For Obama, a Handsome Payoff in Political Gambles
Presidential Hopeful Has Friends, Successes and Precious Few Battle Scars

By Peter Slevin
Washington Post Staff Writer
Tuesday, November 13, 2007

CHICAGO -- Those who know Sen. Barack Obama best swear that this is nothing new: Trailing a powerful name in politics, hurrying to build an organization from scratch, struggling to overcome skepticism that he will ever catch up.

"You know what? The same thing in the U.S. Senate race," Michelle Obama said of her husband in a recent interview. "The exact same scenario. This is Barack's political career."

She was referring to Obama's successful 2004 campaign in Illinois, an example of a come-from-behind victory that many Obama advisers like to cite as a model for catching Sen. Hillary Rodham Clinton (N.Y.) and winning the Democratic presidential nomination. Their message: He has been through tough races before.

Yet one of the singular aspects of Obama's rapid political rise is that he accomplished it without becoming controversial, without being bloodied -- indeed, with hardly a scratch, even in rough-and-tumble Chicago, one of America's most famously political cities. He cut a path largely independent of the Democratic machine, its ward bosses and its byzantine rules of succession. Apart from one disastrous decision to run for Congress, he advanced with strong campaigns and some fortuitous implosions by his rivals.

Bill Daley, the politically minded son and brother of Chicago's longest-serving mayors, is a former member of President Bill Clinton's Cabinet who defected and became a valuable Obama adviser. He likes Obama because he is "hometown" and "the ultimate change guy -- the look, how he came up in politics, everything."

But, he added: "I would not say he comes from Chicago politics."

Now, as Obama finds himself in an increasingly contentious race for the Democratic nomination, he faces choices that are relatively new for him. He must draw ever sharper distinctions with his opponents, particularly Clinton, without violating his own professed stand against focusing on the negative.

"I want to campaign the same way I govern, which is to respond directly and forcefully with the truth," Obama told The Post last week. "That means I'm not going to paint a caricature of Senator Clinton. I think she's a smart, able person. I think anybody who tries to paint her as all negative is engaging in caricature, and when you start slipping into that mode, it's hard to come back."

Obama watchers in Chicago say that waging a battle for the White House against Clinton and the rest of a national field is far different from anything he faced at home.

"Hillary's team is the most experienced and most successful Democratic operation in 30 years," said a well-connected Chicago political consultant. "What Barack has shown is the ability to raise a prodigious amount of money. The one thing I don't know that Barack has proven is, can he take a punch? Can he take a sustained attack?"

As Obama rose from being a $1,000-a-month community organizer on Chicago's South Side to become a U.S. senator by 43, he made few headline-making mistakes and few enemies. He was never a target of serious scrutiny, unlike Clinton and Republican front-runner Rudolph W. Giuliani, whose career in New York unfolded under the relentless gaze of the media. "He almost universally avoided personal attacks," said Dan Shomon, a former Obama campaign manager. "He's really a policy wonk at heart."

"Mentally, physically, he is ready. He's ready to be attacked on his policies," Shomon said. "If there are personal attacks against him or his family, I don't know how he will handle that, because he has not been through that."

In Obama's first successful campaign, he was not the candidate.

It was 1992 and he had recently finished Harvard Law School and returned to Chicago, spurning prestigious law jobs to work closer to the ground. He went to work for Project Vote, a voter registration drive that boosted the candidacy of Carol Moseley Braun (D), only the second black U.S. senator since Reconstruction. Sandy Newman, who recruited Obama, said he offered him the job with limited expectations. Fundraising was not in the job description, yet Obama "raised more money than any of our state directors had ever done. He did a great job of enlisting a broad spectrum of organizations and people, including many who did not get along well with one another."

Obama recruited a fundraising committee chaired by John Schmidt, a white former chief of staff to Mayor Richard M. Daley (D) and John W. Rogers Jr., a young black money manager and founder of Ariel Capital Management. In less than a year, Obama hired 10 workers, attracted 700 volunteers and produced 150,000 new voters.

By the end, Schmidt was struck by the fact that the drive actually registered voters.

"He really did it, and he let other people take all the credit. The people standing up at the press conferences were Jesse Jackson and Bobby Rush and I don't know who else. Barack was off to the side and only the people who were close to it knew he had done all the work."

Three years later, Obama ran for office himself. He used his elbows.

At the time, he was teaching constitutional law at the University of Chicago and working at a small civil rights firm after finishing his memoir "Dreams From My Father: A Story of Race and Inheritance." He spotted an opportunity when Alice Palmer, a progressive black state senator, ran for Congress in an off-year election.

Palmer assured Obama that she was comfortable surrendering her safe seat in a community that had produced a string of successful anti-machine candidates, including the late Sen. Paul Douglas (D) and Abner Mikva, future member of Congress, federal judge and White House counsel. She informally blessed his candidacy and said if she lost the House race, she would not drop back into the Illinois contest.

But after Jesse Jackson Jr. (D) won the special election in November 1995, Palmer had second thoughts. Her followers pressed Obama to drop out. He refused. Palmer and her supporters hurriedly gathered hundreds of signatures to put her name on the ballot.

