Illustration by Zohar Lazar



David Plouffe sits in his White House office, just a few steps from the Oval, staring at an oversize map of these United States. It’s late afternoon on May 9, two hours after Barack Obama’s declaration that his evolution on gay marriage has reached its terminus. The president is down the hall and on the phone, discussing his decision’s theological implications with several prominent African-American pastors—while Plouffe is being queried about its political dimensions by a querulous Caucasian reporter. The map at which Plouffe is gazing isn’t the electoral kind with the states shaded blue and red; as a federal employee, he notes wryly, “I’m not permitted to have one on the wall.” But given the way his head is hardwired, I’m pretty sure Plouffe is seeing those colors regardless.

The question of whether Obama’s new stance narrows or widens his path to victory in November is one that Plouffe and his comrades have been agonizing over since early this year, when their boss returned from vacation and told them he wanted to take the plunge. The possible political benefits are clear: jazzing up young voters, ginning up gay dollars. As are the costs: turning off socially conservative Democrats and independents, particularly in four pivotal swing states—Iowa, Ohio, North Carolina, and Virginia. But as to the net effect of the announcement on Obama’s ability to accumulate 270 electoral votes, his adjutants are unable to render a firm verdict. “I think there is more upside potential than downside potential,” Plouffe says. “But is there a scenario where it’s harder? Yes.”

Such scenarios don’t rest easily with Plouffe, the nothing-to-chance operative who rose to prominence as Obama’s 2008 campaign manager. Since returning to the fold after a two-year hiatus in January 2011, Plouffe has seen his boss’s approval ratings rise (to a high of 53 percent, according to Gallup, after Osama bin Laden’s killing) and fall (to a low of 38 percent after last summer’s debt-ceiling debacle and the downgrade of America’s credit rating) and rise again. But all along, his message to his colleagues has been the same: 2012 was destined to be a corset-tight election.

The contours of that contest are now plain to see—indeed, they have been for some time. Back in November, Ruy Teixeira and John Halpin, two fellows at the Center for American Progress, identified the prevailing dynamics: The presidential race would boil down to “demographics versus economics.” That the latter favor Mitt Romney is incontestable. From high unemployment and stagnant incomes to tepid GDP growth and a still-pervasive sense of anxiety bordering on pessimism in the body politic, every salient variable undermines the prospects of the incumbent. The subject line of an e-mail from the Romney press shop that hit my in-box last week summed up the challenger’s framing of the election concisely and precisely: “What’s This Campaign Going to Be About? The Obama Economy.”

The president begs to differ. In 2008, the junior senator from Illinois won in a landslide by fashioning a potent “coalition of the ascendant,” as Teixeira and Halpin call it, in which the components were minorities (especially Latinos), socially liberal college-educated whites (especially women), and young voters. This time around, Obama will seek to do the same thing again, only more so. The growth of those segments of the electorate and the president’s strength with them have his team brimming with confidence that ­demographics will trump economics in November—and in the process create a template for Democratic dominance at the presidential level for years to come.

But if the Obama 2012 strategy in this regard is all about the amplification of 2008, in terms of message it will represent a striking deviation. Though the Obamans certainly hit John McCain hard four years ago—running more negative ads than any campaign in history—what they intend to do to Romney is more savage. They will pummel him for being a vulture-vampire capitalist at Bain Capital. They will pound him for being a miserable failure as the governor of Massachusetts. They will mash him for being a water-carrier for Paul Ryan’s Social Darwinist fiscal program. They will maul him for being a combination of Jerry Falwell, Joe Arpaio, and John Galt on a range of issues that strike deep chords with the Obama coalition. “We’re gonna say, ‘Let’s be clear what he would do as president,’ ” Plouffe explains. “Potentially abortion will be criminalized. Women will be denied contraceptive services. He’s far right on immigration. He supports efforts to amend the Constitution to ban gay marriage.”

The Obama effort at disqualifying Romney will go beyond painting him as excessively conservative, however. It will aim to cast him as an avatar of revanchism. “He’s the fifties, he is retro, he is backward, and we are forward—that’s the basic construct,” says a top Obama strategist. “If you’re a woman, you’re Hispanic, you’re young, or you’ve gotten left out, you look at Romney and say, ‘This fucking guy is gonna take us back to the way it always was, and guess what? I’ve never been part of that.’ ”

Photo: From left, Charles Dharapak/AP Images; Kevin Lamarque/Reuters; Official White House Photo by Pete Souza.

