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The Political Scene

Making It

How Chicago shaped Obama.

by Ryan Lizza

July 21, 2008



Barack Obama on the South Side during his first campaign, for the State Senate. An outsider in Chicago’s system, he was meticulous about constructing his own political identity and coalition. Photograph by Marc PoKempner.
Barack Obama on the South Side during his first campaign, for the State Senate.
An outsider in Chicago’s system, he was meticulous about constructing his own
political identity and coalition. Photograph by Marc PoKempner.

One day in 1995, Barack Obama went to see his alderman, an influential politician named Toni Preckwinkle, on Chicago’s South Side, where politics had been upended by scandal. Mel Reynolds, a local congressman, was facing charges of sexual assault of a sixteen-year-old campaign volunteer. (He eventually resigned his seat.) The looming vacancy set off a fury of ambition and hustle; several politicians, including a state senator named Alice Palmer, an education expert of modest political skills, prepared to enter the congressional race. Palmer represented Hyde Park—Obama’s neighborhood, a racially integrated, liberal sanctuary—and, if she ran for Congress, she would need a replacement in Springfield, the state capital. Obama at the time was a thirty-three-year-old lawyer, university lecturer, and aspiring office-seeker, and the Palmer seat was what he had in mind when he visited Alderman Preckwinkle.

“Barack came to me and said, ‘If Alice decides she wants to run, I want to run for her State Senate seat,’ ” Preckwinkle told me. We were in her district office, above a bank on a street of check-cashing shops and vacant lots north of Hyde Park. Preckwinkle soon became an Obama loyalist, and she stuck with him in a State Senate campaign that strained or ruptured many friendships but was ultimately successful. Four years later, in 2000, she backed Obama in a doomed congressional campaign against a local icon, the former Black Panther Bobby Rush. And in 2004 Preckwinkle supported Obama during his improbable, successful run for the United States Senate. So it was startling to learn that Toni Preckwinkle had become disenchanted with Barack Obama.

Preckwinkle is a tall, commanding woman with a clipped gray Afro. She has represented her slice of the South Side for seventeen years and expresses no interest in higher office. On Chicago’s City Council, she is often a dissenter against the wishes of Mayor Richard M. Daley. For anyone trying to understand Obama’s breathtakingly rapid political ascent, Preckwinkle is an indispensable witness—a close observer, friend, and confidante during a period of Obama’s life to which he rarely calls attention.

Although many of Obama’s recent supporters have been surprised by signs of political opportunism, Preckwinkle wasn’t. “I think he was very strategic in his choice of friends and mentors,” she told me. “I spent ten years of my adult life working to be alderman. I finally got elected. This is a job I love. And I’m perfectly happy with it. I’m not sure that’s the way that he approached his public life—that he was going to try for a job and stay there for one period of time. In retrospect, I think he saw the positions he held as stepping stones to other things and therefore approached his public life differently than other people might have.”

On issue after issue, Preckwinkle presented Obama as someone who thrived in the world of Chicago politics. She suggested that Obama joined Jeremiah Wright’s Trinity United Church of Christ for political reasons. “It’s a church that would provide you with lots of social connections and prominent parishioners,” she said. “It’s a good place for a politician to be a member.” Preckwinkle was unsparing on the subject of the Chicago real-estate developer Antoin (Tony) Rezko, a friend of Obama’s and one of his top fund-raisers, who was recently convicted of fraud, bribery, and money laundering: “Who you take money from is a reflection of your knowledge at the time and your principles.” As we talked, it became increasingly clear that loyalty was the issue that drove Preckwinkle’s current view of her onetime protégé. “I don’t think you should forget who your friends are,” she said.

Others told me that Preckwinkle’s grievances against Obama included specific complaints, such as his refusal to endorse a former aide and longtime friend, Will Burns, in a State Senate primary—a contest that Burns won anyway. There was also a more general belief that, after Obama won the 2004 United States Senate primary, he ignored his South Side base. Preckwinkle said, “My view is you have to bring your constituency along with you. Granted, you have to make some tough decisions. Granted, sometimes you have to make decisions that people won’t understand or like. But it’s your obligation to explain yourself and try to do your supporters the courtesy of treating them with respect.” Ivory Mitchell, who for twenty years has been the chairman of the local ward organization in Obama’s neighborhood—considered the most important Democratic organization on the South Side—was one of Obama’s earliest backers. Today, he says, “All the work we did to help him get where he finally ended up, he didn’t seem too appreciative.” A year ago, Mitchell became a delegate for Hillary Clinton.

The same month Mitchell endorsed Clinton, the Obama campaign reached out to Preckwinkle, and eventually she signed on as an Obama delegate. I asked her if what she considered slights or betrayals were simply the necessary accommodations and maneuvering of a politician making a lightning transition from Hyde Park legislator to Presidential nominee. “Can you get where he is and maintain your personal integrity?” she said. “Is that the question?” She stared at me and grimaced. “I’m going to pass on that.”





Obama likes to discuss his unusual childhood—his abandonment by his father and his upbringing by a sometimes single mother and his grandparents in Indonesia and Hawaii—and the three years in the nineteen-eighties when he worked as a community organizer in Chicago, periods of his life chronicled at length in his first memoir, “Dreams from My Father.” He occasionally refers to his time in the United States Senate, which he wrote about in his second memoir, “The Audacity of Hope.” But his life in Chicago from 1991 until his victorious Senate campaign is a lacuna in his autobiography. It is also the period that formed him as a politician. Some Obama supporters professed shock when, recently, he abandoned a pledge to stay within the public campaign-finance system if the presumptive Republican nominee, Senator John McCain, agreed to do the same. Preckwinkle’s concern about Obama—that he is a pure political animal—suddenly became more widespread; commentators abruptly stopped using the words “callow” and “naïve.”

Chicago is not Obama’s home town, but it’s where he chose to forge his identity. Several weeks ago, he moved many of the Democratic National Committee’s operations from Washington to Chicago, making the city the unofficial capital of the Democratic Party; his campaign headquarters are in an office building in the Loop, Chicago’s downtown business district. But Chicago, with its reputation as a center of vicious and corrupt politics, may also be the place that Obama needs to leave behind.

Simply moving there, as he did after graduating from Harvard Law School, was a bold decision. Chicago, where the late mayor Richard J. Daley and his son, the current mayor, have governed for forty out of the past fifty-three years, is not hospitable to political carpetbaggers. Abner Mikva, who was a congressman from Hyde Park and later the chief judge on the Washington, D.C., Circuit Court, was one of the first Chicago politicians to successfully challenge the Daley machine, and it took him years to overcome people’s skepticism about his Wisconsin roots. Mikva, who is now eighty-two, tried to recruit Obama to work for him in Washington as a law clerk. Obama turned him down, replying that he was returning to Chicago to run for office. “I thought, Boy, does he got something to learn,” Mikva told me recently. “You just don’t come to Chicago and plant your flag.”

I met Mikva at the Cliff Dwellers, a private dining club atop a downtown office building. As we looked out over Lake Michigan, he told me a story that has often been repeated by others to capture the essence of politics in the city. “When I first came to Chicago, Adlai Stevenson and Paul Douglas were running for governor and senator,” he said. “I had heard about the closed Party, closed machine, but they sounded like such great candidates, so I stopped in to volunteer in the Eighth Ward Regular Democratic headquarters. I said, ‘I’m here for Douglas and Stevenson.’ The ward boss came in and pulled the cigar out of his mouth and said, ‘Who sent you?’ And I said, ‘Nobody sent me.’ He put the cigar back in his mouth and said, ‘We don’t want nobody nobody sent.’ ”

There was another tradition in Chicago politics, the so-called Independents, which grew up in opposition to Richard J. Daley—Boss Daley—whose reign lasted from 1955 to 1976. Anchored in Hyde Park and nurtured by the University of Chicago community, the Independents brought together African-Americans and white liberals in coalitions that became the city’s main alternative to the Democratic machine. The Independents arose after the Second World War to challenge the closed patronage system that controlled the city, and became a serious political force in the mid-nineteen-fifties. Their numbers increased with a new wave of black activists energized by Martin Luther King, Jr.,’s Chicago organizing in 1966, and with white liberals outraged when antiwar protesters were beaten and teargassed by Chicago police during the Democratic National Convention in 1968.

Mayor Daley died in office in 1976, at the age of seventy-four. He was replaced by a reliable and ineffectual machine candidate, Michael Bilandic, whose appointment marked the beginning of twelve years of chaotic, balkanized politics, sometimes called the “inter-Daley period.” David Axelrod, who has been Obama’s chief strategist since 2002 and is the foremost political consultant in Chicago, was a witness to all of it, first as a political reporter for the Chicago Tribune and later as the chief consultant to two mayors: Harold Washington, Chicago’s first black mayor and a hero of the Independents, and the current Mayor Daley, whose last name still carries negative connotations in the precincts of Hyde Park. Axelrod, who is fifty-three, is by nature subdued. He wears a mustache that curls down the sides of his upper lip in a permanent expression of melancholy. We met in a Houlihan’s, off the lobby of the building that houses the Obama campaign headquarters.

