He had this really refreshing dream and I was like, “Barack, no, no, no. Not going to happen.”
—THE REVEREND JEREMIAH A. WRIGHT
Barack Obama arrived in Chicago in June 1985 at a tender twenty-three years of age, still wildly idealistic about the intrinsic goodness of mankind. But Obama’s first Chicago experience would open his youthful eyes to how cynical, complicated and unjust the world can be—especially when politics, race and power are as inextricably intertwined as they are in the largest middle-American city. But these Chicago years also educated Obama about more than the shortcomings of human beings. For a mixed-race young man, it was his first deep immersion into the African-American community that he had longed to both understand and belong to. The means by which he was immersed in this society—through community organizing—also made a lasting imprint on Obama, an impression that would greatly affect how he later conducted himself as a politician.
After he rolled into the City of Big Shoulders in a beat-up old Honda, Obama still kept a daily journal of his observations and emotions, still read philosophy and literature extensively and still led a rather isolated personal life. His daily existence so resembled the solitary life of a writer that some of his fellow community organizers wondered whether he had undertaken organizing simply to find grist for his version of the great American novel. They would not be too far off, for a few years later Obama would vividly recount his time in Chicago when writing Dreams, although the prose would be a loose form of nonfiction. According to Jerry Kellman, “One of the things Barack thought he might want to be is a writer. When he came to Chicago, he was still contemplating that. He wrote short stories. That’s a very different side from where he eventually went. He talked about how his father had made some wrong moves and wound up destitute, and he didn’t want that for himself.”
Obama was drawn to community organizing because it forced him directly into neighborhoods of poverty and despair. In New York, a former activist whose nonprofit had grown into a powerful entity reviewed Obama’s résumé and offered him a job that seemed to fit his well-educated skill set—organizing conferences and lobbying politicians on behalf of poor black communities. But Obama wanted to be closer to the real lives of the dispossessed and dispirited, and he turned down the offer. Community organizing in Chicago placed Obama in the midst of a unique American culture. Chicago’s South Side is filled with neighborhood upon neighborhood of African Americans, the largest single grouping of blacks anywhere in the nation. In the mid-1980s, the South Side ranged from communities of the stable middle class to neighborhoods of dire poverty. In the poor neighborhoods, violence, drugs and crime infected nearly every aspect of daily life. But even in some of the predominantly middle-class sections, a significant class dichotomy between middle and low income was present, creating tension between neighbors, between the haves and have-nots.
Kellman assigned Obama to the Roseland and West Pullman neighborhoods on the city’s Far South Side. Kellman was Obama’s tutor and sounding board through his many frustrations of organizing people who were financially poor, confused about authority and, in some cases, illiterate. Kellman cautioned Obama that his task would not be easy and that he should be prepared for utter failure, but that if he concentrated on a few specific problems, he could make a difference. “All I had to do was to teach him not to be idealistic and he did the rest,” Kellman said. “You can’t go out there and do any kind of significant political work or organizing and be idealistic. And he was idealistic, almost ridiculously so. You know, it is in his nature. He was a dreamer. But at the same time, you can’t perceive people through rose-colored glasses—right away, you have to get a sense of them.”
Roseland, once a Dutch farming community named for the bushes that thrived in its soil, reflected a schism in prosperity. The neighborhood is nearly all black and is adorned with street after street of well-manicured lawns and well-maintained houses. But it is also home to the occasional block of blight, poverty, unemployment and crime. That makes the lives of all its residents vastly more precarious than those of, say, the city’s whites on the Northwest Side. “For the middle class, it’s hard to maintain the high lofty goals you have for yourself when this abject poverty is all around you,” said Pat DeBonnett, executive director of a nonprofit group devoted to bringing business to several Far South Side neighborhoods. During the migration of southern blacks to Chicago from 1914 through the 1950s, Roseland suffered extreme disinvestment as nearly all its white inhabitants departed. White flight, in turn, translated into depressed property values, which translated into mortgage defaults, business failures, housing foreclosures, crime and unemployment. Then, in the 1980s, the decline of the South Side industrial base stung Roseland. By the mid-1980s, about one in six Roseland residents lived below the poverty line. The ubiquitous presence of the poor created an emotional paradox for middle-class blacks. Residents of moderate wealth were mindful that their neighbors lived in deprivation, a situation that instills a sense of compassion for those less fortunate. But middle-class blacks also harbored some resentment toward their poor neighbors because they dragged down the community’s overall standard of living. “It creates a real division in a community—and I’d even say a sense of division within the race,” DeBonnett said.