Thus, to a very real degree, 2008’s candidate of hope stands poised to become 2012’s candidate of fear. For many Democrats, this is just fine and dandy, for they believe that in the Romney-Republican agenda there is plenty to be scared of. For others in the party in both politics and business, however, the new Obama posture is cause for concern. From the gay-­marriage decision to the onslaught on Bain, they see the president and his team as coming across as too divisive, too conventional, and too nakedly political, putting at risk Obama’s greatest asset—his likability—with the voters in the middle of the electorate who will ultimately decide his fate.

Whichever side is right, one thing is undeniable. For anyone still starry-eyed about Obama, the months ahead will provide a bracing revelation about what he truly is: not a savior, not a saint, not a man above the fray, but a brass-knuckled, pipe-hitting, red-in-tooth-and-claw brawler determined to do what is necessary to stay in power—in other words, a politician.

For a sitting president to be a narrow favorite over his challenger at the start of the general election is on its face unremarkable. But there was no guarantee things would be even this rosy last August, when Obama hit his low ebb. White House communications director Dan Pfeiffer recalls the moment he learned that Gallup had Obama’s approval rating tumbling to 38 percent. “In your darkest moments, you had to wonder if we’d reached a point, like Bush did in the summer of 2005, that you can’t come back from,” he says. “Had we crossed some line where people were saying, ‘We’re just tired of listening to you’?”

The previous eight months had been hell for Obama. After the self-­described “shellacking” his party suffered in the 2010 midterm elections, the president had sought to find a way to work with Republicans, to reestablish the post-partisan métier that animated his election. “For the first part of the year, he played what was largely an inside game,” says Obama’s longtime counselor David Axelrod. “The ideas being (a) maybe we can reason with the Republicans and come to some rational conclusions, and (b) maybe people really wanted to see cooperation. But that obviously didn’t work.”

Not just obviously, but screamingly so, as evinced by the reckless Republican brinkmanship over the debt ceiling and the collapse of the grand bargain on deficit reduction that Obama labored long to fashion with John Boehner. By the time the president took off for vacation to Martha’s Vineyard, recalls a senior White House official, “he was as frustrated as I’ve ever seen him.” Most irritating to Obama was the portrayal of him, on the right and left alike, as a terminally weak leader. “We found ourselves in the worst possible situation,” says ­Pfeiffer, “in which Republicans and some Democrats were using the same talking points to describe the president. That’s a moment of great political peril.”

Even before heading away on holiday, Obama had arrived at a decision to reboot his presidency again. “One thing about him is that he always salvages something from defeat,” Axelrod observes. “He saw we were up against a nihilistic minority; if they were willing to plunge the United States into default, you had to conclude that reason’s not gonna prevail. And we had a fragile economic situation that was exacerbated by their antics. So, for reasons of politics and the economy, he needed to come out firing after Labor Day, lay out an aggressive plan, and take his case to the country. His conclusion was that if we’re gonna move the ball forward, we’re gonna do it by galvanizing the American people, not by trying to cut deals in quiet rooms.”

Obama’s first chance to test-drive his new approach was the speech he delivered to a joint session of Congress soon after returning from the Vineyard. The address was intended to plump for a jobs bill designed, at the president’s specific instruction, without regard for its chances of passage. “I want to put forward what I think the right thing to do is,” Obama told his team. “I don’t want this to be a legislative compromise. We’re not going to negotiate with ourselves. We’re not interested in the possible but in what should be.”

For Obama, the speech proved to be a turning point, politically and personally. “From that moment on, there’s been a sense of liberation about him,” says a confidant of the president. “He’d had enough.”

A cynic might say that the liberation Obama feels is the freedom from, you know, actually governing. And there would be some truth to that. But no one on either side of the partisan aisle disputes that it was Obama’s more pugnacious posture that led to his most important legislative victory of this year: the $144 billion extension of the payroll-tax cut and unemployment benefits that passed in February. For Republicans, the bill’s enactment was an embarrassing defeat, one that put them in the absurd position of first being against a tax cut and then having to buckle in the face of the public pressure fomented by the White House. For Obama, it was a tangible sign of the reclamation of his mojo, the effects of which are still apparent. “The way the Republicans caved on the student-loan issue suggests they have acquired a fear of the president’s capacity to put them in a bad place,” argues Pfeiffer. “In the eyes of the country, he has come to look more like the guy who won in 2008 and less like the image that was being portrayed in August 2011.”

