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Obama pulled one of the greatest political upsets

“Well?” Obama asked.

“Well,” Margolis recalls replying. “I guess we're going to have to do it the hard way.”

It was never going to be easy. Whatever happens in the general election, Obama's victory over Clinton after an epic 16-month battle for the Democratic nomination will go down as one of the great political upsets of all time.

Just three years out of the Illinois Legislature, saddled with an odd-sounding name and bearing the added burden of race, Obama beat a candidate boasting the party's most vaunted political operation, its premiere fundraising machine and most popular brand name.

It was a triumph of charisma and soaring oratory, two of the oldest commodities in politics, fused with a thoroughly modern campaign that harnessed the Internet like never before.

Obama could not compete with Clinton for the support of the political establishment, so he attracted hundreds of thousands of new voters. He could never out-raise Clinton among party fat cats, so he created an online network of small donors, stunning even his own advisers by raising more than $265 million. He couldn't overcome Clinton's name recognition in big states, at least starting out, so he focused on small ones, a strategy that proved decisive when the nominating contest became an incremental fight for delegates.

He started as an underdog, but that worked to Obama's advantage. His strategists felt free to challenge conventional thinking, like the notion that targeting young people and Republican-leaning states would be a waste of time and resources. Both proved crucial to Obama's success.

The freedom to fail buoyed the Illinois senator and his team when national polls last fall showed Obama trailing by as much as 30 points, leading many political pundits to write him off.

“We didn't have the burden of expectations and a life-long career path,” said David Plouffe, Obama's preternaturally calm campaign manager. “We were very much, ‘If it works out, it works out.'”

Obama also benefited from blunders committed by the Clinton camp, among them the failure to appreciate the importance of the Iowa caucuses; an expectation the race would end quickly, leaving the candidate flat-footed and broke when it didn't; and, perhaps above all, Clinton's decision to run as the candidate of experience at a time when Democratic voters were ravenous for change.

Sitting in his Chicago office, Obama's chief strategist, David Axelrod, pointed to his bookshelf and a copy of “Microtrends,” a slice-and-dice examination of America by Mark Penn, his counterpart in the Clinton campaign.

“There's also such a thing as macro-trends and they are often what define elections,” Axelrod said.

“Elections are generally defined by the incumbent … and rarely do people look for a replica. They almost always look for a remedy and, in (President) Bush's case, that was particularly so,” Axelrod went on. “The question was, was Hillary Clinton really the remedy? It was our supposition, based on everything we could see, and intuition, that Barack represented the starkest departure from Bush and from the kind of politics that people were really recoiling from in Washington.”

All winning campaigns seem brilliant in retrospect. The reverse is true for a losing effort: The mistakes are obvious with the clarity of hindsight. But in Clinton's case, many of them are still startling.

Despite the Clinton campaign's fearsome reputation, many its decision-makers had never worked in a presidential primary. It showed not just in their underestimation of Iowa and other caucus states but in the attempt to run a general election campaign, aimed at the political center, in a contest dominated early on by liberal voters.

Penn's experience helping guide President Clinton to re-election in 1996, with the help of a strong economy and weak GOP opponent, was not like the tough 1992 campaign.

“You had some tremendously talented people, but not a lot who were seriously tested in battle,” said one Clinton loyalist familiar with the inner workings of her campaign.

By contrast, key members of the Obama team – Margolis, Axelrod, national field director Steve Hildebrand, communication strategists Larry Grisolano and Robert Gibbs – had all worked in at least one presidential campaign.