Axelrod recalled the election, in 1979, of Jane Byrne, Chicago’s first female mayor, which he wrote about for the Tribune. Byrne’s campaign, assisted by snowstorms that shut down the city and showcased Bilandic’s incompetence, was the first successful insurgency in modern Chicago history. “It was a great reform campaign,” Axelrod said. “I then chronicled, for the next four years, her systematic abrogation of every commitment she had made to reform. She became sort of a parody of a machine mayor.” In office, Byrne aligned herself with City Council officials who were hostile to the city’s black leadership, pandered to the voters of the most racist wards of the city, and purged African-Americans from key positions. On the South Side, there was a backlash; Washington, who had run a spirited campaign for mayor in 1977, was elected to Congress in 1980. In 1983, he was essentially drafted by a Hyde Park-based coalition desperate to unseat the disappointing Byrne. Washington won a three-way primary, with thirty-six per cent of the vote, and went on in the general election to defeat a white Republican who ran, briefly, on the implicitly racist slogan “Before it’s too late.” Washington’s first term was dominated by warfare with a City Council controlled by white aldermen determined to stymie every proposal. But in 1986 he took control of the council and the following year was reëlected. Seven months after his victory, he collapsed at his desk, dead of a heart attack at the age of sixty-five. Axelrod saw much of this history from the inside, as Washington’s strategist; Obama saw it from the perspective of an organizer who occasionally had brushes with the powerful at political events or meetings at City Hall. “He saw the jagged edges of Chicago politics and urban politics pretty close up,” Axelrod said.

Obama spent three years in the city, from 1985, after he graduated from Columbia University, to the end of the Washington era. As a community organizer, he tried to turn a partnership of churches into a political force on the South Side. But the work accomplished very little.

“When I started organizing, I understood the idea of social change in a very abstract way,” Obama told me last year. “It was to some extent informed by my years in Indonesia, seeing extreme poverty and disparities of wealth and understanding sort of in a dim way that life wasn’t fair and government had something to do with it. I understood the role that issues like race played and took inspiration from the civil-rights movement and what the student sit-ins had accomplished and the freedom rides.

“But I didn’t come out of a political family, didn’t have a history of activism in my family. So I understood these things in the abstract. When I went to Chicago, it was the first time that I had the opportunity to test out my ideas. And for the most part I would say I wasn’t wildly successful. The victories that we achieved were extraordinarily modest: you know, getting a job-training site set up or getting an after-school program for young people put in place.”





In 1988, Obama left for Harvard Law School, returning to Chicago twice for summer stints at élite law firms, including, after his first year, Sidley Austin. (Sidley Austin is where he met Michelle Robinson, whom he married in 1992.) He returned to Chicago permanently when he graduated, in 1991. In a short period, he built a notable résumé and a network of connections. During the 1992 Presidential campaign, he ran a voter-registration drive that placed him at the center of the city’s politics. That year, Illinois elected the first African-American woman to the U.S. Senate, Carol Moseley Braun, and Bill Clinton became the first Democratic Presidential candidate to carry Illinois since Lyndon Johnson, in 1964. Meanwhile, Obama practiced civil-rights law at a firm admired in the city’s progressive circles, and became a popular lecturer in the law school at the University of Chicago. He was on the board of two liberal foundations that spread grant money around Chicago, and he settled in Hyde Park.

It was a neighborhood in transition when Obama arrived. The Hyde Park Herald serves as a sort of time capsule. It reported that crime was rising; a series of violent robberies was another reminder that Hyde Park existed as a middle-class island in a sea of high-crime urban poverty. New data showed that white enrollment was steeply declining at one local school. During the Martin Luther King, Jr., celebrations, the newspaper noted in passing that Jeremiah Wright was scheduled to give a speech at the University of Chicago. Considerable coverage was given to two institutions: the local food co-op, where Obama shopped every Saturday, and the Independent Voters of Illinois–Independent Precinct Organization, or I.V.I.-I.P.O., one of the neighborhood’s most influential political groups. There was a new political force in Hyde Park as well. Real-estate developers were swooping in to rehabilitate low-income housing. On more than one occasion, the Hyde Park Herald reported on the rise in campaign donations from these developers to South Side politicians; in 1995, it ran a front-page article about Tony Rezko, who was then a very active new donor on the scene.

While it’s true that nobody sent Obama in the sense that Abner Mikva meant it, one of Obama’s underappreciated assets, as he looked for a political race in the early nineties, was the web of connections that he had established. “He understands how you network,” Mikva said. “I remember our first few meetings. He would say, ‘Do you know So-and-So?’ And I’d say yes. ‘How well do you know him? I’d really like to meet him.’ I would set up some lunches.”

The 1992 voter-registration drive, Project Vote, introduced him to much of the city’s black leadership. “If you want to look at the means of ascent, if you will, look at Project Vote,” Will Burns, the former Obama aide, said. In Chicago progressive circles, Burns, who is thirty-four, is described as an up-and-coming African-American legislator in the Obama tradition. Obama’s refusal to endorse Burns in his primary earlier this year infuriated and mystified a number of Chicago Democrats, though Burns himself displays no bitterness and is now an adviser to the Obama campaign.

At Project Vote, Burns said, Obama “was making connections at the grassroots level and was working with elected officials. That’s when he first got a scan of the broader black political infrastructure.” It was also the beginning of a dynamic that stood out in Obama’s early career: his uneasy relationship with an older generation of black Chicago politicians. Project Vote “is where a lot of the divisional rivalries popped up,” Burns said.

In this early foray into politics, Obama revealed the toughness and brashness that this year’s long primary season brought into view. As Burns, who has a mischievous sense of humor and a gift for mimicry, recalled, “Black activists, community folks, felt that he didn’t respect their role”—Burns imitated a self-righteous activist—“in the struggle and the movement. He didn’t engage in obeisance to them. He wanted to get the job done. And Barack’s cheap, too. If you can’t do it and do it in a cost-effective manner, you’re not going to work with him.” Ivory Mitchell, the ward chairman in Obama’s neighborhood, says of Obama that “he was typical of what most aspiring politicians are: self-centered—that ‘I can do anything and I’m willing to do it overnight.’ ”

During Project Vote, Obama also began to understand the larger world of Chicago’s liberal fund-raisers. “He met people not just in the African-American community but in the progressive white community,” David Axelrod said. “The folks who funded Project Vote were some of the key progressive leaders.” Obama met Axelrod through one of Project Vote’s supporters, Bettylu Saltzman, whose father, Philip M. Klutznick, was a Chicago shopping-mall tycoon, a part owner of the Bulls, and a former Commerce Secretary in the Carter Administration. Saltzman, a soft-spoken activist who worked for Senators Adlai E. Stevenson III and Paul Simon, took an immediate interest in Obama. “I honestly don’t remember what it was about him, but I was absolutely blown away,” Saltzman says. “I said to several people that this guy, who is now thirty years old, is someday going to be President. He will be our first black President.”

Obama’s legal career helped bring him into Chicago’s liberal reform community. In 1993, after he finished his work with Project Vote and was seeking to join a law firm, instead of returning to Sidley Austin he took a job at Davis, Miner, Barnhill & Galland, a boutique civil-rights firm led by Harold Washington’s former counsel, Judson Miner. Miner had perfect anti-Daley credentials, routinely filing lawsuits against the city, and was a founding member of the Chicago Council of Lawyers, which was to Chicago’s legal élite what the Independents were to the Democratic machine.

Working at Davis, Miner enhanced Obama’s profile. “When you go work for Judd Miner’s law firm, that’s another kind of political statement,” Don Rose, a longtime Chicago political consultant, who ran Jane Byrne’s campaign, told me. Will Burns said, “I think it might have been helpful with a certain group of people that Barack may have wanted to have at his back at the outset. So you get the support of the liberals and the progressives and the reformers, and then that gives you a base to then expand to pick up other folks. And then folks would be willing to give money to the bright, shiny new candidate.” Joining Miner’s firm, like living in Hyde Park, was a way of choosing sides in the city’s long-running political battle between the machine and the Independents. Toni Preckwinkle explained Miner’s legal work this way: “They’ve shown a remarkable willingness to take on the Democratic organization and the Democratic establishment in this city and win. Which is why I like them and a lot of people hate them.”

If Project Vote and Miner’s firm introduced Obama to the city’s lakefront liberals and South Side politicians, it was his wife who helped connect him to Chicago’s black élite. One of Michelle’s best friends was Jesse Jackson’s daughter Santita, who became the godmother of the Obamas’ first child. Michelle had worked as an aide to the younger Daley—hired by Valerie Jarrett, who is now one of Obama’s closest advisers. (Jarrett, an African-American, was born in Iran, where her father, a doctor, helped run a hospital; she and Obama formed a bond over their unusual biographies.) It was also through Michelle that Obama met Marty Nesbitt, a successful young black entrepreneur who happened to play basketball with Michelle’s brother, Craig. (Nesbitt’s wife, Anita Blanchard, an obstetrician, delivered the Obamas’ two daughters.) Nesbitt became Obama’s closest friend and a bridge to the city’s African-American business class.

