You are using an outdated browser.
Please upgrade your browser
and improve your visit to our site.
Skip Navigation

The Agitator

Barack Obama’s unlikely political education.

In 1985, Barack Obama traveled halfway across the country to take a job that he didn’t fully understand. But, while he knew little about his new vocation—community organizer—it still had a romantic ring, at least to his 24-year-old ears. With his old classmates from Columbia, he had talked frequently about political change. Now, he was moving to Chicago to put that talk into action. His 1995 memoir, Dreams from My Father, recounts his idealistic effusions: “Change won’t come from the top, I would say. Change will come from a mobilized grass roots. That’s what I’ll do. I’ll organize black folks. At the grass roots. For change.”

His excitement wasn’t rooted merely in youthful enthusiasm but also in the psychology of a vagabond. By 1985, Obama had already lived in Hawaii, where he was born and raised by his white mother and grandparents; Indonesia, where he lived briefly as a child; Los Angeles, where he started college; and New York, where he finished it. After these itinerant years, he would finally be able to insinuate himself into a community—and not just any community, but, as he later put it, “the capital of the African American community in the country.” Every strain of black political thought seemed to converge in Chicago in the 1980s. It was the intellectual center of black nationalism, the base both for Jesse Jackson’s presidential campaigns and for Louis Farrakhan’s Nation of Islam. Moreover, on the eve of Obama’s arrival, Harold Washington had overthrown Richard J. Daley’s white ethnic machine to become the city’s first black mayor. It was, in short, an ideal place for an identity-starved Kenyan Kansan to immerse himself in a more typical black American experience.

Not long after Obama arrived, he sat down for a cup of coffee in Hyde Park with a fellow organizer named Mike Kruglik. Obama’s work focused on helping poor blacks on Chicago’s South Side fight the city for things like job banks and asbestos removal. His teachers were schooled in a style of organizing devised by Saul Alinsky, the radical University of Chicago-trained social scientist. At the heart of the Alinsky method is the concept of “agitation”— making someone angry enough about the rotten state of his life that he agrees to take action to change it; or, as Alinsky himself described the job, to “rub raw the sores of discontent.”

On this particular evening, Kruglik was debriefing Obama about his work when a panhandler approached. Instead of ignoring the man, Obama confronted him. “Now, young man, is that really what you want to be about?” Obama demanded. “I mean, come on, don’t you want to be better than that? Let’s get yourself together.”

Kruglik remembers this episode as an example of why, in ten years of training organizers, Obama was the best student he ever had. He was a natural, the undisputed master of agitation, who could engage a room full of recruiting targets in a rapid-fire Socratic dialogue, nudging them to admit that they were not living up to their own standards. As with the panhandler, he could be aggressive and confrontational. With probing, sometimes personal questions, he would pinpoint the source of pain in their lives, tearing down their egos just enough before dangling a carrot of hope that they could make things better.

More than 20 years later, Obama presents himself as a post-partisan consensus builder, not a rabble-rouser, and certainly not a disciple of Alinsky, who disdained electoral politics and titled his organizing manifesto Rules for Radicals. On the stump, Obama makes a pitch for “common-sense, practical, non-ideological solutions.” And, although he’s anchored to a center-left worldview, he gives the impression of being above the ideological fray—a fresh face who is a generation removed from the polarizing turmoil of the 1960s. The mirror he holds up is invariably flattering—reflecting back a tolerant, forward-looking electorate ready to unite around his consensus-minded brand of politics. Indeed, if there has been a knock on Obama’s campaign in these early days, it’s that it may be a bit too idealistic for the realities of a presidential race. With his lofty rhetoric and careful positioning as above politics, Obama in some ways recalls Bill Bradley, another candidate of moral purity—and one whose unwillingness to engage in the rough-and-tumble of modern politics ultimately proved his undoing.