Photo: Christopher Anderson/Magnum Photos/New York Magazine

No doubt that overstates the case. But certainly the winter and spring provided ample cause for Obama to be cheerful. The rising poll numbers. The signs of life in the economy. The anniversary of Bin Laden’s death. And best of all was the sight of a spectacle that would quicken the pulse and gladden the heart of any Democrat in possession of both: the spastic goat rodeo that was the Republican nomination contest.

Few topics provoke such a mix of wonderment, contempt, and glee among the Obamans. On a bright afternoon in early May, Axelrod and I are having lunch in the shadow of One Prudential Plaza, the high-rise in downtown Chicago that houses Obama’s reelection operation. Axelrod is marveling at the jaw-dropping weakness of the Republican field when a news alert hits his BlackBerry. “Speak of the devil: Newt Gingrich suspends his campaign,” he says with a grin. “A landmark day in the history of American politics.”

From the outset, Axelrod and the rest of Team Obama assumed that Romney would ultimately emerge as the Republican nominee, though there were moments of uncertainty. “I believed a well-funded, clever, right-wing candidate could beat Romney,” Axelrod says. “The question was, did anybody fit the bill? Theoretically, Rick Perry was that guy, but he was less than met the eye—he never got the gun out of the holster.”

Perry wasn’t the only Republican whose doofishness caused Obama’s lieutenants to sigh. “All of Romney’s rivals ran incompetent campaigns at every level,” declares Plouffe, nodding appalledly as we tick off the series of malpractice-quality errors they committed, such as the failure to run ads featuring video of Romney signing the Massachusetts health-care law alongside Ted Kennedy. “They had terrible debate strategy, terrible research, and terrible ads. It was painful to see what could be done to Romney and see no one doing it.”

So painful, in fact, that eventually the Obamans decided to do the job themselves, taking the unusual step of becoming participants in the GOP nomination fight, making the arguments his competitors should have been but weren’t. It began with Plouffe appearing on Meet the Press in October and charging that Romney “has no core.” Soon after, the DNC released a two-minute TV ad titled “Mitt Versus Mitt,” hammering its target for being a flip-flopper. “That was the right narrative for him at the time, because it was a fundamental truth, and it damaged him in the primary,” says another Obama adviser. “His negatives went up to the highest of any presidential candidate in modern American history.”

Romney himself, of course, bore the preponderance of responsibility for that fate. The obvious examples are ones where the odd malady from which he seems to suffer—a hybrid of affluenza and Tourette’s—caused him to implant both of his tasseled loafers so far down his gullet that they were tickling his esophagus. But while “corporations are people,” “I like being able to fire people,” “I’m not concerned about the very poor,” his extolling of his wife Ann’s twin Caddies, and his proposed $10,000 bet with Perry would all become part of a greatest-hits reel in the hands of Axelrod’s minions to drive the message that Romney is out of touch, the more important blunders were on policy—and revealed a key weakness in the bargain.

“Romney is thoroughly tactical,” Axelrod notes. “He makes whatever decision he needs to get through the next battle without respect to the war. So he ran to the right of everybody on immigration because he had to beat Perry. He embraced the Ryan budget to get around Gingrich. And then he ran to the right of Santorum, or tried to, on contraception to fend off him.”

Thus did Romney exit the GOP-nomination tussle towing a metric ton of baggage strapped to his bumper, which dramatically weighed down his standing with an array of voting blocs. A mid-April ABC News–Washington Post poll put Obama ahead among women by 19 points, 57-38. An NBC News–Wall Street Journal survey a week later gave him a chasmic 47-point advantage, 69-22, among Latinos and a 26-point lead, 60-34, among voters ages 18 to 34.

It was around that time, not coincidentally, that the Obamans shifted the frame into which they wish to cram Romney: from coreless to, as Plouffe put it to the New York Times, “the most conservative nominee [Republicans] have had going back to [Barry] Goldwater.” To some, the two lines of attack seemed inconsistent: Whatever else might be said of the 1964 GOP standard-bearer, absent a core he was not. Privately, the Obamans admit that the first label was partly a matter of expedience. “It’s not like we could have said, ‘Hey, he’s the most right-wing guy ever’ during the primary,” says one operative. “That would’ve helped him in the primary!”

