage, gathering up old cathode-ray tubes and bolts and loose wires, not sure what I’d do with any of it, but convinced it would prove handy once I figured out the nature of my calling.

MY INTEREST IN books probably explains why I not only survived high school but arrived at Occidental College in 1979 with a thin but passable knowledge of political issues and a series of half-baked opinions that I’d toss out during late-night bull sessions in the dorm.

Looking back, it’s embarrassing to recognize the degree to which my intellectual curiosity those first two years of college paralleled the interests of various women I was attempting to get to know: Marx and Marcuse so I had something to say to the long-legged socialist who lived in my dorm; Fanon and Gwendolyn Brooks for the smooth-skinned sociology major who never gave me a second look; Foucault and Woolf for the ethereal bisexual who wore mostly black. As a strategy for picking up girls, my pseudo-intellectualism proved mostly worthless; I found myself in a series of affectionate but chaste friendships.

Still, these halting efforts served a purpose: Something approaching a worldview took shape in my mind. I was helped along by a handful of professors who tolerated my iffy study habits and my youthful pretensions. I was helped even more by a handful of mostly older students—Black kids from the inner city, white kids who had scratched their way into college from small towns, first-generation Latino kids, international students from Pakistan or India or countries in Africa that teetered on the edge of chaos. They knew what mattered to them; when they spoke in class, their views were rooted in actual communities, actual struggles. Here’s what these budget cuts mean in my neighborhood. Let me tell you about my school before you complain about affirmative action. The First Amendment is great, but why does the U.S. government say nothing about the political prisoners in my country?

The two years I spent at Occidental represented the start of my political awakening. But that didn’t mean I believed in politics. With few exceptions, everything I observed about politicians seemed dubious: the blow-dried hair, the wolfish grins, the bromides and self-peddling on TV while behind closed doors they curried the favor of corporations and other monied interests. They were actors in a rigged game, I decided, and I wanted no part of it.

What did capture my attention was something broader and less conventional—not political campaigns but social movements, where ordinary people joined together to make change. I became a student of the suffragists and early labor organizers; of Gandhi and Lech Wałesa and the African National Congress. Most of all I was inspired by the young leaders of the civil rights movement—not just Dr. King but John Lewis and Bob Moses, Fannie Lou Hamer and Diane Nash. In their heroic efforts—going door-to-door to register voters, sitting down at lunch counters, and marching to freedom songs—I saw the possibility of practicing the values my mother had taught me; how you could build power not by putting others down but by lifting them up. This was true democracy at work—democracy not as a gift from on high, or a division of spoils between interest groups, but rather democracy that was earned, the work of everybody. The result was not just a change in material conditions but a sense of dignity for people and communities, a bond between those who had once seemed far apart.

This, I decided, was an ideal worth pursuing. I just needed focus. After my sophomore year I transferred to Columbia University, figuring it would be a new start. For three years in New York, holed up in a series of dilapidated apartments, largely shorn of old friends and bad habits, I lived like a monk—reading, writing, filling up journals, rarely bothering with college parties or even eating hot meals. I got lost in my head, preoccupied with questions that seemed to layer themselves one over the next. What made some movements succeed where others failed? Was it a sign of success when portions of a cause were absorbed by conventional politics, or was it a sign that the cause had been hijacked? When was compromise acceptable and when was it selling out, and how did one know the difference?

Oh, how earnest I was then—how fierce and humorless! When I look back on my journal entries from this time, I feel a great affection for the young man that I was, aching to make a mark on the world, wanting to be a part of something grand and idealistic, which evidence seemed to indicate did not exist. This was America in the early 1980s, after all. The social movements of the previous decade had lost their vibrancy. A new conservatism was taking hold. Ronald Reagan was president; the economy was in recession; the Cold War was in full swing.

If I were to travel back in time, I might urge the young man I was to set the books aside for a minute, open the windows, and let in some fresh air (my smoking habit was then in full bloom). I’d tell him to relax, go meet some people, and enjoy the pleasures that life reserves for those in their twenties. The few friends I had in New York tried to offer similar advice.

“You need to lighten up, Barack.”

“You need to get laid.”

“You’re so idealistic. It’s great, but I don’t know if what you’re saying is really possible.”

I resisted these voices. I resisted precisely because I feared they were right. Whatever I was incubating during those hours spent alone, whatever vision for a better world I’d let flourish in the hothouse of my youthful mind, it could hardly withstand even a simple conversational road test. In the gray light of a Manhattan winter and against the overarching cynicism of the times, my ideas, spoken aloud in class or over coffee with friends, came off as fanciful and far-fetched. And I knew it. In fact, it’s one of the things that may have saved me from becoming a full-blown crank before I reached the age of twenty-two; at some basic level I understood the absurdity of my vision, how wide the gap was between my grand ambitions and anything I was actually doing in my life. I was like a young Walter Mitty; a Don Quixote with no Sancho Panza.