Yet Obama connects his past as a Chicago organizer to his presidential bid with surprising ease. Last month, during his first visit to South Carolina since his campaign announcement, we discussed his community-organizing days. He sat at the head of along table inside a dimly lit hotel conference room in Columbia and ate a chocolate energy bar. When I began to suggest links between his organizing work then and his current campaign, he interrupted:”I think there is. I don’t think you need to strain for it.” He was at home talking Alinskian jargon about “agitation,” which he defined as “challenging people to scrape away habit,” and he fondly recalled organizing workshops where he learned the concept of “being predisposed to other people’s power.”

Publicly, as well, Obama has made his organizing days central to his political identity. When he announced his candidacy for president last month, he said the “best education” he ever had was not his undergraduate years at Occidental and Columbia or even his time at Harvard Law School, but rather the four years he spent in the mid-’80s learning the science of community organizing in Chicago. The night after Obama’s announcement speech, he made a similar point on “60 Minutes” as he led Steve Kroft around the old neighborhood.

Obama’s self-conception as an organizer isn’t just a campaign gimmick. Organizing remained central to Obama long after his stint on the South Side. In the 13 years between Obama’s return to Chicago from law school and his Senate campaign, he was deeply involved with the city’s constellation of community- organizing groups. He wrote about the subject. He attended organizing seminars. He served on the boards of foundations that support community organizing. He taught Alinsky’s concepts and methods in workshops. When he first ran for office in 1996, he pledged to bring the spirit of community organizing to his job in the state Senate. And, after he was elected to the U.S. Senate, his wife, Michelle, told a reporter, “Barack is not a politician first and foremost. He’s a community activist exploring the viability of politics to make change.” Recalling her remark in 2005, Obama wrote, “I take that observation as a compliment.”

By defining himself as a “community organizer” above all else, Obama is linking himself to America’s radical democratic tradition and presenting himself as an heir to a particular political style and methodology that, at least superficially, contrasts sharply with the candidate Obama has become. Community organizers see themselves as disciples of Thomas Paine and the colonists who dumped tea in Boston Harbor. Historically, they have revered the tactics of the labor militants of the 1930s, and they became famous in the ‘60s for the political theater championed by Alinsky, illustrated most memorably by his threat of a “fart-in” at a Rochester, New York, opera house to bring attention to the Kodak company’s refusal to hire blacks.

Needless to say, this doesn’t sound much like the placid politician who wrote The Audacity of Hope. And it raises questions about Obama’s authentic political identity that require traveling back to the years when community organizing gave him the best education of his life.

A year after graduating from Columbia, Obama spotted an intriguing help-wanted ad in The New York Times. The Calumet Community Religious Conference (CCRC), a group that aimed to convert the black churches of Chicago’s South Side into agents of social change, was looking for a community organizer to run the group’s inner-city arm, the Developing Communities Project (DCP). Obama soon arranged to meet in New York with the organizer heading up the job search.

Obama had spent the previous year on a fruitless quest. He worked briefly for a Ralph Nader outfit in Harlem teaching college kids about recycling and then on a losing assemblyman’s race in Brooklyn. But he longed for an experience that connected him to the civil rights era. “In the sit-ins, the marches, the jailhouse songs,” he wrote in Dreams, “I saw the African-American community becoming more than just the place where you’d been born or the house where you’d been raised. Through organizing, through shared sacrifice, membership had been earned.” Obama wanted to join the club.

“What really inspired me,” Obama told me during one of several conversations about his work as an organizer, “was the civil rights movement. And if you asked me who my role model was at that time, it would probably be Bob Moses, the famous SNCC [Student Nonviolent Coordinating Committee] organizer. ... Those were the folks I was really inspired by—the John Lewises, the Bob Moseses, the Fannie Lou Hamers, the Ella Bakers.”

Instead, he got Gerald Kellman, a Jewish organizer in a rumpled, tea-stained shirt. While Obama was in search of an authentic African American experience, Kellman was simply in search of an authentic African American. His organization worked in black neighborhoods decimated by the shuttering of economic behemoths like U.S. Steel, agitating the unemployed to demand jobs and safer streets. But, for all the anger and poverty in these places, Kellman and his comrades couldn’t break through. Because he and his fellow organizers, Mike Kruglik and Gregory Galluzzo, were white (and two of the three were Jewish), the black pastors viewed them with suspicion and, in some cases, outright disdain. Kellman, who had paid what he considered a small fortune for the Times ad, desperately needed a young black man to give the group credibility.

