For Obama Chicago Days Honed Tactics

CHICAGO -- In his first run for public office in 1996, Barack Obama faced an unexpected obstacle. A liberal black incumbent had encouraged him to run for the Illinois state senate seat she intended to vacate. Then she changed her mind, deciding to run again.

Mr. Obama hired a fellow Harvard Law School graduate, challenged the validity of signatures on her nominating petitions, and got her thrown off the ballot. He eventually ran unopposed, launching the career that has made him the front-runner for the Democratic nomination for president.

In his books and speeches, Mr. Obama has cast himself as an underdog and an unconventional politician -- a stance that has spawned criticism in advance of Tuesday's Pennsylvania primary that he lacks the political skill and stamina to get elected. A look at his years in Chicago, based on interviews with friends, advisers, rivals and political strategists, reveals a shrewd combatant from one of the nation's toughest political arenas.

After he was criticized as arrogant by some fellow Illinois state legislators, he forged alliances with establishment Republicans and Democrats in meetings and at poker games. After he was trounced in a congressional race by a former Black Panther, he barnstormed black churches to build support for a Senate run. His subsequent victory was helped along by newspaper disclosures of embarrassing material from the divorce papers of a Democratic opponent.

It was during his Chicago years, too, that Mr. Obama struck up friendships with a pastor and a real-estate developer that have since opened him to criticism. And back then, during his only losing campaign, he first faced the kind of criticism that has resurfaced in Pennsylvania: that he is an elitist who is out of touch with the working class and the poor.

Sen. Hillary Clinton, of course, has also come under political attack and has developed a reputation for toughness. In last week's debate in Philadelphia, she said she was "better able and better prepared" to defeat Sen. John McCain "in large measure because of what I've been through."

For many decades, Chicago has been one of the nation's most distinctive political landscapes. Under the longtime leadership of Mayor Richard J. Daley, it became synonymous with one-party rule. Loyal Democrats were rewarded with jobs and services. Neighborhoods seen as politically disloyal sometimes faced problems such as unplowed winter streets. Many blacks felt shut out of the system altogether.

When Mr. Obama arrived in 1985 at the age of 23, the city's political and racial landscape was changing. The city of Mayor Daley and his predominantly white Democratic machine was becoming the city of Michael Jordan and Oprah Winfrey. Harold Washington became the first black mayor in 1983 by reaching out to white voters. When Mayor Daley's son, Richard M. Daley, was elected mayor in 1989, he appointed numerous blacks to high positions, including Mr. Obama's girlfriend and future wife, Michelle.

"Chicago was his Harvard of politics," says Don Rose, a longtime political strategist here. "Had he gone to Cleveland or New York or Atlanta, it might have been a different path."

Mr. Obama declined to be interviewed for this article. But he often points to his Chicago roots as proof that he can take the "sharp elbows" of politics. "I'm from Chicago. I know politics," he said at an outdoor rally in Harrisburg, Pa., on Saturday night. "I'm skinny, but I'm tough."

When Mr. Obama arrived in Chicago a year after graduating from Columbia University, community organizer Gerald Kellman hired him to work in a poor and working-class black neighborhood. He was "very na ve politically," says Mr. Kellman. "He was looking for the civil-rights movement, but the civil-rights movement was over. He was trying to figure out what the equivalent would be."

Life as an Outsider

Mr. Obama had lived much of his life as an outsider: a biracial boy raised by a white mother and grandparents, an American in Indonesia, a Hawaiian native in New York. "He had never encountered blue-collar and lower-class African-Americans," says Mr. Kellman. "If he couldn't be comfortable emotionally with them, he couldn't build a political career."

Mr. Obama organized poor and working-class blacks to lobby for a jobs center and for the removal of asbestos in a local housing project. "He was so young, but we followed him," says Margaret Mabry, who worked with him.

He also worked with white foundation officials to secure grants and support. He lived in Hyde Park, an integrated neighborhood that is home to the University of Chicago, and dated and lived with a woman who wasn't African-American, according to Mr. Kellman. They broke up when he went east to law school.

"He found a way to be part of the black community and live beyond the black community," says Mr. Kellman. "He discovered he could live in both worlds."