Into this uncomfortable, complicated stew dropped Obama. Kellman had hired him to launch the Developing Communities Project, an ecumenically funded group whose mission still today is to empower the poor and disenfranchised through grassroots organization. The group is based in the community organizing tradition of Saul Alinsky. Alinsky’s activism in the first half of the twentieth century ran parallel with the labor movement, although he expanded the theory of organizing people to include grievances other than employment. Born in 1909, Alinsky grew up in Chicago’s gritty Back of the Yards neighborhood during the Great Depression. He made his first political efforts in his home community of blue-collar European immigrants, organizing meatpackers to agitate for better working conditions. He believed in public confrontation in the form of sit-ins and boycotts, but his success stemmed mainly from instilling people with the belief that they had the power to redefine their own lives, through both activism and personal behavior. In his manifesto Rules for Radicals, Alinsky wrote, “When we talk about a person’s lifting himself by his own bootstraps, we are talking about power. Power must be understood for what it is, for the part it plays in every area of our life, if we are to understand it and thereby grasp the essentials of relationships and functions between groups and organizations, particularly in a pluralistic society. To know power and not fear it is essential to its constructive use and control.” Alinsky taught organizers to work behind the scenes, listening to residents for hours upon hours to decipher what their community needed and what it could realistically achieve.
Alinsky’s life mission and his methodologies are both central to Obama’s modern political message. As noted before, a recurring passage in many of Obama’s speeches is his mission of “giving voice to the voiceless and power to the powerless.” But Obama also speaks frequently about self-reliance as the most effective means of ultimately pulling oneself out of financial and social distress. Alinsky himself was politically active, traveling the country and attempting to politicize the masses. In the process, he established an institute that trained, among others, Cesar Chavez, founder of the United Farm Workers union. Alinsky’s work also influenced the civil rights movement and anti–Vietnam War protestors. Obama wrote that he was drawn to Alinsky’s form of direct action. “Once I found an issue people cared about, I could take them into action. With enough actions, I could start to build power. Issues, actions, power, self-interest. I liked these concepts. They bespoke a certain hardheadedness, a worldly lack of sentiment; politics, not religion.”
One of Obama’s initial discoveries about Chicago’s broad swath of South Side African-American communities was the power and influence of the church in these neighborhoods. Whether it was the Catholic Church, African Methodist, Baptist or something else, the larger churches and their pastors exercised great influence over the local politics. And this was the first hard lesson that Obama learned about these institutions: Most of these ministers operated independently of the others, to the degree that they competed for congregants—and competed for power. Obama had idealistic notions of uniting these various conflicting personas and personal agendas into a coherent whole, to work on behalf of the entire area. But it did not take long for him to learn just how discouraging that mission would be in reality. “It wasn’t until I came to Chicago and started organizing that all this stuff that was in my head sort of was tested against the reality,” Obama said. “And in some cases, it didn’t always work out. That’s why I say that the best education I ever received was as an organizer because it reminded me that you can look at a map, but that’s not the actual territory.”