The job with the DCP allowed Obama entree into the poor black neighborhoods with which he was so eager to connect. But serving as the black representative for a trio of white organizers wasn’t exactly the community-organizing fantasy he had in mind. Rather, as Obama says today, “This was the closest I could find. “ Kellman, Kruglik, and Galluzzo weren’t schooled in civil rights-era organizing, but in the teachings of Alinsky, who distrusted movement politics and even Martin Luther King Jr. But, although Obama didn’t quite find himself reliving the civil rights era, he soon found himself succumbing to the appeal of Alinsky’s organizing methodology.

In Dreams, Obama spent some 150 pages on his four years in Chicago working as an organizer, but there’s little discussion of the theory that undergirded his work and informed that of his teachers. Alinsky is the missing layer of his account.

Born in 1909 to Russian-Jewish immigrants, Alinsky had prowled the same neighborhoods that Obama now worked and internalized many of the same lessons. As a University of Chicago criminology graduate student, he ingratiated himself with Al Capone’s mobsters to learn all he could about the dynamics of the city’s underworld, an experience that helped foster a lifelong appreciation for seeing the world as it actually exists, rather than through the academic’s idealized prism. Charming and self-absorbed, Alinsky would entertain friends with stories—some true, many embellished—from his mob days for decades afterward. He was profane, outspoken, and narcissistic, always the center of attention despite his tweedy, academic look and thick, horn-rimmed glasses.

Alinsky was deeply influenced by the great social science insight of his times, one developed by his professors at Chicago: that the pathologies of the urban poor were not hereditary but environmental. This idea, that people could change their lives by changing their surroundings, led him to take an obscure social science phrase—”the community organization”—and turn it into, in the words of Alinsky biographer Sanford Horwitt, “something controversial, important, even romantic.” His starting point was a near-fascination with John L. Lewis, the great labor leader and founder of the CIO. What if, Alinsky wondered, the same hardheaded tactics used by unions could be applied to the relationship between citizens and public officials?

To test his theory, Alinsky left the world of academia in the 1930s and set up shop in Chicago’s meatpacking neighborhood, the “Back of the Yards”—the same wretched, multiethnic enclave that Upton Sinclair had chronicled three decades earlier in The Jungle. He created the Back of the Yards Neighborhood Council, which won a succession of victories against businesses and decreased crime, while increasing cooperation between rival ethnic groups. The results were impressive enough that they were celebrated far beyond Chicago in newspaper stories with headlines like, “they called him a ‘red,’ but young sociologist did the job.”

Alinsky had been dead for more than a decade when Obama arrived in Chicago, but his legacy was still very much alive. Kruglik, Kellman, and Galluzzo had all studied his teachings through the Industrial Areas Foundation (IAF), the organizing school Alinsky founded. By the ‘80s, not even the IAF strictly adhered to every principle that Alinsky taught. But at least one of Obama’s teachers considered himself a true believer: “I regard myself as St. Paul who never met Jesus,” Galluzzo told me of Alinsky, who died shortly after Galluzzo moved to Chicago on a pilgrimage to meet him in 1972. “I’m his best disciple.” Alinsky has attracted other, more famous admirers, including Hillary Clinton, who wrote an undergraduate thesis about him, a favorite bit of trivia for right-wingers.

But, while Alinsky is often viewed as an ideological figure—toward the end of his life, New Left radicals tried to claim him as one of their own—to place Alinsky within a taxonomy of left-wing politics is to miss the point. His legacy is less ideological than methodological. Alinsky’s contribution to community organizing was to create a set of rules, a clear-eyed and systemic approach that ordinary citizens can use to gain public power. The first and most fundamental lesson Obama learned was to reassess his understanding of power. Horwitt says that, when Alinsky would ask new students why they wanted to organize, they would invariably respond with selfless bromides about wanting to help others. Alinsky would then scream back at them that there was a one-word answer: “You want to organize for power!”