This, too, can be found in my journal entries from that time, a pretty accurate chronicle of all my shortcomings. My preference for navel-gazing over action. A certain reserve, even shyness, traceable perhaps to my Hawaiian and Indonesian upbringing, but also the result of a deep self-consciousness. A sensitivity to rejection or looking stupid. Maybe even a fundamental laziness.

I took it upon myself to purge such softness with a regimen of self-improvement that I’ve never entirely shed. (Michelle and the girls point out that to this day I can’t get into a pool or the ocean without feeling compelled to swim laps. “Why don’t you just wade?” they’ll say with a snicker. “It’s fun. Here…we’ll show you how.”) I made lists. I started working out, going for runs around the Central Park Reservoir or along the East River and eating cans of tuna fish and hard-boiled eggs for fuel. I stripped myself of excess belongings—who needs more than five shirts?

What great contest was I preparing for? Whatever it was, I knew I wasn’t ready. That uncertainty, that self-doubt, kept me from settling too quickly on easy answers. I got into the habit of questioning my own assumptions, and this, I think, ultimately came in handy, not only because it prevented me from becoming insufferable, but because it inoculated me against the revolutionary formulas embraced by a lot of people on the left at the dawn of the Reagan era.

Certainly that was true when it came to questions of race. I experienced my fair share of racial slights and could see all too well the enduring legacy of slavery and Jim Crow anytime I walked through Harlem or parts of the Bronx. But, by dint of biography, I learned not to claim my own victimhood too readily and resisted the notion held by some of the Black folks I knew that white people were irredeemably racist.

The conviction that racism wasn’t inevitable may also explain my willingness to defend the American idea: what the country was, and what it could become.

My mother and grandparents had never been noisy in their patriotism. Reciting the Pledge of Allegiance in class, waving small flags on the Fourth of July—these were treated as pleasant rituals, not sacred duties (their attitudes toward Easter and Christmas were pretty much the same). Even Gramps’s service in World War II was downplayed; he told me more about eating K rations—“Terrible!”—than he ever told me about the glory of marching in Patton’s army.

And yet the pride in being American, the notion that America was the greatest country on earth—that was always a given. As a young man, I chafed against books that dismissed the notion of American exceptionalism; got into long, drawn-out arguments with friends who insisted the American hegemon was the root of oppression worldwide. I had lived overseas; I knew too much. That America fell perpetually short of its ideals, I readily conceded. The version of American history taught in schools, with slavery glossed over and the slaughter of Native Americans all but omitted—that, I did not defend. The blundering exercise of military power, the rapaciousness of multinationals—yeah, yeah, I got all that.

But the idea of America, the promise of America: this I clung to with a stubbornness that surprised even me. “We hold these truths to be self-evident, that all men are created equal”—that was my America. The America Tocqueville wrote about, the countryside of Whitman and Thoreau, with no person my inferior or my better; the America of pioneers heading west in search of a better life or immigrants landing on Ellis Island, propelled by a yearning for freedom.

It was the America of Thomas Edison and the Wright brothers, making dreams take flight, and Jackie Robinson stealing home. It was Chuck Berry and Bob Dylan, Billie Holiday at the Village Vanguard and Johnny Cash at Folsom State Prison—all those misfits who took the scraps that others overlooked or discarded and made beauty no one had seen before.

It was the America of Lincoln at Gettysburg, and Jane Addams toiling in a Chicago settlement home, and weary GIs at Normandy, and Dr. King on the National Mall summoning courage in others and in himself.

It was the Constitution and the Bill of Rights, crafted by flawed but brilliant thinkers who reasoned their way to a system at once sturdy and capable of change.

An America that could explain me.

“Dream on, Barack” is how those arguments with my college friends would usually end, as some smug bastard dropped a newspaper in front of me, its headlines trumpeting the U.S. invasion of Grenada or cuts in the school lunch program or some other disheartening news. “Sorry, but that’s your America.” —

SUCH WAS MY state when I graduated in 1983: big ideas and nowhere to go. There were no movements to join, no selfless leader to follow. The closest I could find to what I had in mind was something called “community organizing”—grassroots work that brought ordinary people together around issues of local concern. After bouncing around in a couple of ill-fitting jobs in New York, I heard about a position in Chicago, working with a group of churches that were trying to stabilize communities racked by steel plant closures. Nothing grand, but a place to start.