But Plouffe, recalling George W. Bush’s effective double-barreled attack on John Kerry as both a flip-­flopping phony and a liberal extremist, maintains that the two threads will be merged into a single yarn: “When Romney tries to Etch-a-Sketch, we’re not just gonna say, ‘Oh, there goes old Mitt Romney again! Who knows where he stands?’ We’re gonna say, ‘He is once again showing he’ll say anything—he has no core.’ But we’re also gonna say, ‘We know where he stands; he’s way off to the right on abortion, contraception, immigration, and gay rights,’ and hold him to those positions.”

For Chicago, that task—“freezing him like a bug in amber at the end of the dinosaur era,” as another of the president’s people puts it—is one of the campaign’s paramount strategic imperatives. Another is continuing to remind women, Hispanics, and young voters of Obama’s fealty to them, as he’s been doing tirelessly in the past few weeks, from the campus of Barnard to the set of The View.

Those fat April poll margins won’t be easy to sustain, though—indeed, by the end of May, there were signs that Romney had narrowed all of them, albeit only slightly. According the latest NBC–Wall Street Journal survey released last week, the GOP nominee is now 15 points behind the incumbent with women, 53-38, and is lagging with Latinos by a 34-point margin, 61-27, and with young voters by 20 points, 55-35. Some of this tightening was inevitable, the result of Romney’s no longer being a punching bag for his Republican opponents. But more of it is likely attributable to the issue that voters in every demographic cohort overwhelmingly name as the seminal one—and where Obama is facing a picture not brightening nearly fast enough for his (or anyone else’s) comfort.

Three days after my lunch with Axelrod, Obama arrived in Columbus, Ohio, for a rally to kick off his general-election campaign in earnest. Two days later, his campaign put on the air in nine swing states a 60-second positive ad—backed with a massive $25 million buy of airtime—that echoed one of the two central arguments voiced by Obama in his speech. “Over and over again, [Republicans] will tell you America is down and out, and they’ll tell you who to blame, and ask if you’re better off than you were before the worst crisis in our lifetime,” the president intoned. “But you know what? The real question … is not just about how we’re doing today. It’s about how we’ll be doing tomorrow.”

With this stanza and others like it, Obama was addressing head-on the raison d’être of Romney’s campaign: the contention that you’re not better off than you were four years ago, that Obama is a nice guy in far over his head, a free-spending liberal who has squandered trillions of dollars to scant appreciable positive effect. “What do we have to show for three and a half years of President Obama?” Romney asked in his own speech effectively claiming the Republican nomination. “Is it easier to make ends meet? Is it easier to sell your home or buy a new one? Have you saved what you need for retirement? Are you making more in your job? Do you have a better chance to get a better job? Do you pay less at the pump?”

Obama’s response is to provide context, reminding people of the depth of the turmoil he inherited, and ask them to focus not on the present but the future. Obama’s pollsters have reams of evidence that voters are sympathetic to the first point, and his political people repeat the Clintonian maxim that presidential elections are always more about tomorrow than yesterday.

But Obama’s plea to look forward, angel, would cut more ice if the economy would cooperate a bit more generously and consistently. The Obamans have been praying for circumstances like those that unfolded in 1983–84, in which slow but steady improvement on the jobs front would let them run an updated version of Reagan’s “Morning in America” campaign. Instead what they’ve been handed is a succession of fits and starts and false dawns, in which decent jobs reports are followed by anemic ones, creating in the electorate a widespread and free-floating angst—with just a third of voters saying the economy is improving and nearly two thirds believing the country remains on the wrong track.

Considering all this, the thrust of Obama’s campaign on economic issues will be different from the approach to noneconomic ones. When it comes to the latter, the goal is to keep his lead big with, and drive turnout among, his base; when it comes to the former, the aim is to persuade the small slice of independent voters who vacillate between the parties (maybe 8-to-10 percent of the electorate) in the battleground states to side with the president. According to a recent report by the centrist group Third Way, “swing independents” see themselves as more moderate than Obama, closer ideologically to Romney, but furthest of all from non-Romney Republicans. To Bill Galston, a Brookings Institute scholar and former Clinton adviser, the implication here is obvious: “The Obama campaign should work to ensure that swing voters come to see Romney and the Republican Party as indistinguishable.”