ONE OF THE MOST INFLUENTIAL OF THESE SOUTH SIDE PASTORS was Jeremiah A. Wright of the Trinity United Church of Christ. Wright tried to explain to Obama that the terrain on the map was treacherous. In fact, Wright counseled the young Obama that his dream of unifying the Chicago pastors was impossible:
The first day we met, I said, “Do you remember the story about Joseph in the Old Testament, where he had these dreams and he shared them with his brothers? Then one day, Joseph was coming across the field toward his brothers and they said, ‘Behold, the Dreamer.’” I told him, “That’s what I feel like when I listen to you, Barack. You are a dreamer.” He came up with this dream of organizing the churches of Chicago like you would organize the churches in New York or on the East Coast. His vision and view was to implement significant change and meaningful change that benefited people, real people. Not politics, not self-aggrandizement, not worrying about which politicians would look good. But how can we bring about change in our communities that the people want and need? I said to him, “Oh, that sounds good, Barack, real good. But you don’t know Chicago, do you?” [Wright then broke into a hearty laugh.] Barack said to me, “You are a minister. Why are you sounding so skeptical?” . . . And I said, “Man, these preachers in Chicago. You are not going to organize us. That’s not going to happen.” He had this really refreshing dream and I was like, “Barack, no, no, no. Not going to happen.”
Wright’s pessimism was born in a cold reality, a lesson Obama would soon take to heart. In Dreams, he recounted a community police meeting that he organized in which one minister derided him for being a naive pawn in the hands of Chicago’s whites—lakefront Jewish liberals and the Roman Catholic Church. Indeed, individuals from both of those groups were benefactors of Kellman’s Developing Communities Project. The meeting “was a disaster,” Obama said. At this juncture in his life, Obama’s religious beliefs were similar to his mother’s—a secular humanist who was largely agnostic. In Dreams, Obama described how religion was being used in Chicago’s churches, and he questioned the true power of religious faith and religious institutions to make positive change: “For there were many churches, many faiths. There were times, perhaps when those faiths seem to converge—the crowd in front of the Lincoln Memorial, the Freedom Riders at the lunch counter. But such moments were partial, fragmentary. With our eyes closed, we uttered the same words, but in our hearts we prayed to our own masters; we each remained locked in our own memories; we all clung to our own foolish magic.”
A main tenet of the Alinsky organizing philosophy was attention to listening—to pull together the masses for a common cause, the organizer must hear and understand the limitations, the fears and the experiences of the people being assembled. Working out of a small office in a church, Obama was assigned to conduct twenty to thirty interviews each week. Residents initially were wary of this overly serious young man from out of town, but Obama slowly gained their trust. “I’m here to do serious work,” he told them. Over time, residents began calling him “Baby Face” for his youthful looks. Obama was known for his detailed and calculated planning, a trait he would carry into politics. He did not like to be surprised in a meeting and he especially loathed being unprepared. Kellman’s first major project for Obama was assisting the people of a housing project called Altgeld Gardens. Altgeld’s sprawling apartment complex was inhabited by two thousand residents, nearly all of them black. Situated just outside Roseland, it was built in the 1940s to house manufacturing laborers for surrounding factories. The complex sits in relative physical isolation amid a huge garbage dump, a noxious-smelling sewage plant, a paint factory and the heavily polluted Calumet River. Altgeld is in a constant state of disrepair, and circumstances have improved only slightly a generation later. Obama’s group was one of two working in Altgeld to organize parents and others, with the mission of pushing the Chicago Housing Authority to repair toilets, windows and the heating system. To some extent, Obama’s efforts were successful. He organized residents to successfully lobby city hall to open a job bank, learning along the way that blacks still viewed the labor movement with suspicion. Chicago’s trade unions historically had excluded blacks from their ranks, especially as manufacturing jobs dried up.
Of Obama’s pursuits in Altgeld, a campaign to remove asbestos drew the most public attention, even if Obama himself garnered practically no publicity. He helped organize two meetings in downtown Chicago. One resulted in the housing authority testing Altgeld for asbestos and persuading an alderman, Bobby Rush, to hold city council hearings on the matter. A second meeting saw a group of several hundred travel downtown for a raucous visit with city officials. That confrontation prompted the housing authority to hire workers to seal off the asbestos. “He was our motivator,” resident Callie Smith said of Obama. Kellman suggests that Obama downplayed his own significance because, as an organizer, he wanted to remain behind the scenes and allow the residents to be the public faces of discontent. For instance, Kellman said it was actually Obama who noticed a newspaper ad for asbestos removal services in the main administration building at Altgeld, even though in his book Obama credits an activist he called “Sadie.” The ad prompted residents to question whether asbestos was in other parts of the complex too.