Galluzzo shared with me the manual he uses to train new organizers, which is little different from the version he used to train Obama in the ‘80s. It is filled with workshops and chapter headings on understanding power: “power analysis,” “elements of a power organization,” “the path to power.” Galluzzo told me that many new trainees have an aversion to Alinsky’s gritty approach because they come to organizing as idealists rather than realists. But Galluzzo’s manual instructs them to get over these hang-ups. “We are not virtuous by not wanting power,” it says. “We are really cowards for not wanting power,” because “power is good” and “powerlessness is evil.”

The other fundamental lesson Obama was taught is Alinsky’s maxim that self-interest is the only principle around which to organize people. (Galluzzo’s manual goes so far as to advise trainees in block letters: “get rid of do-gooders in your church and your organization.”) Obama was a fan of Alinsky’s realistic streak. “The key to creating successful organizations was making sure people’s self-interest was met,” he told me, “and not just basing it on pie-in-the-sky idealism. So there were some basic principles that remained powerful then, and in fact I still believe in.”

Chicago pastors still remember Obama making the rounds of local churches and conducting interviews—in organizing lingo, “one-on-ones”—where he would probe for self-interest. The Reverend Alvin Love, the Baptist minister of a modest brick church amid the clapboard bungalows of the South Side, was one of Obama’s first one-on-ones. During a recent visit to his church, Love told me, “I remember he said this to me: ‘There ought to be some way for us to help you meet your self-interest while at the same time meeting the real interests and the needs of the community.’”

Obama so mastered the workshops on power that he later taught them himself. On his campaign website, one can find a photo of Obama ina classroom teaching students Alinskian methods. He stands in front of a blackboard on which he has written, “Power Analysis” and “Relationships Built on Self Interest,” an idea illustrated by a diagram of the flow of money from corporations to the mayor.

But, although he was a first-class student of Alinsky’s method, Obama also saw its limits. It appealed to his head but not his heart. For instance, Alinsky relished baiting politicians or low-level bureaucrats into public meetings where they would be humiliated. Obama found these “accountability sessions” unsettling, even cruel. “Oftentimes, these elected officials didn’t have that much more power than the people they represented,” he told me.

At one meeting, where residents of an asbestos-laden housing project confronted their property manager about whether their homes had been tested, Obama suddenly had the urge to warn his target. “I wanted to somehow let Mr. Anderson know that I understood his dilemma,” Obama wrote in Dreams, with the kind of empathy that is the hallmark of his autobiography. He was sometimes more interested in connecting with folks on the South Side than organizing them. He studied the characters he encountered so closely that Kruglik says Obama turned his field reports into short stories about the hopes and struggles of the local pastors and congregants with whom he was trying to commune.

Where some of Alinsky’s disciples speak of his work with religious fervor, Obama maintained some detachment during these years. In his memoir, he gently mocked Marty Kauffman, the character based on Kellman (and a touch of Kruglik), who is a little too clinical in his approach and never puts down any roots in the community. “[I]t occurred to me that he’d made no particular attachments to people or place during his three years in the area, that whatever human warmth or connection he might require came from elsewhere,” he wrote. Obama was determined not to end up like that. He needed something more than organizing theory to make the South Side his home.

As it was, he ran into the same roadblock as his trainers had. “Obama,” Galluzzo told me, “was constantly being harassed by people saying, ‘Oh, you work for that white person.’” On one occasion, he eagerly tried to make his pitch about joining DCP to a Reverend Smalls. Smalls wasn’t interested. “I think I remember some white man coming around talking about some developing something or other,” he told Obama. “Funny-looking guy. Jewish name.” His hostility only grew when Obama explained that Catholic priests were also involved. “Listen ... what’s your name again? Obamba?” Smalls asked without waiting for an answer. “Listen, Obamba, you may mean well. I’m sure you do. But the last thing we need is to join upwith a bunch of white money and Catholic churches and Jewish organizers to solve our problems.” Obama left the meeting crestfallen.