I’ve recorded elsewhere my organizing years in Chicago. Victories were small and transitory in the mostly Black working-class neighborhoods where I spent my time; my organization was a bit player in its attempts to address the changes that were sweeping not just Chicago but cities across the country—the decline of manufacturing, white flight, the rise of a discrete and disconnected underclass even as a new knowledge class began to fuel gentrification in the urban core.

But if my own impact on Chicago was small, the city changed the arc of my life.

For starters, it got me out of my own head. I had to listen to, and not just theorize about, what mattered to people. I had to ask strangers to join me and one another on real-life projects—fixing up a park, or removing asbestos from a housing project, or starting an after-school program. I experienced failure and learned to buck up so I could rally those who’d put their trust in me. I suffered rejections and insults often enough to stop fearing them.

In other words, I grew up—and got my sense of humor back.

I came to love the men and women I worked with: the single mom living on a ravaged block who somehow got all four children through college; the Irish priest who threw open the church doors every evening so that kids had an option other than gangs; the laid-off steelworker who went back to school to become a social worker. Their stories of hardship and their modest victories confirmed for me again and again the basic decency of people. Through them, I saw the transformation that took place when citizens held their leaders and institutions to account, even on something as small as putting in a stop sign on a busy corner or getting more police patrols. I noticed how people stood up a little straighter, saw themselves differently, when they learned that their voices mattered.

Through them, I resolved the lingering questions of my racial identity. For it turned out there was no single way to be Black; just trying to be a good man was enough.

Through them, I discovered a community of faith—that it was okay to doubt, to question, and still reach for something beyond the here and now.

And because I heard in church basements and on bungalow porches the very same values—honesty, and hard work, and empathy—that had been drilled into me by my mother and grandparents, I came to trust the common thread that existed between people.

I can’t help but wonder sometimes what would have happened if I had stayed with organizing, or at least some version of it. Like many local heroes I’ve met over the years, I might have managed to build up an institution that could reshape a neighborhood or a portion of the city. Anchored deep in a community, I might have steered money and imagination to change not the world but just that one place or that one set of kids, doing work that touched the lives of neighbors and friends in some measurable and useful way.

But I didn’t stay. I left for Harvard Law School. And here’s where the story gets murkier in my mind, with my motives open to interpretation.

I TOLD MYSELF THEN—and like to tell myself still—that I left organizing because I saw the work I was doing as too slow, too limited, not able to match the needs of the people I hoped to serve. A local job-training center couldn’t make up for thousands of steel jobs lost by a plant closing. An after-school program couldn’t compensate for chronically underfunded schools, or kids raised by their grandparents because both parents were doing time. On every issue, it seemed, we kept bumping up against somebody—a politician, a bureaucrat, some distant CEO—who had the power to make things better but didn’t. And when we did get concessions from them, it was most often too little, too late. The power to shape budgets and guide policy was what we needed, and that power lay elsewhere.

Moreover, I came to realize that just two years before I arrived, there had been a movement for change in Chicago, one that was both social and political—a deep swift current that I had failed to fully appreciate because it hadn’t conformed to my theories. It was the movement to elect Harold Washington as the city’s first Black mayor.

It seemed like it sprang out of nowhere, as grassroots a political campaign as anything modern politics had ever seen. A small band of Black activists and business leaders, tired of the chronic bias and inequities of America’s most segregated big city, decided to register a record number of voters, and then drafted a rotund congressman of prodigious talent but limited ambition to run for an office that appeared well out of reach.

Nobody thought it had a chance; even Harold was skeptical. The campaign operated hand to mouth, staffed largely by inexperienced volunteers. But then it happened—some form of spontaneous combustion. People who had never thought about politics, people who had never even voted, got swept up in the cause. Seniors and schoolchildren started sporting the campaign’s blue buttons. A collective unwillingness to keep putting up with a steady accumulation of unfairness and slights—all the bogus traffic stops and secondhand textbooks; all the times Black folks walked past a Park District field house on the North Side and noticed how much nicer it was than the one in their neighborhood; all the times they’d been passed over for promotions or denied bank loans—gathered like a cyclone and toppled city hall.

By the time I arrived in Chicago, Harold was halfway through his first term. The city council, once a rubber stamp for Old Man Daley, had divided into racial camps, a controlling majority of white aldermen blocking every reform that Harold proposed. He tried to wheedle and cut deals, but they wouldn’t budge. It was riveting television, tribal and raw, but it limited what Harold could deliver for those who’d elected him. It took a federal court redrawing a racially gerrymandered aldermanic map for Harold to finally get the majority and break the deadlock. And before he could realize many of the changes he’d promised, he was dead of a heart attack. A scion of the old order, Rich Daley, ultimately regained his father’s throne.