Obama seems to have been meticulous about constructing a political identity for himself. He visited churches on the South Side, considered the politics and reputations of each one, and received advice from older pastors. Before deciding on Trinity United Church of Christ, he asked the Reverend Wright about critics who complained that the church was too “upwardly mobile,” a place for buppies. Though he admired Judson Miner, he was similarly cautious about joining his law firm. Miner once told me that it took “a series of lunches” and hours of discussion before Obama made his decision. At the time, Obama was working on “Dreams from My Father.”

Many have said that part of the appeal of “Dreams” is its honesty, pointing out that it was written at a time when Obama had no idea that he would run for office. In fact, Obama had been talking about a political career for years, musing about becoming mayor or governor. According to a recent biography of Obama by the Chicago Tribune reporter David Mendell, he even told his future brother-in-law, Craig Robinson, that he might run for President one day. (Robinson teased him, saying, “Yeah, yeah, okay, come over and meet my Aunt Gracie—and don’t tell anybody that!”) Obama was writing “Dreams” at the moment that he was preparing for a life in politics, and he launched his book and his first political campaign simultaneously, in the summer of 1995, when he saw his first chance of winning.

Many people who knew Obama then remember him for his cockiness. He had good reason to be self-assured. A number of his accomplishments had been accompanied by adoring press coverage. When he was named president of the Harvard Law Review, in 1990, he was profiled by, among others, the Times, the Boston Globe, the Los Angeles Times, the Chicago Tribune, Vanity Fair, and the Associated Press. Even then, the essential elements of Obama-mania were present: the fascination with his early life, the adulatory quotes from friends who thought that he would be President one day, and Obama’s frank, though sometimes ostentatious, capacity for self-reflection. (“To some extent, I’m a symbolic stand-in for a lot of the changes that have been made,” he told the Boston Globe in 1990.)

His work for Project Vote was similarly applauded. In 1993, Crain’s Chicago Business reported that Obama had “galvanized Chicago’s political community, as no seasoned politico had before,” and an alderman told Crains, “Under Barack’s leadership, we had the most successful, cost-effective and orderly voter registration drive I’ve ever been involved with.” When “Dreams from My Father” was published, the reviews were overwhelmingly positive; Booklist included the memoir in a “guide to some of the best books of 1995.”

Obama knew that Hyde Park, despite its reputation as the center of anti-machine progressives, was not exempt from other Chicago political traditions. During the first half of 1995, when he was preparing for his campaign for the State Senate, a big story in the neighborhood was a race for alderman marked by accusations of dirty tricks (endorsement flyers from a phony group of gay African-Americans were distributed the day before the election, apparently in an effort to stoke homophobia) and anti-Semitism (the campaign of one of the candidates was accused of being run by “Jewish overseers”).





Obama’s campaign began without much excitement. He had ties to so many of the city’s élite factions that the local press described him as “a well-connected attorney.” In August, the Chicago Sun-Times noted that Valerie Jarrett was hosting “a private autograph party” for Obama. His memoir was turning him into a figure of some acclaim. The same month, the Hyde Park Herald, which later called the book “a local indie hit,” ran a flattering profile that highlighted a theme from “Dreams”: how Chicago helped Obama end a long journey of self-discovery, a narrative that helped defuse any notion that Obama was a carpetbagger. “I came home in Chicago,” he told the newspaper. “I began to see my identity and my individual struggles were one with the struggles that folks face in Chicago.”

A month later, on September 19th, Obama invited some two hundred supporters to a lakefront Ramada Inn to announce his candidacy for the State Senate, and some of what he said sounded very much like the Obama of recent months. “Politicians are not held to highest esteem these days,” he told the crowd. “They fall somewhere lower than lawyers. . . . I want to inspire a renewal of morality in politics. I will work as hard as I can, as long as I can, on your behalf.” Alice Palmer introduced Obama, and an account in the Hyde Park Herald quoted more from her speech than from his; it was, after all, chiefly her endorsement that certified him as a plausible candidate. “In this room, Harold Washington announced for mayor,” Palmer said. “Barack Obama carries on the tradition of independence in this district. . . . His candidacy is a passing of the torch.”

Also in attendance that day were Toni Preckwinkle and Will Burns, who was then a recent University of Chicago graduate. (He went on to get a master’s in social sciences; Obama helped persuade him to leave the university before he got a Ph.D., telling him, “You shouldn’t be too academic.”) Obama’s talk of a “renewal of morality in politics,” which previewed themes that emerged in this year’s campaign, also tapped into a desire for generational change—similarly consistent with his current rhetoric. He was able to capture the imagination of some young African-Americans frustrated by their local leadership. Burns said, “You have to understand, it’s 1995. It’s the year after the Republicans have taken over control of Congress, and in Illinois all three branches of government were also controlled by the Republicans. So it was a really dark point. I was looking to be engaged in something that would mean something, that would actually get something done and that was beyond symbols. Around the same time that I started up with Barack, volunteering on his campaign, I had gone to some of the old community groups and nationalist organizations. I respected what they had done, but I didn’t feel like that was really where I wanted to be.”

However, the campaign was no insurgency. Obama abided by the local way of doing things. He had lined up support from Preckwinkle, his alderman, and Ivory Mitchell, the local ward chairman, and Palmer’s endorsement brought with it two organizational assets: local operators and local activists. The operators helped Obama get on the ballot and handled the mechanics of his election. Two key operators were Alan Dobry and his wife, Lois Friedberg-Dobry, then in their late sixties and leaders of the Independent movement. “When you go to a political meeting, and you see a couple of guys or girls at the back of the room, and they aren’t glad-handing or anything, those are the operators,” Alan Dobry told me recently. There was a machinelike quality to the way the campaign unfolded. Palmer’s endorsement was the only signal that the Dobrys needed to start the slow, detailed organizing necessary to win a State Senate seat for Obama, whom they had never met, though they lived in his neighborhood.

Palmer’s imprimatur was also helpful with a small group of Hyde Park activists, some of whom she asked to hold fund-raising coffees for Obama. At her suggestion, Sam and Martha Ackerman, who were leaders of Independent Voters of Illinois, hosted a coffee at their home. Unlike the Dobrys, they insisted on a meeting with Obama before backing him, and their support was important enough for him to spend an hour with them in their dining room, submitting to an interview. Their reaction to him was a common one. “I don’t think he said he wanted to run for President, but he indicated that he was into public service for the long haul,” Martha Ackerman told me. “I remember very clearly I said to Sam, ‘If this guy is for real, he could be the first African-American President of the United States.’ ”

Bill Ayers and Bernadine Dohrn, another activist Hyde Park couple, also held an event for Obama. Forty years ago, Ayers and Dohrn were leaders of the Weathermen, the militant antiwar group that bombed the Pentagon and the United States Capitol. By the time Obama met Ayers, the former radical and onetime fugitive had been accepted into polite Chicago society and had been reborn as an education expert, eventually working as an informal adviser to Mayor Daley. (Those ties remain intact in the jumbled culture of Chicago politics. When Obama’s association with Ayers first became a campaign issue, Daley, whose father, in 1968, sent his police force into the streets to combat Ayers’s fellow-radicals, issued a statement praising Ayers as “a valued member of the Chicago community.”)

Obama seemed sure enough that he would win the State Senate primary, to be held in March, 1996—in Chicago, winning the primary is tantamount to winning the seat—to take time, late that summer, for a brief book tour, which started in Hyde Park and carried him as far as California. In October, he was one of the thousands of African-Americans from Chicago who travelled to Washington for the Million Man March. (Obama criticized the march, telling a local alternative newspaper that it was a waste of energy.) When he returned home, he had more immediate problems. In December, 1995, the South Side coalition that he had cobbled together began to fall apart. Palmer’s congressional campaign was eclipsed by her Democratic-primary opponents—Jesse Jackson, Jr., who had star power, and Emil Jones, a longtime leader in the State Senate. Several weeks before the primary, a group of her supporters—mostly older black activists, not unlike those Obama had tangled with when he was running Project Vote—realized that Palmer was destined for defeat and summoned him to a meeting. The Chicago Defender reported that Obama was asked “to step aside like other African Americans have done in other races for the sake of unity and to release Palmer from her commitment”—so that she could reclaim her State Senate seat. Obama left the meeting noncommittal.

Palmer was soundly defeated by Jackson—she got only ten per cent of the vote—and there were more insistent demands that Obama withdraw. He refused, which angered Palmer and her husband, Buzz. Buzz Palmer was a founder of the Afro-American Patrolman’s League, a reform group within the Chicago police department, and the couple had many ties to the city’s black leadership. Palmer, announcing that she had been drafted back into the State Senate race, went from being Obama’s most important supporter to his chief challenger; the woman who had launched his political career now threatened to end it. “That’s Chicago politics,” Obama told a reporter—with a sigh, the account said.