On a Sunday morning two weeks before he launches his presidential campaign, Obama is at Trinity United Church of Christ on the South Side, gently swaying from side to side under a giant iron cross. From the outside, the church looks more like a fortress than a house of worship, with high white washed brick walls topped with security cameras. Inside, Trinity is the sort of African American community that the young Obama longed to connect with when he first came to Chicago. The church’s motto is “unashamedly black and unapologetically Christian,” and sunlight streams through stained glass windows depicting the life of a black Jesus. The Reverend Doctor Jeremiah A. Wright Jr., Trinity’s pastor since 1972, flies a red, black, and green flag near his altar and often preaches in a dashiki. He has spent decades writing about the African roots of Christianity, partly as a way to convince young blacks tempted by Islam that Christianity is not “a white man’s religion.”

On this particular Sunday, the sea of black worshippers is dotted with a few white folks up in the balcony, clutching copies of The Audacity of Hope they’ve brought for Obama’s book-signing later. Obama, sitting in the third row with his wife and two daughters, Malia and Natasha, stands, claps, prays, and sways along with the rest of the congregation. During the sermon, he watches the preacher carefully and writes notes. When asked by Wright to say a few words, Obama grabs the microphone and stands. “I love you all,” he says. “It’s good to be back home.” The 150-person choir breaks into a chorus of “Barack, Hallelujah! Barack, Hallelujah!”

This adulation is a far cry from how Obama was received by Wright when they first met in the mid-’80s, during Obama’s initial roundof one-on-ones. Like Smalls, Wright was unimpressed. “They were going to bring all different denominations together to have this grassroots movement,” explained Wright, a white-haired man with a goatee and a booming voice. “I looked at him and I said, ‘Do you know what Joseph’s brother said when they saw him coming across the field?’” Obama said he didn’t. “I said, ‘Behold the dreamer! You’re dreaming if you think you are going to do that.’”

From Wright and others, Obama learned that part of his problem as an organizer was that he was trying to build a confederation of churches but wasn’t showing up in the pews on Sunday. When pastors asked him the inevitable questions about his own spiritual life, Obama would duck them uncomfortably. A Reverend Philips put the problem to him squarely when he learned that Obama didn’t attend services. “It might help your mission if you had a church home,” he told Obama. “It doesn’t matter where, really. What you’re asking from pastors requires us to set aside some of our more priestly concerns in favor of prophesy. That requires a good deal of faith on our part. It makes us want to know just where you’re getting yours from.”

After many lectures like this, Obama decided to take a second look at Wright’s church. Older pastors warned him that Trinity was for “Buppies”—black urban professionals—and didn’t have enough street cred. But Wright was a former Muslim and black nationalist who had studied at Howard and Chicago, and Trinity’s guiding principles—what the church calls the “Black Value System”—included a “Disavowal of the Pursuit of ‘Middleclassness.’”

The cross currents appealed to Obama. He came to believe that the church could not only compensate for the limitations of Alinsky-style organizing but could help answer the nagging identity problem he had come to Chicago to solve. “It was a powerful program, this cultural community,” he wrote, “one more pliant than simple nationalism, more sustaining than my own brand of organizing. “

As a result, over the years, Wright became not only Obama’s pastor, but his mentor. The title of Obama’s recent book, The Audacity of Hope, is based on a sermon by Wright. (It’s worth noting, however, that, while Obama’s book is a cool headed appeal for common ground in an age of political polarization, Wright’s sermon, “The Audacity to Hope,” is a fiery jeremiad about persevering in a world of nuclear arms and racial inequality.) Wright is one of the first people Obama thanked after his Senate victory in 2004, and he recently name-checked Wright in his speech to civil rights leaders in Selma, Alabama.

The church also helped Obama develop politically. It provided him with new insights about getting people to act, or agitating, that his organizing pals didn’t always understand. “It’s true that the notion of self-interest was critical,” Obama told me. “But Alinsky understated the degree to which people’s hopes and dreams and their ideals and their values were just as important in organizing as people’s self-interest.” He continued, “Sometimes the tendency in community organizing of the sort done by Alinsky was to downplay the power of words and of ideas when in fact ideas and words are pretty powerful. ‘We hold these truths to be self-evident, all men are created equal.’ Those are just words. ‘I have a dream.’ Just words. But they help move things. And I think it was partly that understanding that probably led me to try to do something similar in different arenas.”