While attending Harvard Law School, Mr. Obama decided on a Chicago political career. Returning to the city for a summer law-firm internship, he met his future wife, Michelle. She had grown up in a black neighborhood on the South Side. Her father had been a precinct captain for the first Mayor Daley's political machine, and she knew the families of many black politicians, including Jesse Jackson's.

When Mr. Obama moved back to Chicago in 1991, he settled in Hyde Park, which had a college-town ambience and a history of liberal political activism. The late Mayor Washington had lived in Hyde Park; so did Carol Moseley Braun, elected in 1992 as the first black woman U.S. senator.

Many Chicago law firms courted Mr. Obama. He joined a boutique firm specializing in housing and civil rights. Judson Miner, who had been a close ally of Mayor Washington, headed the firm. Ms. Moseley Braun had worked there before her Senate run.

Mr. Miner is Jewish, like many of the whites in Mr. Obama's network of mentors and donors: Newton Minow, head of the Federal Communications Commission under President Kennedy and a prominent Chicago lawyer; Abner Mikva, a former Chicago congressman and a federal judge; political fund-raisers Betty Lu Saltzman, daughter of wealthy developer Philip Klutznik, and Penny Pritzker, heir to the Hyatt Hotel fortune; and, most importantly, political strategist David Axelrod, who now runs Mr. Obama's presidential campaign.

"I used to tease Barack that he had Jewish blood," says Mr. Miner. The connections to Judaism run even closer to home: Michelle Obama's second cousin converted to Judaism, was ordained a rabbi, and runs a Chicago congregation made up largely of black converts to Judaism.

This year, Jews generally have favored Sen. Clinton. Some cite Mr. Obama's stance on Israel, which they say is insufficiently supportive; others have been troubled by sermons critical of Israel delivered by Rev. Jeremiah Wright, who until recently served as pastor of Mr. Obama's church.

His membership in Trinity Church, the city's largest black church, put him in touch with middle-class and upper-middle-class black professionals, many of them politically active. In the fall of 1995, Mr. Obama attended the "Million Man March" in Washington, organized by Nation of Islam leader Louis Farrakhan. The march, Mr. Obama said in a newspaper interview at the time, was a "powerful demonstration of an impulse and need for African-American men to come together." But he warned in that interview that "cursing out white folks is not going to get the job done. Anti-Semitic and anti-Asian statements are not going to lift us up."

When he entered the race for state senate, he drew from his diverse networks. Mr. Minow invited wealthy Democratic contributors to a fund-raiser at his home. Andrew Rosenfield, a conservative colleague at the University of Chicago Law School, where Mr. Obama was teaching, held a fund-raiser in the overwhelmingly white Republican suburb of Lake Forest. John Rogers, the African-American head of Ariel Capital Management, who was finance chairman for Ms. Moseley Braun's Senate run and friends with Michelle Obama's brother, gave Mr. Obama entree to his extensive network of black and white donors.

'Hungry for Change'

Mr. Obama sounded many of the themes he uses now. "The political debate is now so skewed, so limited, so distorted," he told a Chicago newspaper. "People are hungry for community; they miss it. They are hungry for change."

In the Illinois State Senate, some Democrats and Republicans tagged Mr. Obama as an elitist who looked upon the state legislature as a political stepping stone. Chicagoans who knew him frequently offer stories of his intimidating intellect and sometimes chilly manner -- a counterpoint to the widely circulated stories about his skills as a listener and his ability to connect with people of different views.

"The first time I was on a committee with him, he began asking the witnesses four million questions. I leaned over and said, 'You know, Barack, do me a favor and learn on your own damn time and leave my time free,'" says Denny Jacob, a conservative Democrat who later became a friend and supporter of Mr. Obama's.

"Barack was one of the smartest people I ever worked with, but he was more interested in moving up," says Republican Steven Rauschenberger, who served with Mr. Obama in the state senate. "I never thought he was very engaged in the state senate, because he didn't think that much of it."