The South Side political community was forced to choose. The Ackermans went with Palmer, the Dobrys with Obama. Emil Jones announced his support for Palmer. Alderman Preckwinkle stayed with Obama. “I had given him my word I would support him,” she told me. “Alice didn’t forgive me, and she’s never going to forgive me.”

“These old nationalist guys start beating a drum—probably not the right metaphor—about how Barack should let this elder back in and how seniority’s important,” Burns said. “And they’re writing essays in the Defender and N’Digo”—another local paper covering Chicago’s black community. A comment in the Defender by Robert Starks, a professor of political science at Chicago’s Northeastern Illinois University and one of Palmer’s chief supporters, was typical: “If she doesn’t run, that seat will go to a Daley supporter. We have asked her to reconsider not running because we don’t think Obama can win. He hasn’t been in town long enough. . . . Nobody knows who he is . . . We need someone with experience.”

But, almost as fast as the threat to his campaign appeared, Obama stamped it out. The Dobrys were surprised that Palmer had so quickly gathered the signatures necessary to qualify for the ballot. They went to the Chicago board of elections and reviewed her petitions; as they suspected, they were filled with irregularities. One skill that the Independents had mastered in the years of fighting the first Mayor Daley was the machine’s tactic of challenging ballot petitions, and the Dobrys were experts at this Chicago ritual. Publicly, Obama was conciliatory about the awkward political situation, telling the Hyde Park Herald that he understood that some people were upset about the “conflict between old loyalties and new enthusiasms.” Privately, however, he unleashed his operators. With the help of the Dobrys, he was able to remove not just Palmer’s name from the ballot but the name of every other opponent as well. “He ran unopposed, which is a good way to win,” Mikva said, laughing at the recollection. And Palmer said last week, “Anyone who enters Chicago politics and can’t take the rough and tumble shouldn’t be there. Losing the seat was just that—not the end of the world.”

Instead of arriving in Springfield as the consensus candidate of his district, Obama was regarded as a troublemaker. “He had created some enemies,” Emil Jones, who in 2003 became president of the Illinois Senate, said. Burns described the fallout of the Obama-Palmer race this way: “It established a reputation that ‘you’re not going to punk me, you’re not going to roll me over, you’re not going to jam me.’ I think it established him as a threat. You have his independence with Project Vote, you have his refusal to knuckle under during the Alice Palmer thing, and so now you have a series of data points that have some established leaders in the black community feeling disrespected. And so the stage is now set for the comeuppance during the congressional race. That was their payback.”





In the political culture of 1996, two years after the ascendancy of the Gingrich Republicans, many Democrats ran as chastened and cautious politicians; among them was Bill Clinton, who turned his reëlection-campaign strategy over to Dick Morris (who had worked for Jesse Helms and Trent Lott, as well as Democrats) and the militantly centrist pollster Mark Penn (the Morris protégé who helped run Hillary Clinton’s primary campaign). By then, Bill Clinton had abandoned his effort for universal health care and was about to sign into law a welfare-reform bill that Senator Daniel Patrick Moynihan had denounced, saying, “For the first time since it was enacted in 1935, we are about to repeal a core provision of the Social Security Act.” The bill was one of the most important factors in securing Clinton’s reëlection.

Had Obama not been running for office in one of the most liberal districts in Illinois, he would have drawn notice as a fairly bold Democrat. To judge by his public comments, he seemed both appalled and impressed by President Clinton’s political skill. In an interview with the Cleveland Plain Dealer, published a few days after Clinton said that he would sign the welfare-reform bill, Obama talked about the Presidential campaign, saying that Bob Dole “seems to me to be a classic example of somebody who had no reason to run. You’re seventy-three years old, you’re already the third-most-powerful man in the country. So why? . . . And Bill Clinton? Well, his campaign’s fascinating to a student of politics. It’s disturbing to someone who cares about certain issues. But politically it seems to be working.”

Soon, Obama began writing a regular column—“Springfield Report”—for the Hyde Park Herald. In the first one, on February 19, 1997, he wrote, “Last year, President Clinton signed a bill that, for the first time in 60 years, eliminates the federal guarantee of support for poor families and their children.” The column was earnest and wonky. It betrayed no hint of liberal piety about the new law, but emphasized that there weren’t enough entry-level jobs in Chicago to absorb all the welfare recipients who would soon be leaving the system.

In effect, while President Clinton and the national Democratic Party were drifting to the right, State Senator Obama pushed in the opposite direction. The new welfare law was one of the first issues that Obama faced as a legislator. “I am not a defender of the status quo with respect to welfare,” he said, choosing his words with care during debate on the Illinois Senate floor. “Having said that, I probably would not have supported the federal legislation, because I think it had some problems. But I’m a strong believer in making lemonade out of lemons.” Perhaps the law’s most punitive aspect was that it cut off aid to poor legal immigrants, a provision that Clinton, in his 2004 memoir, called “particularly harsh” and “unjustifiable.” The law that Obama helped pass in Illinois restored benefits to this group. (In a continuing effort to produce lemonade, Obama’s first ad of the 2008 general-election campaign says that he “passed laws moving people from welfare to work.”) Obama resisted the national rightward trend of the mid-nineties in other small ways. He sponsored an amendment to the state constitution that would have made health care a universal right in Illinois and helped pass an ethics bill that reformed Illinois’s antiquated campaign-finance system.

In hindsight, little of his legislative record seems controversial. Some of the bills that he sponsored, statements that he made, and votes that he cast could be caricatured in a Presidential campaign. (In one 1997 column, he said, “I supported Governor Edgar’s plan to raise the income tax,” and in a 1999 debate, speaking of himself and his two opponents, he noted that “we’re all on the liberal wing of the Democratic Party.”) But 2008 is not 1988, and Republican attacks on tax hikes and calling an opponent a liberal lack much of their formerly compelling electoral power.

Obama has benefitted from impeccable timing. As the national Party entered a period of ideological timidity, he was at the vanguard of a Democratic revival in Illinois that had begun in 1992, when Clinton and Braun won the state, and grew stronger when, four years later, Democrats took over the Illinois House of Representatives. It continued through 2002, when Democrats won the State Senate and the governor’s office. By 2004, when Obama ran for the United States Senate, Illinois was a solidly blue state.

Not all of this was due to Democratic ingenuity; during this period the state Republican Party collapsed under the weight of corruption scandals. That is something of an Illinois tradition: four of the last nine governors have been indicted on charges of corruption, and three were convicted. As Saul Bellow once remarked, “Politics are politics, crime is crime, but in Chicago they occasionally overlap. The line between virtue and vice meanders madly—effective government on one side, connections on the other.”

There were further changes under way in Chicago. Obama had won his first campaign by using old-fashioned Chicago machine tactics at a time when the notion of machine politics was increasingly anachronistic. As the political consultant Don Rose and his colleague James Andrews explain in a chapter for a book about the current Mayor Daley’s first victory, the machine literally provided voters with access to food, health care, and a job. In most American cities, that model vanished after the Second World War; by then, the blue-collar base was leaving for the suburbs and reform movements were challenging machine politics. In Chicago, Rose and Andrews say, the elder Daley updated and preserved the system by creating a modern machine that combined “big labor and big capital, blue and white collars, and minorities”—a hybrid model that died with him.

Gradually, Chicago caught up with the rest of the country and media-driven politics eclipsed machine-driven politics. “It became increasingly difficult to get into homes and apartments to talk about candidates,” Rose said. “High-rises were tough if not impossible to crack, and other parts of the city had become too dangerous to walk around in for hours at a time. And people didn’t want to answer their doors. Thus the increasing dependence on TV, radio, direct mail, phone-banking, robocalls, et cetera—all things that cost a hell of a lot more money than patronage workers, who were themselves in decline, anyway, because of anti-patronage court rulings.” Instead of a large army of ward heelers dragging people to the polls, candidates needed a small army of donors to pay for commercials. Money replaced bodies as the currency of Chicago politics. This new system became known as “pinstripe patronage,” because the key to winning was not rewarding voters with jobs but rewarding donors with government contracts.

E. J. Dionne, Jr., of the Washington Post, wrote about this transition in a 1999 column after Daley was reëlected. Dionne wrote about a young Barack Obama, who artfully explained how the new pinstripe patronage worked: a politician rewards the law firms, developers, and brokerage houses with contracts, and in return they pay for the new ad campaigns necessary for reëlection. “They do well, and you get a $5 million to $10 million war chest,” Obama told Dionne. It was a classic Obamaism: superficially critical of some unseemly aspect of the political process without necessarily forswearing the practice itself. Obama was learning that one of the greatest skills a politician can possess is candor about the dirty work it takes to get and stay elected.

