CHICAGO—It started as a crossroads for traders, settlers, and soldiers on the blustery shores of Lake Michigan in the 1830s. Later, it became a prosperous railroad hub and a national center for manufacturing and commerce. It has been the scene of mayhem over the years, like the Great Fire of 1871, the Haymarket labor riot of 1886, and the violent protests at the Democratic National Convention of 1968. And in its brash and boisterous way, Chicago has produced all manner of distinctive leaders, celebrities, and rascals, ranging from liberal lawyer Clarence Darrow to gangster Al Capone, political boss Richard Daley, civil rights leader Jesse Jackson, Nation of Islam Minister Louis Farrakhan, talk-show host Oprah Winfrey, and basketball superstar Michael Jordan.
Now Barack Obama can be added to the list. And as Americans take the measure of the former community organizer on the South Side, few better insights are available into his character, views, and approach to politics than his two decades in Chicago. That's where he developed his commitment to accommodation and honed his ability to navigate smoothly among competing and often angry constituencies, all in a vast human stew of diversity.
"Politics in Chicago is an all-season sport, and it's not for the fainthearted," says U.S. Rep. Rahm Emanuel of the North Side, former White House political director for President Bill Clinton. Adds David Axelrod, a Chicago-based political consultant who is now chief strategist for Obama's presidential campaign: "Ours is a blunt, brawling way. People are upfront about their self-interest." The Chicago style of politics reminds Axelrod of the "invisible man" educational toy he knew as a youth—a human figure whose internal organs were fully exposed. "It's like Chicago—all laid bare," says Axelrod.
Extraordinary skills. In some ways, the narrative of Obama's political career has been oversimplified and distorted, partly because his Chicago background hasn't been sufficiently examined. He is neither an unblemished hero living under a star with only the purest of motives, as many of his supporters hope, nor a weak-minded naif who lacks the toughness to take on his harshest adversaries, as many of his detractors fear. Beyond the hype and the spin, Obama has operated as a conventional politician who has demonstrated some very unusual traits—extraordinary communication skills, the ability to grow as a leader, and the good sense and savvy to recognize a zeitgeist, the nation's powerful desire for change, when he sees one.
He has also exhibited intense personal ambition. In fact, local leaders and Obama friends say he couldn't have succeeded in Chicago without being an idealist, a pragmatist, and to some degree a self-promoter, all at the same time. "It's a great place to learn about politics and what motivates people," says Axelrod.
Unbridled ambition. Obama's Chicago background has enabled him to appeal to many divergent groups, from poor African-Americans to white businessmen, working-class folks, middle-class professionals, wheeler-dealers, mainstream reporters, teachers, suburban parents, professors, and college students. "I'm not surprised he has the skills to appeal to these different constituencies. That's what he learned in Chicago," says a Republican strategist with admiration. Jerry Kellman, who hired him as a community organizer 20 years ago, agrees. "I don't think he would have ended up where he is if he hadn't come to Chicago," says Kellman. "It's where he got an incredible education in real politics. His idealism became tempered with realism and practicality very quickly."
During his two decades of community and political involvement, he climbed the ladder of political success, with only one notable setback, often by adjusting his views and his methods to the needs of the moment. In the process, he learned to play hardball as practiced by local leaders and mentors such as former Mayors Harold Washington and Daley; activists such as Axelrod and Emanuel; religious leaders such as the Rev. Jeremiah Wright, his controversial former pastor; and local wheeler-dealers such as Tony Rezko, who raised money for his political career and helped him acquire property in a controversial land deal.
"Barack is a very egotistical guy with undeniable ambition," says a former adviser who has had a falling-out with him. "When he went national, he didn't care about anything else."
He had no personal connections to Chicago when, at 23 and living in New York after graduating from Columbia, he answered an ad in a trade publication for a community organizer in the Windy City. He was hired, and in June 1985 he moved there in his run-down blue Honda. The job paid a paltry $13,000 a year. He found himself in one of the most fascinating, complicated, and challenging urban environments in the country, a place where, as author David Mendell says, politics, race, and power are "inextricably intertwined."