In 1995, Obama shocked his old friend Jean Rudd by telling her he wanted to run for the state Senate. Back in 1985, Rudd, then working at the Woods Fund—a Chicago foundation that gives grants for community organizing—had provided Kellman with his original $25,000 to hire Obama. When Obama returned to Chicago to practice law, he joined the board of Rudd’s foundation. Now he was going to the other side. “That’s a switch!” she told him. Obama insisted that nothing would change. “Oh no,” he said, according to Rudd. “I’m going to use the same skills as a community organizer.”

In fact, Obama had already been applying Alinsky’s core concepts—rigorous analysis of an opponent’s strengths, a hardheaded understanding of self-interest as a fundamental organizing principle, a knack for agitating people to act, and a streetwise sense of when a raw show of power is necessary—to situations beyond the South Side. In 1988, Obama left Chicago for Harvard Law, where his greatest political victory was getting himself elected president of the law review. He did it by convincing a crucial swing bloc of conservatives that their self-interests would be protected by electing him. He built that trust during the same kind of long listening sessions he had made use of in the depressed neighborhoods of Chicago. “He didn’t get to be president of Harvard Law Review because he was first in his class,” said Richard Epstein, a colleague of Obama’s at the University of Chicago Law School, where Obama later taught. “He got it because people on the other side believed he would give them a fair shake.”

Even at Harvard, Obama kept a foot in the world of organizing. He spent eight days in Los Angeles taking a national training course taught by the IAF, a station of the cross for Alinsky acolytes. And, after he returned to Chicago in 1991, he served on the boards of both the Woods Fund and the Joyce Foundation, which also gives grants to Alinsky-style groups, and continued to teach organizing workshops.

In 1992, he got a taste of the relationship between organizing and electoral politics when he led a voter registration drive that helped Carol Moseley Braun become the first black woman ever elected to the Senate. By 1995, he laid out his vision of the agitator-politician in an interview with the Chicago Reader: “What if a politician were to see his job as that of an organizer, as part teacher and part advocate, one who does not sell voters short but who educates them about the real choices before them? As an elected public official, for instance, I could bring church and community leaders together easier than I could as a community organizer or lawyer.”

This high-minded mission statement, however, obscures the real-world organizing skills that proved relevant to Obama’s political career. They surface in the story of his first campaign. Obama initially planned to inherit the seat of a much-admired incumbent named Alice Palmer, a fixture in South Side activist circles since the ‘60s. Palmer had opted to run for Congress, clearing the way for Obama to replace her, but, when she lost the primary, she decided she wanted to keep her old Senate seat, after all.

Obama was faced with a decision: step aside and wait his turn or do everything he could to take down a popular incumbent. In one meeting, an old guard of black political leaders tried to force Obama to abandon the race, but he wouldn’t budge. Instead of deferring to Palmer’s seniority, Obama challenged the very legitimacy of her petitions to get on the ballot, dispatching aides to the Chicago Board of Elections to scour Palmer’s filing papers, and, while they were at it, every other candidate’s, signature by signature. Many were fake. Obama won the challenge and cleared not just Palmer but all his potential rivals from the field.

It was a brash maneuver that caught the attention of the Illinois political establishment. “His introduction to the political community was that he knocked off Alice,” said Ron Davis, a longtime Obama political hand who filed the challenge against Palmer and still cackles with glee over their victory. “The[current] president of the state Senate, Emil Jones, pushed very hard to save Alice, but we beat his staff. So they heard about Barack before he came down there to Springfield: ‘Who was this guy who came in and knocked Alice off the ballot?’”