At the time, Obama was growing closer to Tony Rezko, who eventually turned pinstripe patronage into an extremely lucrative way of life. Rezko’s rise in Illinois was intertwined with Obama’s. Like Abner Mikva and Judson Miner, he had tried to recruit Obama to work for him. Chicago had been at the forefront of an urban policy to lure developers into low-income neighborhoods with tax credits, and Rezko was an early beneficiary of the program. Miner’s law firm was eager to do the legal work on the tax-credit deals, which seemed consistent with the firm’s over-all civil-rights mission. A residual benefit was that the new developers became major donors to aldermen, state senators, and other South Side politicians who represented the poor neighborhoods in which Rezko and others operated. “Our relationship deepened when I started my first political campaign for the State Senate,” Obama said earlier this year, in an interview with Chicago reporters.

Rezko was one of the people Obama consulted when he considered running to replace Palmer, and Rezko eventually raised about ten per cent of Obama’s funds for that first campaign. As a state senator, Obama became an advocate of the tax-credit program. “That’s an example of a smart policy,” he told the Chicago Daily Law Bulletin in 1997. “The developers were thinking in market terms and operating under the rules of the marketplace; but at the same time, we had government supporting and subsidizing those efforts.” Obama and Rezko’s friendship grew stronger. They dined together regularly and even, on at least one occasion, retreated to Rezko’s vacation home, in Lake Geneva, Wisconsin.





Obama’s subtle understanding of the way the city’s politics had changed—with fund-raising replacing organization as the key to victory—surely encouraged him in his next campaign. Almost as soon as he got to Springfield, he was planning another move. He was bored there—once, he appeared to doze off during a caucus meeting—and frustrated by the Republicans’ total control over the legislature. He seemed to believe, according to colleagues at the time, that he was destined for better things than being trapped in one of America’s more notoriously corrupt state capitals. Obama spent little time socializing with “the guys basically from Chicago,” the veteran senator Emil Jones said. “He hung around a lot of the downstaters. They became good friends.”

Obama’s relations with some of his black colleagues from Chicago were dreadful from the beginning. On March 13, 1997, Obama introduced one of his first pieces of legislation, a modest bill to make a directory of community-college graduates available to local employers. There was a response from Rickey Hendon, a state senator from the West Side of Chicago who had been close to Alice Palmer. After Obama explained his bill, Hendon, who has dabbled in film and television work, earning him the nickname Hollywood, rose to ask a question, and the following exchange occurred:

HENDON: Senator, could you correctly pronounce your name for me? I’m having a little trouble with it.
OBAMA: Obama.
HENDON: Is that Irish?
OBAMA: It will be when I run countywide.
HENDON: That was a good joke, but this bill’s still going to die. This directory, would that have those 1-800 sex line numbers in this directory?
OBAMA: I apologize. I wasn’t paying Senator Hendon any attention.
HENDON: Well, clearly, as poorly as this legislation is drafted, you didn’t pay it much attention either. My question was: Are the 1-800 sex line numbers going to be in this directory?
OBAMA: Not—not—basically this idea comes out of the South Side community colleges. I don’t know what you’re doing on the West Side community colleges. But we probably won’t be including that in our directory for the students.
HENDON: . . . Let me just say this, and to the bill: I seem to remember a very lovely Senator by the name of Palmer—much easier to pronounce than Obama—and she always had cookies and nice things to say, and you don’t have anything to give us around your desk. How do you expect to get votes? And—and you don’t even wear nice perfume like Senator Palmer did. . . . I’m missing Senator Palmer because of these weak replacements with these tired bills that makes absolutely no sense. I . . . I definitely urge a No vote. Whatever your name is.

Although the exchange was part of a longstanding tradition of hazing new legislators, the tensions between Hendon and Obama were real. On another occasion, Obama voted—a parliamentary error, Obama says—to block funding for a child-welfare facility in Hendon’s district. Hendon rose and criticized Obama for the vote. The two men became embroiled in a yelling match on the Senate floor that looked as if it might become physical; they were separated by Courtney Nottage, then the chief of staff for Emil Jones. Nottage led Obama off the floor to a room that legislators used to make telephone calls. “It looked like two men that were having a serious disagreement and they had walked up to one another really close,” Nottage told me. “I didn’t think anything good could come of that.”

Hendon told me, “He’s the one that got mad, because he said I embarrassed him on the Senate floor. That’s when he came over to my desk.” Before Nottage broke them up, Obama, who had learned to box from his Indonesian stepfather, supposedly told Hendon, “I’m going to kick your ass!” Hendon said, “He said something like that.” He added that more details will appear in a book that he’s written, entitled “Black Enough, White Enough: The Obama Dilemma.”

Obama’s friends were not surprised when, in 1999, he decided to challenge Bobby Rush, who has represented the South Side in Congress since 1992. Rush had run against Daley in the 1999 mayoral primary, and Obama interpreted Rush’s defeat in that citywide race as a harbinger of his declining popularity in his congressional district.

The race against Rush was the turning point in Obama’s political career. It started with a brilliant bit of oratory that alluded to Abner Mikva’s story about the insularity of Chicago politics and sought to turn Obama’s disadvantages into strengths. “Nobody sent me,” Obama said at his campaign kickoff, on September 26, 1999. “I’m not part of some long-standing political organization. I have no fancy sponsors. I’m not even from Chicago. My name is Obama. Despite that fact, somebody sent me. . . . The men on the corner in Woodlawn drowning their sorrows in alcohol . . . the women working two jobs. . . . They’re all telling me we can’t wait.” It was the best moment of his campaign.

Obama was financially outmatched. Although he raised about six hundred thousand dollars, sustained television advertising in Chicago cost between two hundred thousand and three hundred thousand dollars a week, according to Dan Shomon, Obama’s campaign manager at the time. A series of unusual events defined the race. A few months before the election, Rush’s twenty-nine-year-old son, Huey Rich, was shot and killed, which made the incumbent a figure of sympathy, and in the final weeks of the campaign Rush’s father died. Obama made a serious misstep when, visiting his grandmother in Hawaii, he missed a crucial vote on gun-control legislation in Springfield. Even worse, on the day of the vote a column by Obama about how the gun bill was “sorely needed” appeared in the Hyde Park Herald, under the headline “IDEOLOGUES FRUSTRATE GUN LAW.” Obama protested that his daughter was ill and unable to travel, and that he saw his grandmother, who lived alone, only once a year, but the press treated the trip as a tropical vacation.

Obama lost by thirty-one points—a humiliating defeat. On Election Night, at the Ramada Inn where he had begun his political career, he sounded dejected, hinting that he might leave politics. “I’ve got to make assessments about where we go from here,” he said. “We need a new style of politics to deal with the issues that are important to the people. What’s not clear to me is whether I should do that as an elected official or by influencing government in ways that actually improve people’s lives.” The defeat marked not so much the beginning of a new style of politics for Obama as the beginning of Obama’s mastery of the old style of politics.

Obama had misread the political dynamics of Rush’s unsuccessful mayoral campaign. “He thought he would get some help from Daley because Rush had run against Daley for mayor,” Mikva said. “He thought that Daley might use the opportunity to get even. That’s not the way the Daleys work. It’s not the way the machine works. When Barack went in to see the Mayor, whom he knew slightly, Daley said what his old man used to say: ‘Good luck!’ ”

Mayor Daley concurred. “Bobby Rush was very strong,” he said. “When you lose a race, you can be strong in another avenue, and he was always strong in his congressional district. It was a learning experience when I lost to Harold Washington. The next day, I endorsed him.” He added, “You learn from defeat. If you don’t learn from defeat, then you go away as a sour politician—you think that people turned on you. Barack Obama understood that. The lesson from that campaign is you can’t just run for any office saying you thought someone lost an election and you thought they were weak. He realized that and he rededicated himself.”





Obama learned the exact nature of his appeal, as well as his handicaps. Unlike Obama’s State Senate district, where the University of Chicago and the multicultural Hyde Park produced most of the votes, Rush’s congressional district extended deep into black neighborhoods where Obama was unknown. His academic background was a burden, too. Will Burns explained, “Even though the University of Chicago is one of the largest employers on the South Side of Chicago, it is seen by some, particularly black nationalists, as a bastion of white political power, as a huge entity that doesn’t take into account the interests of the community, that doesn’t have a full democratic partnership with the community, and does what it wants to the community in maintaining clear boundaries about where black people are. It’s seen as an expansive force, trying to expand into Bronzeville and into Woodlawn”—historically black neighborhoods adjacent to Hyde Park—“and put poor blacks out of the area. The University of Chicago is not a brand that helps you if you’re trying to get votes on the South Side of Chicago.”