When writing his first memoir, Obama made Kellman one of his main Chicago characters, bestowing on him the pseudonym “Marty Kaufman.” “Jerry Kellman is whip smart,” Obama told me. “One of the smartest men I’ve ever met.” In Dreams, Obama described Kellman (or Kaufman) as a bespectacled, ordinary-looking white man in his middle thirties who typically needed a shave and seemed a bit too sure of himself. When I met Kellman in March 2006, he seemed much the same man, only now in his mid-fifties, a bit more put together but still quite certain of his own words. A New York Jew who converted to Catholicism, Kellman described himself as a “recovering organizer,” giving me the impression that he did not view his organizing years with joy. He still worked in a modest-paying job that assisted the poor and disaffected, serving as director of a Roman Catholic social services project in an inner-ring suburb just north of Chicago.
Physically, it was difficult to recall specifics of his face only hours after our interview. But the substance of the interview was etched in my mind for days. Kellman’s voice would occasionally drop into such a low pitch that I was drawn to it, not only because I had to strain to hear it, but because it seemed as if he was earnestly imparting a piece of wisdom that he deeply believed—and deeply wanted his listener to believe. His insight into Obama was extraordinarily intimate and accurate, not surprisingly since the two had been daily confidants for almost three years. They talked about everything from community organizing to Obama’s vision for his future. Kellman’s main mission seemed to be to keep Obama from burning out. He urged him to pursue a more active social life to take a break from the depressing moments of organizing. Obama, who initially was spending most of his weekends reading books, eventually heeded this advice. He started dating and had a live-in girlfriend for a while. But when that relationship ended, it was painful for Obama, who conceded that his own lack of maturity partly contributed to its demise.
Like Obama’s grandmother, Kellman described Obama as a man on a mission to serve society. Obama told Kellman that he had been extremely fortunate in his own life, and so he felt a passion to contribute to the betterment of others’ lives, especially by pushing for economic and social progress in the black community. “Barack wanted to serve; he wanted to lead,” Kellman said. “And he was ambitious, but never just for ambition’s sake. It was always mixed in with a sense of service. He is motivated by [a desire for] significant structural change for people he cares about. And he found himself in the African-American community, historically, intellectually and, finally, geographically.”
The two men fell out of touch after Obama left Chicago for Harvard Law School, and thereafter Obama’s life grew busier and Kellman’s grew somewhat erratic. Kellman had not had an extended conversation with Obama since his rise to celebrity status, but in following his public career, he said, it seemed clear to him that the core of Obama’s character had remained essentially intact. He felt so devoted to Obama’s political cause, in fact, that he contributed fifteen hundred dollars to his Senate campaign. (“That’s not much, but it is a great amount for me, someone paid from the Catholic Church,” he said sheepishly. Not long after our interview, Kellman called Obama and the two men had an extended conversation.)
Before sending Obama off to Chicago’s projects, Kellman urged him to read Parting the Waters, the first of author Taylor Branch’s rich and thorough trilogy on the civil rights movement of the 1950s and ’60s. After finishing the book, Obama confessed to Kellman, “This is my story.” It would be yet another indication to Kellman of the seriousness with which Obama took both himself and his public work. But mostly it would be a sign that this man who had suffered such profound racial confusion was finally finding comfort as an American black man. Obama’s physical features, after all, give him this appearance. He has joked that cab drivers who passed him by on the streets of New York failed to see his maternal white relatives. Nor have most blacks looked at him and questioned his identity. “I think there are a lot of black and white intellectuals who like to use me as a Rorschach test for their own confusion about race,” Obama said. “And the truth of the matter is, you know, when I’m walking down the South Side of Chicago and visiting my barber shop and playing basketball in some of these neighborhoods, those aren’t questions I get asked.”