Obama challenged the validity of some of the signatures on the petitions before the Chicago Board of Election Commissioners. He also contested the petitions submitted by his three other Democratic opponents. The authorities ruled all four opponents ineligible, clearing the field.

"It took some real guts to do it," Schmidt said. "There were a lot of people who said, 'You can't do that.' "

Toni Preckwinkle (D), a 4th Ward alderman, believes Obama did the right thing, although his maneuver left some hard feelings.

"Alice Palmer and her supporters will never forgive him," she said.

Obama headed to Springfield, where he built alliances with senior Democrats and often worked across party lines. Soon restless, however, he saw a fresh chance when Rush lost a 1999 race for mayor.

By Obama's reckoning, the weakness Rush showed in the citywide race would carry over to his congressional reelection bid. Colleagues and observers say Obama badly misjudged the South Side strength of Rush, a former Black Panther and political veteran.

The contest was never close enough to be tense or tactical. Obama lost by 31 points.

Rush fared especially well in poor and working-class African American precincts. Obama's strength tended to come from upper-middle-class whites and blacks in the tonier neighborhoods of Hyde Park and Kenwood.

"Barack was utterly unable to penetrate the black community," recalled Mikva, an early supporter. "He was still the black professor at the University of Chicago from Harvard."

"It was just a foolish miscalculation. One could call it amateur," said Chicago consultant Don Rose. "What Barack had done over the years, to his credit if not calculation, was make himself known to a wide range of liberal and progressive elements in the city and outside the city. Of course, he's a dazzling kind of guy, and they were dazzled, rightfully so, but all were making the same miscalculation."

For all of Obama's frustration, the race significantly expanded his fundraising network. Although Rush pulled in $804,000 to Obama's $508,000, the challenger raised 23 percent more from individual contributors than Rush, who collected $414,000 from political action committees to Obama's $15,000, according to MoneyLine.

Obama ended the race defeated, dejected and broke, with a personal debt to the campaign of $9,500.

"He didn't seem to get bitter. He didn't turn on people. He engaged people more, and worked it," said Bill Daley, the mayor's brother. He said the loss prompted Obama to retool his game and just might have been the best thing that could have happened. "Then he decided to throw the bomb, and rightly so."

The bomb was Obama's unlikely 2002 decision to shoot even higher -- the U.S. Senate -- against a crowded field of better-known and better-funded candidates. He faced one Democratic rival who vowed to spend tens of millions of his own money and one from a prominent Chicago political family who had already won statewide.

Valerie Jarrett remembers hosting a gathering where Michelle Obama and a few close friends told him he was nuts.

"Walking into that lunch, we were resolved we were going to talk him out of this. No one thought it was a good idea, Michelle being the most clear that it was a bad idea," said Jarrett, a good friend.

The field looked tough and Obama had only recently embarrassed himself. Obama recognized that becoming a two-time loser would likely doom his ambitions. Yet, as he did in 2006 when he decided to run for the White House, he felt sure he had spotted a golden opening.

"I'm willing to gamble. I know if I lose, I'm probably done," Obama said, according to Jarrett. "I have the most to lose and I have confidence that I can win -- and I can't do it without you guys."

They were sold.

Obama ran hard, reckoning that by the primary he had logged 18 months of killer days with just seven days off. He worked black churches and constituencies of all stripes. He drew on his formidable base of contributors. Yet one month before the primary, polls showed Obama with just 15 percent of the vote.

Obama and David Axelrod, his senior adviser then and now, hoarded money for a burst of television advertisements in the final weeks, when voters would be paying closer attention. Drawing on Obama's small-screen charisma to etch a portrait of freshness and principled change, the spots combined an appeal for fairness and civility with references to his legislative record of death penalty reform, expanded health care for poor children and working-class tax breaks.

"What if folks in office," Obama said in one TV spot, "spent their time attacking problems instead of each other?"

"Once we got on television in '04 and everybody saw him, it was like, 'Boom!' " one adviser said. "It changed in no time."

Obama benefited from a significant break shortly before the primary. The divorce file of front-runner Blair Hull, who spent $29 million on the race, revealed allegations of domestic violence.

After Hull's candidacy collapsed, many analysts expected his votes to fall to Illinois Comptroller Dan Hynes, son of a Chicago power broker close to the Daleys. But Obama walloped him, winning 54 percent of the vote in a seven-candidate field, including nine of every 10 votes by African Americans.

The November election was a breeze. Wealthy Republican nominee Jack Ryan dropped out following allegations from his ex-wife that he pressured her to have public sex in nightclubs. The fractured Illinois GOP turned to Alan Keyes, a conservative gadfly who lives in Maryland.

That was the year that Obama became a phenomenon. He delivered an electrifying speech to the Democratic National Convention and raised $15 million. Mostly ignoring Keyes's incendiary attacks, he found himself so far ahead that he jetted around the country to help elect other Democrats.

Obama took 70 percent of the vote in November, beating Keyes by the largest margin in Illinois history.

"He wasn't tested," Bill Daley said. "No one laid a glove on him."

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