Obama’s fund-raising success and his professional networks were also viewed with suspicion. Chicago is still a city of villages, and Obama was adept at gliding back and forth between the South Side, where he campaigned for votes, and the wealthy Gold Coast, the lakefront neighborhood of high-rise condominiums and deluxe shopping, where he raised money. One day in Hyde Park, I mentioned the name Bettylu Saltzman (the Project Vote supporter and daughter of a Bulls owner) to Lois Friedberg-Dobry (the South Side operator). “I don’t run in those circles,” she said. Later, over lunch with Saltzman at a café in a gourmet supermarket on the Gold Coast, I mentioned the Dobrys and Obama’s Independent Voters of Illinois friends, and she said, “You know, the North Side and the South Side of Chicago—it’s like two different worlds.”

A South Side operator named Al Kindle, a large man with a booming voice, was a field operator for Obama’s race against Rush. He had helped elect Harold Washington, and he saw Obama’s congressional campaign from the street level. We met one evening at Calypso Café, a Caribbean restaurant that Obama has said is his favorite place to eat in Hyde Park, and Kindle described some of the worst moments in the campaign. “The accusations were that Obama was sent here and owned by the Jews,” Kindle said. “That he was here to steal the black vote and steal black land and that he was represented by the—as they were called—‘the white man.’ And that Obama wasn’t black enough and didn’t know the black experience, the black community. It was quite deafening in terms of how they went after Alderman Preckwinkle and myself. People would say, ‘Oh, Kindle, man, we trust you, you being fooled. Obama’s got you fooled.’ And some people called me a traitor.”

The loss taught Obama a great deal about the components of his natural coalition. According to Dan Shomon, the first poll that Obama conducted revealed that the demographic he could win over most easily was white voters. Obama, who hadn’t shown any particular gift for oratory in the race, now learned to shed his stiff approach to campaigning—described by Preckwinkle as that of an “arrogant academic.” Mikva told me, “The first time I heard him talk to a black church, he was very professorial, more so even than he was in the white community. There was no joking, no self-deprecation, no style. It didn’t go over well at all.”

But, as he had in his 1996 campaign, Obama had attracted a young and zealous corps of campaign workers. “I remember one of the candidates in the race used to talk about how crazed our volunteers were, because they were passionate, energized,” Will Burns said. “You’d come by the office on Eighty-seventh Street and there’d be a bunch of guys with no teeth waiting to get their next Old Grand-dad and then these Shiraz-drinking, Nation-reading, T.N.R.-quoting young black folk. It was a random-ass mix. It was beautiful, though. When I see the crowds now, they’re very reminiscent of what was happening then.”

Emil Jones told me that, after 2000, Obama moved decisively away from being pigeonholed as an inner-city pol. During one debate with Rush, he noted that he and the other candidates were all “progressive, urban Democrats.” Even though he lost, that primary taught him that he might be something more than that. “He learned that for Barack Obama it was not the type of district that he was well suited for,” Jones said. “The type of campaign that he had to run to win that district is not Barack Obama. It was a predominantly African-American district. It was a district where you had to campaign solely on those issues. And Barack did not campaign that way, and so as a result he lost. Which was good.” Meaning, it was good for Barack Obama.

One day in the spring of 2001, about a year after the loss to Rush, Obama walked into the Stratton Office Building, in Springfield, a shabby nineteen-fifties government workspace for state officials next to the regal state capitol. He went upstairs to a room that Democrats in Springfield called “the inner sanctum.” Only about ten Democratic staffers had access; entry required an elaborate ritual—fingerprint scanners and codes punched into a keypad. The room was large, and unremarkable except for an enormous printer and an array of computers with big double monitors. On the screens that spring day were detailed maps of Chicago, and Obama and a Democratic consultant named John Corrigan sat in front of a terminal to draw Obama a new district. Corrigan was the Democrat in charge of drawing all Chicago districts, and he also happened to have volunteered for Obama in the campaign against Rush.

Obama’s former district had been drawn by Republicans after the 1990 census. But, after 2000, Illinois Democrats won the right to redistrict the state. Partisan redistricting remains common in American politics, and, while it outrages a losing party, it has so far survived every legal challenge. In the new century, mapping technology has become so precise and the available demographic data so rich that politicians are able to choose the kinds of voter they want to represent, right down to individual homes. A close look at the post-2000 congressional map of Bobby Rush’s district reveals that it tears through Hyde Park in a curious series of irregular turns. One of those lines bypasses Obama’s address by two blocks. Rush, or someone looking out for his interests, had carved the upstart Obama out of Rush’s congressional district.

In truth, Rush had little to worry about; Obama was already on a different political path. Like every other Democratic legislator who entered the inner sanctum, Obama began working on his “ideal map.” Corrigan remembers two things about the district that he and Obama drew. First, it retained Obama’s Hyde Park base—he had managed to beat Rush in Hyde Park—then swooped upward along the lakefront and toward downtown. By the end of the final redistricting process, his new district bore little resemblance to his old one. Rather than jutting far to the west, like a long thin dagger, into a swath of poor black neighborhoods of bungalow homes, Obama’s map now shot north, encompassing about half of the Loop, whose southern portion was beginning to be transformed by developers like Tony Rezko, and stretched far up Michigan Avenue and into the Gold Coast, covering much of the city’s economic heart, its main retail thoroughfares, and its finest museums, parks, skyscrapers, and lakefront apartment buildings. African-Americans still were a majority, and the map contained some of the poorest sections of Chicago, but Obama’s new district was wealthier, whiter, more Jewish, less blue-collar, and better educated. It also included one of the highest concentrations of Republicans in Chicago.

“It was a radical change,” Corrigan said. The new district was a natural fit for the candidate that Obama was in the process of becoming. “He saw that when we were doing fund-raisers in the Rush campaign his appeal to, quite frankly, young white professionals was dramatic.”

Obama’s personal political concerns were not the only factor driving the process. During the previous round of remapping, in 1991, Republicans had created Chicago districts where African-Americans were the overwhelming majority, packing the greatest number of loyal Democrats into the fewest districts. A decade later, Democrats tried to spread the African-American vote among more districts. The idea was to create enough Democratic-leaning districts so that the Party could take control of the state legislature. That goal was fine with Obama; his new district offered promising, untapped constituencies for him as he considered his next political move. “The exposure he would get to some of the folks that were on boards of the museums and C.E.O.s of some of the companies that he would represent would certainly help him in the long run,” Corrigan said.

In the end, Obama’s North Side fund-raising base and his South Side political base were united in one district. He now represented Hyde Park operators like Lois Friedberg-Dobry as well as Gold Coast doyennes like Bettylu Saltzman, and his old South Side street operative Al Kindle as well as his future consultant David Axelrod. In an article in the Hyde Park Herald about how “partisan” and “undemocratic” Illinois redistricting had become, Obama was asked for his views. As usual, he was candid. “There is a conflict of interest built into the process,” he said. “Incumbents drawing their own maps will inevitably try to advantage themselves.”

The partisan redistricting of Illinois may have been the most important event in Obama’s early political life. It immediately gave him the two things he needed to run for the Senate in 2004: money and power. He needed to have several times as much cash as he’d raised for his losing congressional race in 2000, and many of the state’s top donors now lived or worked in his district. More important, the statewide gerrymandering made it likely that Obama’s party would take over the State Senate in 2002, an event that would provide him with a platform from which to craft a legislative record in time for the campaign.

Obama’s political activity from 2001 to 2004 reveals a man transformed. The loss to Rush drained him of much of the naïveté he once exuded. For instance, when Obama arrived in Springfield, in 1996, he was still enamored of the spirit of community organizing and determined to apply its principles as a legislator. In an interview with the Chicago Reader in 1995, he laid out this vision:

People are hungry for community; they miss it. They are hungry for change. 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. We would come together to form concrete economic development strategies, take advantage of existing laws and structures, and create bridges and bonds within all sectors of the community. We must form grass-root structures that would hold me and other elected officials more accountable for their actions.

Obama took at least one concrete step to turn this notion of the legislator as community organizer into a reality. In his first column in the Hyde Park Herald, the same one in which he addressed welfare, he announced that he was “organizing citizens’ committees” to help him shape legislation. He asked his constituents to call his office if they wanted to participate. That kind of airy talk about changing politics gave way almost immediately to the realities of the job. I asked a longtime Obama friend what ever became of the committees. “They never really got off the ground,” he said. By 2001, if there was any maxim from community organizing that Obama lived by, it was the Realpolitik commandment of Saul Alinsky, the founding practitioner of community organizing, to operate in “the world as it is and not as we would like it to be.”

In electoral politics, operating in the world as it is means raising money. Obama expanded the reach of his fund-raising. Every network that he penetrated brought him access to another. Christie Hefner, Hugh Hefner’s daughter, who runs Playboy Enterprises from the fifteenth floor of a lakefront building, explained how it worked. Hefner is a member of a group called Ladies Who Lunch—nineteen Chicago women, most of them wealthy, who see themselves as talent scouts and angel investors for up-and-coming liberal candidates and activists. They interview prospects over a meal, often in a private dining room at the Arts Club of Chicago. Obama’s friend Bettylu Saltzman, a Ladies Who Lunch member, introduced Obama to the group when he was preparing his Senate run. Hefner, who declined to support Obama in 2000, was ready to help him when he came calling in 2002.