Kellman met with Obama on nearly a daily basis and observed as Obama grew more comfortable weaving in and out of the black community in those organizing years. After seeing how Obama’s political career unfolded, Kellman made a bold proclamation: Despite chatter in some quarters of the black community that Obama hadn’t lived the typical African-American experience, Kellman predicted that he would be the most likely heir to Martin Luther King’s legacy as both the chief advocate and the moral voice of black Americans. He said Obama saw this role for himself years ago, even if he is reluctant to admit it publicly today for fear of sounding immodest and perhaps distancing himself from his non-black constituents. Kellman also predicted that Obama would assume this mantle with thoughtfulness and a full understanding of its gravity.
“If you look at the King analogy and you look at Barack,” Kellman said, “Barack has become the expectation of his people, and in that sense he is similar to King. As I know Barack, he will carry that as a weight, but he will carry that burden with great seriousness. And obviously, that can cause someone to kind of lose perspective. You can get overly inflated. But it is also cause for some sobering loss of your own importance at the same time. I think he knows that if he wants to go where he wants to go in politics, he has to speak for more than the black community. But I think the rest of his life, he will take on that burden of being that person who changes the situation for African Americans.”
A SECOND MAN PLAYED A VITAL ROLE IN OBAMA’S CHICAGO experience—Reverend Wright. Obama noted the influential role that the church played in the lives of the African Americans he was organizing. “So I figured I better attend some services myself and see what it was all about,” he said. It was Wright’s church and his charismatic preaching that most closely spoke to Obama’s budding spiritual nature. In seeking a permanent American identity, Obama discovered that, in a religious land, his agnosticism relegated him to a place of isolation. “I came to realize that without a particular commitment to a particular community of faith,” he wrote in his book The Audacity of Hope, “I would be consigned at some level to always remain apart, free in the way that my mother was free, but also alone in the same ways that she was ultimately alone.”
Wright was among the most liberal of African-American preachers—he could be all fire and no brimstone. When Obama knocked on Trinity’s door, Wright was in his mid-forties and in the midst of growing his Trinity congregation to its present membership of nearly eight thousand. Burly and light-skinned, Wright is the son of a Baptist minister in Philadelphia. His intellectual sermons sometimes more resemble left-wing political rants than religious preaching. Startling for a preacher, he can be both profane and provocative. Despite advancing a multicultural agenda, like Obama, Wright’s church is rooted in Afrocentrism. Wright himself often dons colorful African dashikis and is not shy about laying historical and modern-day blame on whites for much of the social and economic woes in the African-American community. His sermons frequently denounce Republican politics, and he has called people who voted for George W. Bush “stupid.” Trinity United is considered among some Chicago blacks to be the church of elites, attracting celebrities like the rapper Common and TV talk mogul Oprah Winfrey to its congregation.
In some ways, Obama and Wright seem a mismatch because of their distinctively different styles. But in other ways, they seem like a perfect fit—an attraction of opposites. In contrast to Obama’s cautious style, Wright is bombastic, rebellious and, in his own estimation, unafraid to speak truth to power. Wright earned bachelor’s and master’s degrees in sacred music from Howard University and initially pursued a Ph.D. at the University of Chicago Divinity School before interrupting his studies to minister full-time. His intellectualism and black militancy put him at odds with some Baptist ministers around Chicago, with whom he often sparred publicly, and he finally accepted a position at Trinity. The church’s motto was “Unashamedly black and unapologetically Christian.” Wright unquestionably took that motto to heart.
Wright remains a maverick among Chicago’s vast assortment of black preachers. He will question Scripture when he feels it forsakes common sense; he is an ardent foe of mandatory school prayer; and he is a staunch advocate for homosexual rights, which is almost unheard-of among African-American ministers. Gay and lesbian couples, with hands clasped, can be spotted in Trinity’s pews each Sunday. Even if some blacks consider Wright’s church serving only the bourgeois set, his ministry attracts a broad cross section of Chicago’s black community. Obama first noticed the church because Wright had placed a “Free Africa” sign out front to protest continuing apartheid. The liberal, Columbia-educated Obama was attracted to Wright’s cerebral and inclusive nature, as opposed to the more socially conservative and less educated ministers around Chicago. Wright developed into a counselor and mentor to Obama as Obama sought to understand the power of Christianity in the lives of black Americans, and as he grappled with the complex vagaries of Chicago’s black political scene. “Trying to hold a conversation with a guy like Barack, and him trying to hold a conversation with some ministers, it’s like you are dating someone and she wants to talk to you about Rosie and what she saw on Oprah, and that’s it,” Wright explained. “But here I was, able to stay with him lockstep as we moved from topic to topic. . . . He felt comfortable asking me questions that were postmodern, post-Enlightenment and that college-educated and graduate school–trained people wrestle with when it comes to the faith. We talked about race and politics. I was not threatened by those questions.”