Which brings us to the second central argument in Obama’s Columbus speech: “Now we face a choice, Ohio … After a long and spirited primary, Republicans in Congress have found a nominee for president who has promised to rubber-stamp [their] agenda if he gets the chance. Ohio, I tell you what: We cannot give him that chance. Not now. Not with so much at stake. This is not just another election. This is a make-or-break moment for the middle class, and we’ve been through too much to turn back now.”

In talking about a “make-or-break moment,” Obama was trying to raise the stakes in the election—and thereby make the prospect of changing horses seem riskier. And in calling the race a choice, he was explicitly rejecting Romney’s premise that it should purely be a referendum on his leadership. “Every election is a choice election,” says Joel Benenson, Obama’s lead pollster. “The other guy doesn’t want it to be that way. He wants to talk about macroeconomic numbers and try to make a case about how the president has failed you. Our job is continually to illustrate, expose, and contrast the president’s and Romney’s values and economic visions.”

The contrast part is dead simple: that whereas Obama favors a “balanced approach,” replete with “fairness” (raising taxes on the rich) and investment in the nation’s infrastructure and human capital, Romney is just another proponent of the ultra-laissez-faire-ism that caused the financial system to nearly melt down and brought America to its knees. “Our core argument against him,” says Plouffe, “is that he’s gonna wreck the economy for the middle class. He’s gonna go back to the policies that caused the recession.”

Then there is the exposure part, which entails subjecting the Romney record to withering scrutiny. The assault on his time at Bain has already begun, but soon Chicago will train its fire on his tenure in the Massachusetts statehouse. “He made similar promises in 2002 about what he was going to do for Massachusetts based on his experience in the private sector,” says Obama’s deputy campaign manager, Stephanie Cutter. “ ‘I’ve got all this great experience creating jobs and turning around companies! I’m gonna turn around Massachusetts!’ Well, there’s a reason why he never talks about his Massachusetts record. Because economically, it didn’t work.”

But the Obama indictment of Romney in the economic sphere will extend beyond Bain and the Bay State: It will go to character. It will drive home the idea that Romney is a skillful but self-serving plutocrat whose résumé is replete with self-enrichment but who has never cared an iota about bettering the lives of ordinary people. One tagline that the campaign is considering using—“He’s never been in it for you”—encompasses Bain, Massachusetts, and every Gordon Gekko–meets–Thurston Howell III gaffe he made during the primary season in one crisp linguistic swoop.

“Romney really, actually thinks that if you just take care of the folks at the top, it’ll trickle down to everybody else,” says another Obama operative. “But no one believes that stuff—no one! And once you puncture that, there’s nothing left. He’s not likable. He’s not trustworthy. He’s not on your side. You live in Pittsburgh and you’ve got dirt under your fingernails, who do you want to have a beer with? It ain’t fucking Mitt Romney. You’re like, ‘Shit, I’d rather have a beer with the black guy than him!’ ”

The degree to which Obama’s people see Romney as a walking, talking bull’s-eye is hard to overstate, as is their contempt for his skills as a political performer. The outlier among them in this regard is Jim Messina, the president’s campaign manager—not because he disagrees, but because it’s irrelevant to the plan he is trying to execute. When I ask Messina if Romney is a more formidable foe than McCain, he replies without blinking, “I don’t care.”

It’s another gorgeous May morning in Chicago, and we are sitting in Messina’s office, with its postcard view of Millennium Park below. At 42, Messina is an invisible man compared with Axelrod and Plouffe, though his role in the 2008 campaign, when he served as the latter’s deputy, was nearly as critical. Messina served for years as chief of staff to Montana’s senior senator, Max Baucus, and later as deputy White House chief of staff in Obama’s first two years. He earned a reputation as a very nice guy who would merrily club you with a truncheon if you crossed him. In addition to not caring about Romney’s candidate skills, he doesn’t give a whit about national polling, in which Obama’s numbers are dragged down by his horrific performance in the Deep South and Appalachia—but is obsessed with the president’s standing in the battleground states, where Obama has “a distinct advantage,” he says, “and everybody, including Mitt Romney, knows it.”

