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."