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For Obama, a Handsome Payoff in Political Gambles

In 2000, Illinois Democrats were backing Al Gore and Joe Lieberman. In 2007, it's Barack Obama, the man behind Mayor Richard M. Daley, right, who wants to be president. Obama has a history of being able to spot the golden openings in running for political office, and his advisers are confident he can win.
In 2000, Illinois Democrats were backing Al Gore and Joe Lieberman. In 2007, it's Barack Obama, the man behind Mayor Richard M. Daley, right, who wants to be president. Obama has a history of being able to spot the golden openings in running for political office, and his advisers are confident he can win. (By Stephen J. Carrera -- Associated Press)

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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."


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