Not long ago, Hefner and I talked in her office; we were seated at a granite table strewn with copies of Playboy. “I was very proud to be able to introduce him during the Senate race to a lot of people who have turned out to be important and valuable to him, not just here but in New York and L.A.,” Hefner explained. She mentioned Thomas Friedman, the Times columnist, and Norman Lear, the television producer. “I try and think about people who I think should know him.”





One insight into the transition that Obama was making during the short period between his painful loss to Bobby Rush and his Senate victory can be gained by comparing his reactions to the two major national-security crises of the time: the terrorist attacks of September 11, 2001, and the Iraq war. For many Illinois state legislators, September 11th was not an event that required much response. The attacks occurred just before an important deadline in the redistricting process. John Corrigan, the Democratic consultant in charge of redistricting, told me that he spent September 12th talking to many legislators, Obama not among them. “It was like nothing had happened,” he said. “Everybody came in and all they cared about was their districts. It wasn’t any one particular legislator from any one particular community. I learned a lot about state government. Their job was not to respond to September 11th. They were more worried about making sure that they had a district that they could run in for reëlection.”

Obama’s response to the event was published on September 19th in the Hyde Park Herald:

Even as I hope for some measure of peace and comfort to the bereaved families, I must also hope that we as a nation draw some measure of wisdom from this tragedy. Certain immediate lessons are clear, and we must act upon those lessons decisively. We need to step up security at our airports. We must reexamine the effectiveness of our intelligence networks. And we must be resolute in identifying the perpetrators of these heinous acts and dismantling their organizations of destruction.
We must also engage, however, in the more difficult task of understanding the sources of such madness. The essence of this tragedy, it seems to me, derives from a fundamental absence of empathy on the part of the attackers: an inability to imagine, or connect with, the humanity and suffering of others. Such a failure of empathy, such numbness to the pain of a child or the desperation of a parent, is not innate; nor, history tells us, is it unique to a particular culture, religion, or ethnicity. It may find expression in a particular brand of violence, and may be channeled by particular demagogues or fanatics. Most often, though, it grows out of a climate of poverty and ignorance, helplessness and despair.
We will have to make sure, despite our rage, that any U.S. military action takes into account the lives of innocent civilians abroad. We will have to be unwavering in opposing bigotry or discrimination directed against neighbors and friends of Middle Eastern descent. Finally, we will have to devote far more attention to the monumental task of raising the hopes and prospects of embittered children across the globe—children not just in the Middle East, but also in Africa, Asia, Latin America, Eastern Europe and within our own shores.

A year later, Obama agreed to speak at an antiwar rally in downtown Chicago, organized by Bettylu Saltzman and some friends, who, over Chinese food, had decided to stage the protest. Saltzman asked John Mearsheimer, a professor of political science at the University of Chicago—and, later, the co-author of the controversial book “The Israel Lobby and U.S. Foreign Policy”—to speak, but he couldn’t make it. “He was one of the main people we wanted, but he was speaking at the University of Wisconsin that day,” Saltzman said. Then she called her rabbi and then Barack Obama. Michelle answered the phone and passed the message on to her husband, who was out of town.

Saltzman also called Marilyn Katz, who runs a Chicago public-relations firm and is close to Mayor Daley. Katz managed to get Jesse Jackson as a speaker, and handled many of the organizing details. Katz, a petite woman who was, improbably, the head of security for S.D.S. at the 1968 Democratic Convention, described what she felt the political mood was at the time of the rally. “Professors are being turned in on college campuses, Bush’s ratings are eighty-seven per cent,” she said. “Among my friends, there hasn’t been an antiwar demonstration in twenty years. There’s huge repression, Bush has got all this legislation. They’re talking about lists, they’re denying people entry into the country. . . . Bush’s numbers were tremendously high, but we had no choice. Unless we wanted to live in a country that was fascist.”

Despite the politics of Saltzman and Katz, Obama’s now famous speech was notable for the absence of the traditional tropes of the antiwar left. In his biography of Obama, David Mendell, noting that Obama’s speech occurred a few months before the official declaration of his U.S. Senate candidacy, suggests that the decision to publicly oppose the war in Iraq was a calculated political move intended to win favor with Saltzman. The suggestion seems dubious; the politics were more in the framing of his opposition, not the decision itself. As Saltzman told me, “He was a Hyde Park state senator. He had to oppose the war!”

The sensitive language of his September 11th statement was gone. Instead, Obama distanced himself from the pacifist activists who were surely present. “Let me begin by saying that although this has been billed as an antiwar rally, I stand before you as someone who is not opposed to war in all circumstances,” he told the crowd. He then went further, defending justifiable wars in almost glorious terms. “The Civil War was one of the bloodiest in history, and yet it was only through the crucible of the sword, the sacrifice of multitudes, that we could begin to perfect this union, and drive the scourge of slavery from our soil. I don’t oppose all wars. My grandfather signed up for a war the day after Pearl Harbor was bombed, fought in Patton’s Army. He saw the dead and dying across the fields of Europe; he heard the stories of fellow-troops who first entered Auschwitz and Treblinka. He fought in the name of a larger freedom, part of that arsenal of democracy that triumphed over evil, and he did not fight in vain. I don’t oppose all wars.” It took some nerve to tweak the crowd in this way. After all, it was unlikely that many of the protesters knew who Obama was, and in a lengthy write-up of the event in the Chicago Tribune the following day he was not mentioned. Yet the speech reads as if it had been written for a much bigger audience.

During this period, Obama also became more of a strategist, someone increasingly comfortable discussing the finer points of polls, message, and fund-raising. According to his friends, Obama does not delegate campaign planning. Marty Nesbitt, his best friend, who became a familiar presence on the campaign trail this spring, flying in to play basketball with Obama on primary days, described the first meeting in which Obama pitched the idea of running for the U.S. Senate to his closest advisers and fund-raisers. This was in 2002, and things seemed to be going his way. The incumbent Republican, Peter Fitzgerald, was unpopular, and the race was attracting a large field of Democrats.

“He didn’t start telling people he was interested in running for Senate until he figured out what the road map was,” Nesbitt said. “He had a good sense of the odds, and he knew there were certain things that had to happen. . . . The first thing he said was, ‘O.K., nobody with approval ratings like this has ever been reëlected, so it’s not gonna be him, right?’ And then he said there’s a bunch of candidates who can potentially run, one of whom was Carol Moseley Braun. And he said, ‘If she runs, I probably don’t have a chance, because there’s gonna be certain loyalty within the African-American community to her, even though she had some mistakes, and I’m probably not gonna get those African-American votes, which I need as my base if I’m gonna win. So if she runs, I don’t run.’

“Then he just laid out an economic analysis. It becomes about money, because he knew that if people knew his story they would view him as a better candidate than anybody else he thought might be in the field. And so he said, ‘Therefore, if you raise five million dollars, I have a fifty-per-cent chance of winning. If you raise seven million dollars, I have a seventy-per-cent chance of winning. If you raise ten million dollars, I guarantee victory.”

That year, he gained his first high-level experience in a statewide campaign when he advised the victorious gubernatorial candidate Rod Blagojevich, another politician with a funny name and a message of reform. Rahm Emanuel, a congressman from Chicago and a friend of Obama’s, told me that he, Obama, David Wilhelm, who was Blagojevich’s campaign co-chair, and another Blagojevich aide were the top strategists of Blagojevich’s victory. He and Obama “participated in a small group that met weekly when Rod was running for governor,” Emanuel said. “We basically laid out the general election, Barack and I and these two.” A spokesman for Blagojevich confirmed Emanuel’s account, although David Wilhelm, who now works for Obama, said that Emanuel had overstated Obama’s role. “There was an advisory council that was inclusive of Rahm and Barack but not limited to them,” Wilhelm said, and he disputed the notion that Obama was “an architect or one of the principal strategists.”

David Axelrod, the preëminent strategist in the state, declined to work for Blagojevich. “He had been my client and I had a very good relationship with him, but I didn’t sign on to the governor’s race,” Axelrod said. “Obviously he won, but I had concerns about it. . . . I was concerned about whether he was ready for that. Not so much for the race but for governing. I was concerned about some of the folks—I was concerned about how the race was being approached.” Axelrod’s unease was warranted. Blagojevich and people close to him have been tied to a seemingly endless series of scandals. The trial of Tony Rezko revealed that Rezko used his influence in the Blagojevich administration to profit from companies seeking business with the state. There is speculation that Blagojevich will be the next governor to be indicted, and the Democratic Speaker of the Illinois House, Michael Madigan, has raised the issue of impeachment.

Part of Obama’s political success is that he has been able to exploit relationships with important yet ethically dubious figures in Illinois while still maintaining his independence. In some ways, this is an Illinois tradition. When the liberal reformer Adlai Stevenson ran for governor, in 1948, one Democratic boss reportedly noted that he would “perfume the ticket.” The earnest Lincoln scholar Paul Simon stood out in the Senate for his moral rectitude and his commitment to good government even as his state wallowed in scandal. “The political bosses knew they had to have what they used to call in business a loss leader—the showcasing,” Don Rose, the Chicago political consultant, said. “The car that you sold for under its value for advertising purposes. While you had at the top of your ticket a shining star, under that it was like turning over a rock.”