Far from the center of the action, I watched this drama unfold and tried to absorb its lessons. I saw how the tremendous energy of the movement couldn’t be sustained without structure, organization, and skills in governance. I saw how a political campaign based on racial redress, no matter how reasonable, generated fear and backlash and ultimately placed limits on progress. And in the rapid collapse of Harold’s coalition after his death, I saw the danger of relying on a single charismatic leader to bring about change.

And yet what a force he was for those five years. Despite the roadblocks, Chicago changed on his watch. City services, from tree trimming to snow removal to road repair, came to be spread more evenly across wards. New schools were built in poor neighborhoods. City jobs were no longer subject solely to patronage, and the business community at long last started paying attention to the lack of diversity in their ranks.

Above all, Harold gave people hope. The way Black Chicagoans talked about him in those years was reminiscent of how a certain generation of white progressives talked about Bobby Kennedy—it wasn’t so much what he did as how he made you feel. Like anything was possible. Like the world was yours to remake.

For me, this planted a seed. It made me think for the first time that I wanted to someday run for public office. (I wasn’t the only one thus inspired—it was shortly after Harold’s election that Jesse Jackson would announce he was running for president.) Wasn’t this where the energy of the civil rights movement had migrated—into electoral politics? John Lewis, Andrew Young, Julian Bond—hadn’t they run for office, deciding this was the arena where they could make the most difference? I knew there were pitfalls—the compromises, the constant money chase, the losing track of ideals, and the relentless pursuit of winning.

But maybe there was another way. Maybe you could generate the same energy, the same sense of purpose, not just within the Black community but across racial lines. Maybe with enough preparation, policy know-how, and management skills, you could avoid some of Harold’s mistakes. Maybe the principles of organizing could be marshaled not just to run a campaign but to govern—to encourage participation and active citizenship among those who’d been left out, and to teach them not just to trust their elected leaders, but to trust one another, and themselves.

That’s what I told myself. But it wasn’t the whole story. I was also struggling with narrower questions of my own ambitions. As much as I’d learned from organizing, I didn’t have much to show for it in terms of concrete accomplishments. Even my mother, the woman who’d always marched to a different drummer, worried about me.

“I don’t know, Bar,” she told me one Christmas. “You can spend a lifetime working outside institutions. But you might get more done trying to change those institutions from the inside.

“Plus, take it from me,” she said with a rueful laugh. “Being broke is overrated.”

And so it was that in the fall of 1988, I took my ambitions to a place where ambition hardly stood out. Valedictorians, student body presidents, Latin scholars, debate champions—the people I found at Harvard Law School were generally impressive young men and women who, unlike me, had grown up with the justifiable conviction that they were destined to lead lives of consequence. That I ended up doing well there I attribute mostly to the fact that I was a few years older than my classmates. Whereas many felt burdened by the workload, for me days spent in the library—or, better yet, on the couch of my off-campus apartment, a ball game on with the sound muted—felt like an absolute luxury after three years of organizing community meetings and knocking on doors in the cold.

There was also this: The study of law, it turned out, wasn’t so different from what I’d done during my years of solitary musing on civic questions. What principles should govern the relationship between the individual and society, and how far did our obligations to others extend? How much should the government regulate the market? How does social change happen, and how can rules ensure that everybody has a voice?

I couldn’t get enough of this stuff. I loved the back-and-forth, especially with the more conservative students, who despite our disagreements seemed to appreciate the fact that I took their arguments seriously. In classroom discussions, my hand kept shooting up, earning me some well-deserved eye rolls. I couldn’t help it; it was as if, after years of locking myself away with a strange obsession—like juggling, say, or sword swallowing—I now found myself in circus school.

Enthusiasm makes up for a host of deficiencies, I tell my daughters—and at least that was true for me at Harvard. In my second year, I was elected the first Black head of the Law Review, which generated a bit of national press. I signed a contract to write a book. Job offers arrived from around the country, and it was assumed that my path was now charted, just as it had been for my predecessors at the Law Review: I’d clerk for a Supreme Court justice, work for a top law firm or the Office of the United States Attorney, and when the time was right, I could, if I wanted to, try my hand at politics.

It was heady stuff. The only person who questioned this smooth path of ascent seemed to be me. It had come too quickly. The big salaries being dangled, the attention—it felt like a trap.

Luckily I had time to consider my next move. And anyway, the most important decision ahead would end up having nothing to do with law.

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