Back in December, Messina laid out publicly the ways that advantage gives Obama an upper hand when it comes to the Electoral College: four mathematical scenarios by which he could get to 270 while underperforming 2008. (A fifth scenario involved him expanding the playing field, about which more in a moment.) The safe presumption underlying each is that Obama holds the nineteen states plus the District of Columbia that John Kerry won in 2004—which, recall, did not include Colorado, Florida, Indiana, Iowa, New Mexico, North Carolina, Ohio, or Virginia, all of which Obama carried in 2008, giving the president a base of 246 electoral votes. There’s the western path: Obama holds Colorado, New Mexico, Nevada, and Iowa for a total of 272. There’s the midwestern path: Obama holds Ohio and Iowa (270). There’s the southern path: Obama holds North Carolina and Virginia (274). And there’s the Florida path, in which Obama simply again takes the Sunshine State (275).

I ask Messina if all four avenues are still open. “Absolutely,” he replies. “The West path is completely operative. The Midwest is there; I believe that we’ll carry Ohio and Iowa. We lead in Virginia and North Carolina today; so that pathway’s there. We are tied in Florida; so that pathway’s there.”

Messina and I were talking a few days before Obama’s gay-marriage decision, which, because of its impact in Iowa and North Carolina, would leave his people feeling more pessimistic about both the midwestern and southern paths. (And because of the foreclosure crisis and other economic factors, they are worried about Florida, too.) In truth, the most promising of all the routes to 270 is the western one, because of the dominant lead Obama possesses over Romney with Hispanics. Indeed, if you factor in New Mexico, which the president nabbed in 2008 and is considered safe this time, and Virginia, which has a sizable Latino population, a relatively strong economy, and polls consistently showing Obama ahead, he can hit 270 without winning Iowa, Florida, Ohio, New Hampshire, or North Carolina.

This is an amazing fact—and one that throws into stark relief the converse difficulties Romney will have in reaching the magic number. The dauntingness begins with his initial hurdle to surmount: clawing back at least six states Obama won last go-round. Almost all of Romney’s 270 scenarios revolve around a strategy outlined by Karl Rove and dubbed “3-2-1,” in which the GOP reclaims three of the traditionally red states snatched away by Obama (Indiana, North Carolina, and Virginia), wins the two perennial mega swing states (Florida and Ohio), and then snags one more from among those up for grabs.

A senior Obama campaign official scoffs at the notion that Romney could pull off such a feat. “To get there,” he says, “they’ve got to take away either Pennsylvania or Michigan, and they can’t do either one of them. Michigan is a motherfucking joke, to think they can do that, because of what he’s done on the auto stuff. And in Pennsylvania, we have a 900,000-person registration advantage. John Kerry had 250,000; we had 900,000 more Democrats than Republicans on the first day.”

As for the western states, Messina believes Romney’s problems with Hispanics are insoluble, although he, like everyone else on Team Obama, anticipates a vicious ad barrage aimed at depressing Latino turnout. “I expect to see what I’ve seen in the primaries, which is their super-PACs spending an impressive amount of money completely negative,” he tells me. “I expect us to counter that the way Harry Reid did [in his 2010 reelection battle]—with a full discussion of the issues and a huge ground game.”

In truth, the unprecedented flood of dollars that is about to engulf the presidential race—and the near certainty that the majority of them will be spent by the Republicans—is what keeps Messina and his brethren awake at night, gnawing at their fingernails like a pack of feral crystal addicts after a hellacious weeklong binge. And while the Obamans talk assuredly about how the effect of the TV ads can be counteracted by a robust turnout operation, the financial pinch is already being felt in terms of their strategy. When Messina detailed Obama’s pathways to 270, for example, the fifth option involved playing full-out in Arizona, whose large Hispanic population should make it ripe for the picking and where public polling shows Obama and Romney in a dead heat. But that possibility remains on hold, seen as a bridge too far (at least for now) for a campaign that desperately needs to husband its resources.

“The money is a huge problem,” confides a senior campaign maven. “We’ll see how long we can stand it. The money alone can’t beat us, but if we get bad jobs numbers a couple months in a row, then all of a sudden, things could get kinda hairy.”