Wright also played an assisting role in another part of Obama’s evolution—from a questioner of religion to a practicing Christian. Along his Senate campaign trail, Obama would never fail to carry his Christian Bible. He would place it right beside him, in the small compartment in the passenger side door of the SUV, so he could refer to it often. When I first questioned Obama about his religious faith and ever-present Bible in October 2004, he seemed just a bit hesitant to answer. He was also uncharacteristically short in his responses. Obama, without fail, would mention his church and his Christian faith when he was campaigning in black churches and more socially conservative downstate Illinois communities. But in speaking to a reporter, it seemed that he had something to say about religion and politics, although he had yet to turn that inclination into a coherent message. He told me that he referred to his Bible a “couple times a week.” “It’s a great book and contains a lot of wisdom,” he said simply. When I pried further, he said he was drawn to Christianity because its main tenet of altruism and selflessness coincided with his own philosophies. “Working with churches and with people of faith, I think, made me recognize that many of the impulses that I had carried with me and were propelling me forward were the same impulses that express themselves through the church,” he said.
But more than that, Trinity’s less doctrinal approach to the Bible intrigued and attracted Obama. “Faith to him is how he sees the human condition,” Wright said. “Faith to him is not . . . litmus test, mouth-spouting, quoting Scripture. It’s what you do with your life, how you live your life. That’s far more important than beating someone over the head with Scripture that says women shouldn’t wear pants or if you drink, you’re going to hell. That’s just not who Barack is.”
Overall, Obama’s first Chicago experience proved powerful in his later development as a politician. His Christianity would be well received among blacks and some rural whites. Community organizing taught him that idealism must be coupled with pragmatism and hard realism. This would help him most prominently in his legislative work, when he realized that compromise was often necessary to move a bill forward. Organizing also turned this once self-absorbed teenager and college student into an attentive listener to other people’s concerns, a trait that enabled him to perceive the world through other people’s eyes and then communicate those concerns to voters.
Obama never got very far in his effort to organize Chicago’s pastors, but a magazine essay he wrote upon returning to Chicago a couple of years later showed that he had not lost hope for that dream. In the 1990 article, Obama called the African-American church “a slumbering giant in the political and economic landscape of cities like Chicago.” He continued: “Over the past few years, however, more and more young and forward-thinking pastors have begun to look at community organizations . . . as a powerful tool for living the social gospel, one which can educate and empower entire congregations and not just serve as a platform for a few prophetic leaders. Should a mere 50 prominent black churches, out of the thousands that exist in cities like Chicago, decide to collaborate with a trained organizing staff, enormous positive changes could be wrought in the education, housing, employment and spirit of inner-city black communities, changes that would send powerful ripples throughout the city.”
After some losses, some victories and new spirituality, Obama summed up his experience working for the Developing Communities Project by strongly endorsing community organizing as an effective means of advancing American society toward the ideal of equity and justice for all:
“In helping a group of housewives sit across the negotiating table with the mayor of America’s third largest city and hold their own, or a retired steelworker stand before a TV camera and give voice to the dreams he has for his grandchild’s future, one discovers the most significant and satisfying contribution organizing can make.
In return, organizing teaches as nothing else does the beauty and strength of everyday people. Through the songs of the church and the talk on the stoops, through the hundreds of individual stories of coming up from the South and finding any job that would pay, of raising families on threadbare budgets, of losing some children to drugs and watching others earn degrees and land jobs their parents could never aspire to—it is through these stories and songs of dashed hopes and powers of endurance, of ugliness and strife, subtlety and laughter, that organizers can shape a sense of community not only for others, but for themselves.