Kellman, his boss and still a close friend, assigned the earnest newcomer to the Roseland and West Pullman areas on the South Side. The nearly all-black territory included both stable middle-class areas with carefully tended lawns and sections of abject poverty where drug dealers prowled the streets. Obama's assignment was to teach the poor to rely on themselves in a very aggressive way—to get what they wanted from city hall, their landlords, and others in power by clarifying their needs and banding together to take action. It's the kind of self-help that he preaches today as a presidential candidate. And it's the kind of grass-roots activism that he has put to good use in his campaign, which has dominated the presidential caucuses where success is based on the type of person-to-person organizing that he learned in the Windy City.
One of his projects was organizing Altgeld Gardens, a dilapidated housing project with 2,000 residents just outside Roseland, to prod the Chicago Housing Authority to make basic repairs in the apartments, such as fixing toilets and furnaces. He enjoyed only mild success because city authorities were so resistant to change. He also assisted in organizing a campaign to have asbestos removed from the apartments. The housing authority, under pressure from demonstrations that Obama aided in organizing and media attention that he helped to arrange, eventually agreed to test for asbestos and hire workers to seal it off. But in the end, the asbestos removal stalled, and the episode left Obama disappointed in the limits of community organizing without at the same time having allies in power.
Obama also saw firsthand the central role that African-American churches played in the black community, providing solace, pride, and the motivation to persevere against adversity. He got to know Wright, the bombastic and charismatic pastor of Trinity United Church of Christ—whose angry sermons, widely perceived as anti-American and antiwhite, got Obama's presidential campaign into deep trouble a few weeks ago.
Political base. But there was personal motivation, too. Despite having little previous interest in religion, Obama joined Wright's growing church in part to deepen what one friend called "a whole web of relationships" in the community that gave him a strong political base and a well-connected mentor. At one point, Wright warned Obama that the ministers and other leaders in Chicago could be parochial and cynical, which would make Obama's job of organizing much harder. Obama soon learned this in a very personal way when one minister derided him at a public meeting for being a pawn of Chicago's whites because he tried to work with the Establishment.
Wright, who retired earlier this year, belonged to a gospel-shouting tradition in many black churches of "signifying"—connecting with parishioners by linking religion to contemporary life and politics. He was dramatic and topical in part to attract young people to his version of the Christian tradition rather than Islam, which also had appeal to young blacks, to some degree because of charismatic leaders such as Farrakhan. Obama says he recognizes all this, and while he has condemned what Wright said, he refused to "disown" him and his good works in the community. This is seen by Obama confidants as an example of the loyalty so prized in Chicago politics. "He feels that we need to accept people with their imperfections," says a friend. "You don't disown them. It's very much a part of his message." Adds Rep. Jan Schakowsky of Chicago, a supporter: "Barack will not demonize. He won't throw somebody under the bus."
In addition to learning the importance of loyalty in developing his leadership skills, his belief in the importance of charisma grew. After reading Taylor Branch's Parting the Waters, a history of the civil rights era, Obama told a coworker that he wished he had been able to participate in "the movement," but he was "10 years too late." He was uncomfortable with the confrontational style of some civil rights leaders but was inspired by the leadership of Martin Luther King Jr. He concluded that he could make a bigger impact if he got into politics and took on a wider leadership role, combining his own ability to inspire with his commitment to community activism. He enrolled at Harvard Law School and was elected the first African-American president of the Harvard Law Review, a prestigious post reserved for the most talented students.
Neighborhood roots. In the summer of 1988, Obama worked as an intern in the Chicago office of the influential law firm of Sidley Austin. He began dating Michelle Robinson, a young lawyer from a working-class family in the South Shore area of the South Side, who was his mentor at the firm. After they married in 1990, they settled in the Hyde Park neighborhood on the South Side along the lakefront. Anchored by the University of Chicago, the community is populated by both blacks and whites and includes many affluent families of both races, along with the middle class and the poor. It has a strong base of independent voters and a commitment to political reform, all of which have become part of Obama's message today.