That Obama should find himself on the losing end of a dash for cash is, to anyone familiar with his 2008 campaign, mind-boggling. Four years ago, the upstart candidate had the temerity to take on not only Hillary Clinton but the Clinton fund-raising juggernaut—and kick its ass. The mythology today is that the prodigiousness of Obama’s buckraking was all due to small donors and the juju of the web. Not so. Obama went toe-to-toe with Clinton in competing for Wall Street donors and whipped McCain among the Masters of the Universe. And the expectation was that his fund-raising prowess would be all the greater as a sitting president. Obama would raise $1 billion. His White House–sanctioned super-PAC would haul in at least another $100 million. Obama might fail to secure reelection, but his team would never find itself in the position of hoarding its pennies.

And yet here we are. Although Obama is surely raising a boatload of dough, it appears his campaign (combined with the DNC) could fall short of its goal of $750 million. (Its April fund-raising total declined to $43.6 million from $53 million in March.) Meanwhile, the pro-Obama ­super-PAC, Priorities USA Action, has raised less than $10 million since setting up shop more than a year ago—$2 million of it from Jeffrey Katzenberg—leading a highly placed Democrat involved in the reelection effort to describe it to me as a “fucking abysmal failure.”

Bill Burton, the former White House deputy press secretary who is one of two men running the super-PAC, disagrees. It’s still early, he says, and professes “no doubt” that his group will reach its $100 million target. But Burton allows that the task has been harder than he anticipated. “We had to spend a year talking to donors, educating them about why super-PACs would matter, even though in 2008, I, as the president’s spokesperson, and the president himself were saying, ‘Do not give to outside groups,’ ” he says. “And we had to do that with the group of people who are automatically skeptical of money in politics.”

But one of the most vaunted fat-cat-wranglers in Democratic history tells me that this is only part of the story. “There are several things going on,” this person explains. “Number one is the shabby treatment the president has given his donors. Unlike Clinton, who loved them and accommodated them, Obama announced he didn’t like big money and gave them the back of the hand. Point two is the president’s campaign announced—or not announced, they let it out, it got in the press, it got in the ether—that they were going to raise $1 billion. So when they come to you and say, ‘We need two-fifty,’ the answer is, ‘What the fuck do you need my two-fifty for? You’re going to raise a billion! Not a hundred million. A fucking billion dollars!’ You’re getting into federal-budget territory with that kind of claim.

“Three is the Obama donors aren’t scared. They think this is a slam dunk. They don’t think the president’s in trouble. They look at the Republican-primary process and say, That group of fucking clowns? Fourth, Burton and his partner are great guys, but they have no experience in fund-raising. They thought that with the patina of the White House, the checks would just roll in. Wrong.

“Then, everybody looks to George Soros. ‘Why won’t George throw in?’ I know George pretty well. Early on, he wanted to come in to make his case on the economy. George doesn’t want legislation tweaked. He doesn’t want a rule changed. He wants his ideas heard out. But George couldn’t get a meeting in the White House. And then George is saying, ‘Where are the Obama money people with their 5 and 10 million dollars? Where is Penny Pritzker, Exhibit A? Why isn’t she throwing in 10 million?’ And that is a very good question.”

A prominent private-equity player in Gotham who supports Obama agrees with all of that but adds another insight. “Among rich Republicans, the view of Obama is that he’s the Devil,” this person says. “But on the Democratic side, certainly on Wall Street, there’s no visceral reaction against Romney. So if I give $10 million, I’m out the $10 million, and I’m gonna pay more in taxes if Obama wins. And I’m doing it against somebody who—I may not agree with his social views, but I don’t think he’s a bad person. And I’m not really into negative advertising, which is what a super-PAC would do … Then there’s the fact nobody on Wall Street thinks Obama gives a shit about them. They think his attitude is, ‘If I lose Wall Street, it’s not the end of the world.’ And they’re right.”

Whatever the causes, the consequences for Obama may prove dire. Burton reckons that, in the end, the cumulative spending on the Democratic side will be about $1 billion, compared with maybe $1.6 billion on the Republican side. And while the latter may be exaggerated for effect—other savvy Democrats put the GOP figure at more like $1.3 billion—there’s little doubt in either partisan camp that we are about to witness the improbable development of an incumbent president’s being financially overmatched.

“It concerns me gravely,” Plouffe tells me. “From a political standpoint, I’m almost as worried about that as I am about the question of what the economy’s gonna do over the next three or four months.”