A spokesman for the Obama presidential campaign says that he worked with Democrats and Republicans to pass numerous important bills. David Mendell, a Chicago Tribune reporter who covered Mr. Obama and wrote a biography of him, says Mr. Obama "accrued a rather impressive record for a first-term legislator." He shepherded a bipartisan bill that prohibited lawmakers from soliciting campaign funds on state property and accepting gifts from state contractors and lobbyists. After his first term, he forged a close relationship with the new state senate president Emil Jones and helped pass a number of high-profile bills, including legislation to require police to videotape interrogations in murder cases and to curb racial profiling in traffic stops.

But Mr. Obama was aiming for higher things. Against the counsel of many of his advisers, he decided to run in the primary against Democratic Congressman Bobby Rush, a popular former Black Panther who represented a largely black district that included Hyde Park. Mr. Obama lost by 30 percentage points.

"It felt like he was definitely a rising star, but still pretty green," says Eric Adelstein, a Chicago Democratic political consultant who helped run Mr. Rush's campaign. In the largely poor district, Mr. Obama was seen as more of an outsider -- "the Black Panther against the law professor," says Mr. Adelstein.

Learning From Defeat

Mr. Obama next set his sights on the 2004 Senate race. Several white Democrats were planning to run. If Mr. Obama could win the black vote and attract liberal whites, he figured he could get 30% of the vote, enough to win in a crowded field, according to his aides on that campaign. Learning from his prior defeat, he visited three black churches every Sunday, delivering his stump speech in the cadence of black preachers. He raised money furiously.

Most importantly, Mr. Obama persuaded Mr. Axelrod, one of Chicago's most powerful political strategists, to run his campaign. Mr. Axelrod specialized in electing black candidates who could cross over and win white votes, emphasizing themes of unity and change. He also worked for Mayor Daley.

Mr. Obama was running third, behind two white candidates. Throughout the campaign, rumors swirled that Blair Hull, the Democratic front-runner, was involved in a messy divorce. The Chicago Tribune filed a lawsuit seeking to unseal Mr. Hull's divorce papers. Under pressure, Mr. Hull released the papers, which revealed that his ex-wife had alleged that he had physically and verbally abused her. No charges were ever filed, and Mr. Hull said at the time that voters should look at "my total reputation in my life." A spokesman for the Obama presidential campaign says that his senate campaign "was not responsible for the release of the records."

Mr. Axelrod, who had been holding money back, unleashed a flurry of Obama television ads. They made no mention of the Hull matter, but focused on Mr. Obama's biography. Mr. Obama won the primary with 53% of the vote.

Mr. Obama's Republican opponent, Jack Ryan, then withdrew after his divorce papers revealed that his ex-wife had made an allegation connected to what she said were trips she took with Mr. Ryan to sex clubs. Mr. Ryan denied the allegation.

Mr. Obama sailed to victory. By the end of the campaign, his aides were sending workers into Iowa, the first Presidential caucus state, to begin developing contacts among Democrats there, according to Al Kindle, an Obama campaign aid at the time.

A few months later, Sen. Obama entered into a real-estate deal that would later come to haunt him. He and his wife bought a mansion in Hyde Park for $1.65 million, $300,000 below the asking price. The wife of a longtime friend and donor, real-estate developer Tony Rezko, paid full price for an adjacent lot that was listed at the same time by the seller. Six months later, the Rezkos sold Mr. Obama a strip of their land so he could have a bigger yard. At the time, newspapers were reporting that Mr. Rezko was under investigation for corruption and influence peddling involving the Illinois governor's office. He was subsequently indicted and is currently standing trial.

Sen. Obama, who hasn't been named in connection with that case, has since called his decision "boneheaded" because it gave the impression Mr. Rezko was trying to curry favor. Mr. Axelrod says Sen. Obama never discussed the house purchase with his political team. If he had, Mr. Axelrod says, they would have told him not to do it.

Write to Jonathan Kaufman at jonathan.kaufman@wsj.com

Corrections Amplifications

Eric Adelstein is a Chicago Democratic political consultant who helped to run a primary campaign for Rep. Bobby Rush. A previous version of this page-one article about Sen. Barack Obama's experience in Chicago politics, Mr. Adelstein's first name was incorrectly given as David.

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