After working briefly on a voter registration and education project that helped elect Bill Clinton as president and Carol Moseley Braun as the state's first African-American female senator in 1992, he went to work for Miner, Barnhill & Galland, specializing in civil rights law and other forms of public advocacy. These experiences gave him many contacts in the power structure. But his longtime interest in a political career was inspired mostly by the changes being made in Chicago by Harold Washington, its black mayor. African-Americans were finally getting a share of power they hadn't had before, and Obama again saw how a charismatic political leader could make a real difference.
In 1996 at age 34, he ran for the state Senate in a messy drama that is little known outside of Chicago. Alice Palmer, the incumbent, planned to run for Congress and supported Obama as her successor. But after Palmer's congressional campaign hit some trouble, she decided to run for re-election to the Illinois Senate after all. Obama refused to step aside and found himself in a battle for survival. One of his volunteers challenged the legality of Palmer's nominating petitions, as well as the petitions of other candidates; Palmer dropped out, and the other candidates were disqualified. Obama won unopposed in the Democratic primary—guaranteeing victory in the general election. "The whole episode showed that Obama was an extraordinarily ambitious young man willing to do whatever it took to advance not only his agenda of community empowerment but his own political career," wrote Mendell in Obama: From Promise to Power. Adds a current adviser: "Some say it was coldhearted, but it shows that if he has to pull the trigger, he will."
Building relationships. His South Side district was economically diverse, including some of the poorest black areas and public housing projects but also many areas with mixed-race families and middle- and upper-middle-class households. From the start of his elective career, he preached accommodation and said that his constituents were "hungry for change"—an echo of the theme that has been the centerpiece of his presidential campaign.
He worked with like-minded whites and preferred to operate within the power structure rather than practice the confrontational politics favored by activists of all stripes in Chicago.
Seeking to cultivate as many relationships as he could, Obama took up golf, because so much business was conducted on the fairways. He established close connections with key legislators in Springfield, the state capital. He joined a weekly poker game with other senators. He showed his potential when the Senate overwhelmingly passed a controversial law he sponsored on campaign finance reform in May 1998, prohibiting legislators from raising campaign funds on state property and from accepting gifts from lobbyists and state contractors.
Overall, he built a respectable record, working with both Democrats and Republicans to win approval for a series of bills. They included legislation that compensated crime victims for property losses, prevented early probation for felons who committed crimes with guns, increased penalties for offenders who used date-rape drugs on their victims, established a state-funded screening program for prostate cancer, and increased spending on after-school programs. John Bouman, a director of the National Center on Poverty Law in Chicago, summed up the prevailing assessment of Obama: "idealistic but practical."
In 2000, Obama's ambition led him to run for Congress from Chicago in an ill-fated primary challenge to Democratic Rep. Bobby Rush, 53-year-old former head of the Illinois Black Panther party. The party's slogan was "Power to the People," and one of its projects was arming black men to defend their communities from the white-controlled police. Obama, 38, could never compete with Rush's compelling biography or charisma, and he couldn't overcome doubts that he was authentically connected to the black community.
To make matters worse for Obama, when Rush's son, Huey Rich, was shot to death on a South Side street in October 1999, public sympathy for him grew exponentially. That Christmas, Obama and his family visited his grandmother in Honolulu, and he didn't return to Springfield to vote on a hotly contested gun control bill that lost by three votes, for which he was pilloried in the media. He also did poorly in a key televised debate. State Sen. Donne Trotter, an Obama adversary from Chicago, told the Chicago Reader newspaper in March 2000: "Barack is viewed in part to be the white man in blackface in our community. You just have to look at his supporters. Who pushed him to get where he is so fast? It's these individuals in Hyde Park, who don't always have the best interests of the community in mind." Obama lost to Rush by 30 percentage points.
But he would recover. "You saw his resilience after he lost to Bobby Rush," says Valerie Jarrett, a former senior city official who is now a close Obama adviser. "He has the intestinal fortitude to take a punch—and losing to Congressman Rush was a very hard punch."
But he continued to work actively in the community and look for another way up the ladder. He saw his chance in 2004 when a Republican-held seat in the U.S. Senate opened up. He took a risk and won, putting his Chicago education to good use and promoting the themes of conciliation, multiculturalism, and compromise.
Three years later, he was running for president.