Obama has said little about the scandals in his home state. Besides the Rezko and Blagojevich cases, there have been indictments and convictions against the Daley administration concerning hiring and contracting practices. Getting close to the sullied political leadership in Illinois was probably an unavoidable cost of winning the U.S. Senate seat. Emil Jones told me that another of the lessons Obama learned after his 2000 loss was the importance of political sponsorship.

Jones and Obama have had a complicated history. As a community organizer, Obama led a protest against Jones, and in his memoir he unflatteringly describes him as an “old ward heeler.” (“I guess he figured I was part of the establishment,” Jones told me, objecting to the description. “He didn’t know too much about politics and he was very idealistic.”) Years later, Jones backed Palmer over Obama in the State Senate race. But their relationship changed dramatically after 2000. When Obama praised Jones as “my political godfather,” Jones began using the theme music from “The Godfather” as his cell-phone ringtone.

I spoke to Jones in his office minutes after he left a meeting with the Governor, a close ally whom he has defended during the recent difficulties. Jones, who is seventy-two, is a former sewer inspector and insurance salesman; he speaks in a soft rumble and practices politics in a characteristically Chicago manner. He recently explained his support for a proposal to increase the salaries of legislators by saying, “I need a pay raise.” In May, the Chicago Sun-Times reported that Jones “provided himself with tens of thousands of dollars in interest-free loans from his campaign fund,” which, the report noted, is not illegal in Illinois but is “highly unusual.” A spokesman for Jones said that Jones “has always made it a practice to pay back the loans and continues to do so.”

Being in the majority has proved hard for the Democrats. They were having trouble agreeing on a budget deal, and the newspapers were filled with those murmurs of impeachment. For Jones, discussing his long history with the presumptive Democratic Presidential nominee—from target of the youthful Obama’s anti-establishment organizing to political patron in Springfield—seemed a welcome relief, a reminder of happier times for Democrats in Illinois.

“When he ran that race against Bobby Rush, he had no one supporting him who had political influence over others and whom people respected, so he was out there as a lone wolf in that race,” Jones said. That’s why, in 2002, as Obama planned his next campaign, he sought out Jones. “We never discussed it, but he had to analyze that race and recognize he had no other powerful elected officials supporting him,” Jones said. “And so he felt I could be very, very key if he was going to make the run for the U.S. Senate.

“In politics, you must know who is connected to whom,” Jones continued. “The Mayor of Chicago and the father of Dan Hynes”—one of Obama’s primary opponents—“when they were both state senators they shared an apartment together in Springfield, so there’s a relationship between those two. And the Governor? One of his chief financial supporters in his first run was also in the race. I work with both the Mayor and the Governor, so, by my jumping in strong behind Barack Obama, they didn’t want to alienate me and have me upset with them, so they stayed out of the race.”

In the State Senate, Jones did something even more important for Obama. He pushed him forward as the key sponsor of some of the Party’s most important legislation, even though the move did not sit well with some colleagues who had plugged away in the minority on bills that Obama now championed as part of the majority. “Because he had been in the minority, Barack didn’t have a legislative record to run on, and there was a buildup of all these great ideas that the Republicans kept in the rules committee when they were in the majority,” Burns said. “Jones basically gave Obama the space to do what Obama wanted to do. Emil made it clear to people that it would be good for them.” Burns, who at that point was working for Jones, was assigned to keep an eye on Obama’s floor votes, which, because he was a Senate candidate, would be under closer scrutiny. The Obama-Jones alliance worked. In one year, 2003, Obama passed much of the legislation, including bills on racial profiling, death-penalty reform, and expanded health insurance for children, that he highlighted in his Senate campaign.





Perhaps the greatest misconception about Barack Obama is that he is some sort of anti-establishment revolutionary. Rather, every stage of his political career has been marked by an eagerness to accommodate himself to existing institutions rather than tear them down or replace them. When he was a community organizer, he channelled his work through Chicago’s churches, because they were the main bases of power on the South Side. He was an agnostic when he started, and the work led him to become a practicing Christian. At Harvard, he won the presidency of the Law Review by appealing to the conservatives on the selection panel. In Springfield, rather than challenge the Old Guard Democratic leaders, Obama built a mutually beneficial relationship with them. “You have the power to make a United States senator,” he told Emil Jones in 2003. In his downtime, he played poker with lobbyists and Republican lawmakers. In Washington, he has been a cautious senator and, when he arrived, made a point of not defining himself as an opponent of the Iraq war.

Like many politicians, Obama is paradoxical. He is by nature an incrementalist, yet he has laid out an ambitious first-term agenda (energy independence, universal health care, withdrawal from Iraq). He campaigns on reforming a broken political process, yet he has always played politics by the rules as they exist, not as he would like them to exist. He runs as an outsider, but he has succeeded by mastering the inside game. He is ideologically a man of the left, but at times he has been genuinely deferential to core philosophical insights of the right.

Obama’s establishment inclinations have alienated some old friends. During the 2004 Senate primary, Obama sometimes reminded voters of his anti-machine credentials, but at the same time he shrewdly wrote to Mayor Daley’s brother, William, who had backed one of Obama’s primary opponents, asking for his support if he won the primary. As he outgrew the provincial politics of Hyde Park, he became closer to the Mayor, and this accommodation, as well as his unwillingness to condemn the corruption scandals ensnaring Daley and Blagojevich, both of whom he supported for reëlection, have some of his original supporters feeling alienated and angry. “I am not thrilled with Barack, simply because we elected him as an Independent, and he switched over to Daley,” Alan Dobry said. Ivory Mitchell, speaking of Obama’s Senate race, said, “When he won the primary out here and he went downtown, it appears as though Daley took over the campaign for him. . . . We were excluded.” David Axelrod told me, in response, that some of the Independents on the South Side blame Daley for just about anything. “I think there’s kind of this Wizard of Oz mystique,” he said. “Daley had virtually no role in the Senate campaign.”

Another transition from primary to general election is now under way for Obama, and it is causing him a similar set of problems, all of which stem from a realization among his supporters that superheroes don’t become President; politicians do. Judging by the reaction to Obama’s most recent decisions—his willingness to support legislation to modify the Foreign Intelligence Surveillance Act, his rightward shift on interpreting the Second Amendment, his decision to “refine” his Iraq policies—some voters will be crushed by this realization and others will be relieved. In another episode that has Obama’s old friends feeling frustrated, Obama recently blamed his first campaign manager, Carol Anne Harwell, for reporting on a 1996 questionnaire that Obama favored a ban on handguns. According to her friends, Harwell was furious that the campaign made her Obama’s scapegoat. “She got, as the saying goes, run over by a bus,” Lois Friedberg-Dobry said.

Obama’s rise has often appeared effortless. His offstage tactics—when he is engaged in the sometimes combative work of a politician—are rarely glimpsed by outsiders. Penny Pritzker, a friend and fund-raiser for Obama, remembers meeting with him at her office in 2006 to discuss his Presidential campaign. Pritzker, whose family, one of the wealthiest in Chicago, owns the Hyatt hotel chain, was as crucial to Obama’s next campaign as Toni Preckwinkle’s was to his first. “We were talking about whether he was ready to do this or not,” Pritzker told me. She was blunt, telling Obama, “As I see it, the two things that you’re going to need to address are your executive leadership skills, because your résumé doesn’t have that in it, and the second would be your credentials in national security.” Obama returned with an organizational chart indicating how the campaign would be structured—one of his great tactical advantages over the disorganized Clinton campaign—along with a list of advisers. Pritzker agreed to become his finance chair. Obama has frequently been one step ahead of his friends and the public in anticipating his own rise. Perhaps it is all those people he has met over the years who told him that he would be President one day. The Reverend Alvin Love, a South Side Baptist minister and a longtime Obama friend, said that Obama called him in December, 2006, seeking advice about whether to run for President. “My dad told me that you’ve got to strike while the iron is hot,” Love recalls saying, and Obama replied, “The iron can’t get any hotter.”

Obama has always had a healthy understanding of the reaction he elicits in others, and he learned to use it to his advantage a very long time ago. Marty Nesbitt remembers Obama’s utter calm the day he gave his celebrated speech at the 2004 Democratic National Convention, in Boston, which made him an international celebrity and a potential 2008 Presidential candidate. “We were walking down the street late in the afternoon,” Nesbitt told me. “And this crowd was building behind us, like it was Tiger Woods at the Masters.”

“Barack, man, you’re like a rock star,” Nesbitt said.

“Yeah, if you think it’s bad today, wait until tomorrow,” Obama replied.

“What do you mean?”

“My speech,” Obama said, “is pretty good.”