In the wake of Obama’s recent contretemps with the Clinton campaign—she asked him to return money raised by Hollywood mogul David Geffen after Geffen had some acid words for her in the press; Obama declined—this episode acquires added resonance. The core question being raised today about Obama the candidate is whether he can be both a post-partisan, inspirational figure—the dreamer whom Wright first identified—and also the type of uncompromising political realist who can actually win. After all, the presidential campaign trail is littered with candidates, from Adlai Stevenson to Bradley, who, like Obama, bemoaned the dirty business that politics has become and tried to run campaigns that rose above the muck. Such candidates may maintain the high ground, but they always lose. Obama’s assertion that he is, at heart, a community organizer suggests he might not fall into the same trap. He was, after all, trained to pursue the ideal but practice the pragmatic. Obama internalized the Alinsky maxim to always live in “the world as it is and not as we would like it to be,” and, starting with his race against Palmer, he put it to use. In the world as we would like it to be, every election should have more than one contestant. In the world as it is, especially in Chicago, you challenge your opponents’ signatures and knock them off the ballot.

The Palmer race was one of the earliest clues that Obama’s sincere critique about what’s wrong with politics should not be mistaken for a declaration of unilateral disarmament when it comes to campaigning. He is not running a protest campaign like Jerry Brown’s in 1992, or one under the delusion that it is above politics, like Bradley’s. He is operating in the world as it is. When I asked Ron Davis if Obama is too idealistic, he laughed. “Barack knows how to play the game!” he told me. “I would hope we would not have a pie-in-the-sky type for president. These are not the times.” Galluzzo concurred: “First of all, he’s committed to his values. They are not bullshit to him. He personally believes the principles he’s espousing. Now, do I also believe he’s ambitious and will do whatever it takes to win? Yes.”

Speaking of what he learned as an organizer, Obama himself told me,”I think that often times ordinary citizens are taught that decisions are made based on the public interest or grand principles, when, in fact, what really moves things is money and votes and power.”

After beating Palmer, Obama brought some of his old organizing lessons to Springfield. His successful career there owed much to a relationship he built with Emil Jones, the South Side machine pol whom Obama later described as his “political godfather.” Jones was an improbable mentor for Obama: In the mid-’80s, Obama’s group had organized protests against Jones when it wanted more help with funding for its projects. In Dreams, Obama portrayed Jones as an “old ward heeler” jockeying for position on a stage with the mayor. And Obama and Jones tangled over Alice Palmer, whom Jones had tried to rescue. Yet despite that history, or perhaps because of it, Obama sought out Jones in the legislature and let him know he was eager to work with him. Jones’s mentoring frayed Obama’s relationships with some other black colleagues—“petty jealousies,” Jones told me—but it paved the way for all of Obama’s legislative achievements.

“Emil was then, and is now, a powerhouse,” Rudd told me. “One of the things that community organizing teaches you is to do something called power analysis. You have to understand how to have a relationship with people in power, to be a peer with them, not to go on your knees begging but understand yourself as a co-equal and find a way that someone who has power will understand your power. That’s the whole point of organizing: What is it that people in power need to accommodate your needs?”

In 2000, Obama challenged Representative Bobby Rush, a former Black Panther whose connection to black Chicago once seemed unshakable. But, after Rush tried and failed to dislodge Richard M. Daley from the mayor’s office in 1999, Obama saw an opening. The contest proved particularly painful for him when his opponents picked at old wounds about his identity. Donne Trotter, another candidate and state Senate rival who resented Obama’s meteoric rise, told The Chicago Reader, “Barack is viewed in part to be the white man in blackface in our community.” But those accusations probably had more impact on Obama emotionally than they did on his poll numbers. A few months before the election, Rush’s son was shot and killed during a robbery, creating a wave of sympathy that carried him to victory.

After his defeat, Obama doubled down on his efforts to secure Jones’s patronage. “When he ran for the U.S. House and lost that race, he learned from that,” Jones told me. “He recognized that, even though you feel it in yourself that you are the best person, you need others around you that can influence others in support of you—or keep some people from being obstructionists. You need people to open doors for you. I guess that’s what he saw in me.”

There was another door Obama thought Jones could open. When the Democrats took over the Illinois Senate in 2003, Obama paid Jones a visit. “After I was elected president, he came in to see me one day,” Jones told me. “He said, ‘You were just elected president. You have a lot of power now.’ ‘What kind of power do I have?’ He said, ‘You have the power to make a United States senator.’ ‘That sounds good. Do you have anybody in mind?’ He said, ‘Yeah, me.’”

