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It’s difficult to overstate Barack Obama’s achievement in wresting the Democratic presidential nomination from Hillary Rodham Clinton—or the magnitude of the gamble he represents for his party.

Obama is the first true insurgent to win either major party’s nod since Democrat Jimmy Carter in 1976. In the modern primary era, the only other insurgents to capture nominations were Republican Barry Goldwater in 1964 and Democrat George McGovern in 1972. And none of those three defeated a front-runner as formidable as Clinton. Obama’s campaign will likely be remembered as the most successful primary insurgency ever.

That itself defines some of the Democratic gamble. An insurgent campaign inherently upsets existing arrangements and assumptions. It trades the comfort of the familiar for the exhilaration and unpredictability of the new. Obama’s campaign is no exception. He offers Democrats new electoral opportunities with the enormous passion and activism he inspires. But his hold on some voting blocs and states that the party traditionally targets looks shakier than Clinton’s might have been. Obama almost certainly presents Democrats with a better chance to redraw the electoral map and expand their coalition if all goes well. But, in a year so tilted toward Democrats, Clinton might have represented a safer bet to accumulate the bare minimum of 270 electoral votes needed to win the White House. Compared with Clinton, “Obama has a much bigger upside,” says Robert Borosage, co-director of the liberal Campaign for America’s Future. “And a much bigger risk.”

That’s evident on every front, starting with demographics. Obama’s magnetic appeal to young people offers Democrats a chance not only to generate a big winning margin in November but also to cement a generation’s lasting allegiance, much as Ronald Reagan did for Republicans in the 1980s. Obama should also inspire a huge African-American turnout. And with a message focused on transcending partisan divides, he could help Democrats solidify their 2006 gains among independents, especially the well-educated ones who flocked to him in the primaries. “He could really consolidate that movement,” Borosage says.

But cumulatively through the primaries, exit polls found that Obama won only 35 percent of the Latino vote, 35 percent of the Catholic vote, 30 percent among whites without college degrees, and 28 percent among white seniors—groups that the party typically relies upon. He also faces doubts among Jews, a small bloc that might nevertheless tip the scales in Florida and Pennsylvania. Early polling diverges on whether Obama could run as well as Clinton among those constituencies against presumptive GOP nominee John McCain. Even if the answer is no, Obama could offset any erosion by posting gains in his demographic strongholds. But his struggles with such groups as Latinos and working-class whites increase the odds that he will need to assemble a new coalition to win, probably one tilted more upscale than usual for Democrats. “At the beginning, I thought we would rather run against Hillary,” one top GOP operative says. “But it is more of a challenge for him than for her to put together a coalition.”

Obama may need to construct a new geographic model, too. Either Obama or Clinton would have pursued Iowa and New Mexico. Her next tier of targets would have included Ohio, Arkansas, and even West Virginia, lunch-bucket states that all voted for Bill Clinton twice. Obama’s difficulties among blue-collar whites make him a tougher sell in those states. That makes it more likely he will need to win Virginia or Colorado, which are trending Democratic but between them have voted for the party’s presidential nominee just once since 1964.

The same contrast extends to their personal profiles. Both Clinton and Obama are history-making candidates, but electing the first African-American president might be an even greater leap than electing the first woman. Obama is stronger thematically: As a young, mixed-race candidate, he uniquely embodies his core messages of change and reconciliation. But Clinton, with her eight years as first lady, might have more easily crossed the experience threshold.

The common theme here is that Clinton’s potential route to the White House was one that Democrats have followed successfully before. For Obama to win, he probably will need to blaze new paths. That doesn’t mean he can’t, or won’t, do exactly that. It just means that in a year that Democrats might have been tempted to play it safe, they have opted for a candidate who could transform American politics—or leave his party second-guessing itself for ages.