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.”

“Who Sent You?”

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.”

Constructing A Network

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.”