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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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"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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