Despite this history, Obama is still cast by the press as the candidate unwilling to stoop low enough to win, while Hillary is the machine politician whose last name has become synonymous with ruthlessness. But that David-versus- Goliath framing of the race is overstated. Obama’s political team is seasoned and conventional. His media adviser and strategic guru, David Axelrod, has spent decades in Chicago politics working for both the reformers (Harold Washington) and the machine (Richard M. Daley). Obama has all of the political machinery—ad-makers, fund-raisers, opposition-researchers—in place to run a serious but traditional campaign.

Moreover, when Obama’s ideals clash with reality, he has been able to find compromises that don’t put him at a political disadvantage. For instance, no Democrat can win the general election while adhering to the public financing system if the Republican nominee doesn’t do the same. Clinton and John Edwards have simply conceded that the public financing system is dead and are ignoring fund-raising restrictions that would be triggered if either ends up playing within the public financing scheme. Facing the same situation, Obama—a longtime champion of campaign finance reform in general and public financing in particular—asked the Federal Election Commission if he could raise the potentially restricted money now (the world as it is) but then give it back if he wins the nomination and convinces his Republican opponent to stick with public financing (the world as we would like it to be).

Back home in Chicago’s recent mayoral election, Obama endorsed Richard M. Daley—the symbol of machine politics, corruption, and racism for Hyde Park progressives and Obama’s old organizing friends. Asked if she was disappointed, Rudd said, “Yeah. We all want our politicians to be pure and ideological, but I think it was a strategic move on his part and a well-considered one.” Another member of Obama’s organizing fraternity told me, “That’s part of his political savvy. ... He recognizes that Daley is a powerful man and to have him as an ally is important. While he was a state senator here and moving around in Chicago, he made sure to minimize the direct confrontational approach to people of influence and policymakers and civic leaders. These are the same people now who are very aggressively supporting his campaign.”

But when those supporters become a liability, Obama has not been afraid to take a direct, confrontational approach. Reverend Wright learned this recently, on the evening before he was scheduled to deliver the invocation at Obama’s presidential announcement speech in Springfield. According to The New York Times, after Trinity’s Afrocentrism—which had originally drawn Obama to the church in the 1980s—had become a sticky campaign issue, Obama called his old friend and told him it was probably best if the pastor didn’t speak, after all. The following day, Wright could be seen silently watching the proceedings from the sidelines along with other Obama supporters.

The way that Obama and his team have responded to the opening skirmishes of the presidential race has also been telling. Every time Obama has been challenged this year, his campaign has responded with ferocity. When Fox News falsely reported that Obama attended a madrassa in Indonesia, his aides not only went into war-room mode, beating back the story—not that difficult, considering it was obviously untrue—but Robert Gibbs, Obama’s communications director, also told Fox political reporter Carl Cameron that he wouldn’t be allowed to travel on Obama’s plane. What is Fox going to do to us, Gibbs asked Cameron, report that Obama attended a radical Islamic school? Oh, wait, you already did that!

When Australian Prime Minister John Howard said Obama’s Iraq plan would embolden Al Qaeda, Obama delivered a rehearsed line to a room full of reporters about how Howard should send more Aussies to Iraq if he cares so much about the situation there. And, most famously,when the Clinton campaign called on Obama to distance himself from Geffen, his campaign shot back by referencing the Clintons’ Lincoln Bedroom fund-raising scandal.

In our last conversation, a few days after the Geffen episode, I asked Obama if his reputation for purity is a little overblown. He chuckled. “I wouldn’t be a U.S. senator or out of Chicago or a presidential candidate from Illinois if I didn’t have some sense of the world as it actually works,” he said. “When I arrived in Chicago at the age of twenty-four, I didn’t know a single person in Chicago, and I know an awful lot of folks now. And so, obviously, some of that has to do with me being pretty clear-eyed about power.”

But being clear-eyed about power also means understanding its limits.

“What I am constantly trying to do,” he added, “is balance a hard head with a big heart.”

By Ryan Lizza