Axelrod is endeavoring not to panic. “We don’t know yet how big a problem it will be,” he says. “We’re actually about to test the limits of what money can do in politics, because there’s gonna be so much of it concentrated in so few states. The real question is, at what point is so much too much?”

For anyone unlucky enough to reside in a battleground state, the answer is obvious: all too soon. (“You should give your TV to a friend,” Messina helpfully suggests.) But inherent in Axelrod’s query is an important point. Though political advertising matters a great deal in statewide races, its effect on presidential contests tends to be more muted, with the wall-to-wall news coverage on the air, in print, and online mattering far more. And ads are prone to be even less consequential when it comes to an incumbent, with whom voters have been living nonstop for nearly four years and of whom impressions are fairly deeply burned in. In the words of one Democratic media consultant, “How many times and how many different ways are you going to say, ‘Obama wrecked the economy’?”

And there is another possibility—one suggested by the storm of controversy around the proposal to superrich conservative Joe Ricketts that he finance an ad campaign focused on the Reverend Jeremiah Wright. Even when outside groups are run by people in possession of their faculties, they pose a challenge to campaigns in terms of maintaining strategic coherence. “Which is exactly why in 2008, we told our donors not to give to third-party groups,” a veteran of Obama’s first campaign says. “We were terrified of the inability to control message and where it would take us.”

With an assortment of right-wing magnates both champing at the bit and suffering from Obama Derangement Syndrome, the super-PAC phenomenon may wind up inducing migraines in Romneyworld—and even in some cases redounding to Obama’s benefit, as it did with the Wright proposal. “Our reaction was, ‘Fucking bring it on!’ ” says the same Obama veteran, who is involved again this time. “It let us raise some righteous indignation in our base, send a shot across the bow to corporate leaders thinking of giving to these super-PACs, and go to African-American leaders and say, ‘Hey, you need to go out there! Threaten boycott against TD Bank! Do whatever you have to do to push back and gin up our side!’ ”

Nothing could more garishly illustrate a bedrock truth about the campaign that lies before us: It will bear about as much resemblance to 2008 as Romney does to Nicki Minaj. In the campaign prior, any mention of Wright caused a collective coronary in Chicago; this time, it provokes high-fives. In the campaign prior, Team Obama boldly bid to expand the map; this time, it is playing defense. In the campaign prior, the candidate himself sought support from the widest possible universe of voters; this time, instead of trying to broaden his coalition, he is laboring to deepen it. Indeed, 2012 is shaping up to be an election that looks more like 2004 than 2008: a race propelled by the mobilization of party fundamentalists rather than the courtship of the center.

If Obama wins a second term this way, the implications for governing could prove salutary—or god-awful. The president, energized by the prospect of a debate about “big things,” purports to take the optimistic view. “I think the general election will be as sharp a contrast between the two parties as we’ve seen in a generation,” Obama told Rolling Stone. “My hope is that if the American people send a message to [the GOP] … there’s going to be some self-reflection going on—that it might break the fever.” And, hey, who knows, crazier things have happened. Likelier, though, is that an incessantly negative, base-driven election will yield an uglier outcome. More polarization. More acrimony. More gridlock. (Yippee!)

What’s clear is that an Obama victory could have profound political implications for the future of the Democratic Party. When 44 arrived in office, some forecast that he might usher in a New New Deal. (Nope.) But if he gains reelection by consolidating his party’s position with the electorate’s ascendant demographic forces, Obama may succeed in creating a viable post–New Deal coalition on which Democrats can build for years to come. “Ronald Reagan turned a whole bunch of people who are now seniors into Republicans,” says Messina. “What is happening now is that young people, women, and Latinos are becoming Democrats. That’s the coalition Obama brought; demographics brought it, too. And for the next 30 years, it is going to be a real challenge for Republicans.”

Of course, if Obama loses, all such grand talk will be consigned to the ash heap of history—and hubris. And there are plenty of Democrats more jittery about that possibility than they were just a month ago. To their eyes, the president’s team seems off-kilter, his campaign off-brand, his rival finding his stride. “The natural gravity of this race is such that Romney will be close or a little bit ahead very soon, and it’s going to be like that through the convention,” says a Democratic strategist. “Romney doesn’t have idiots working for him; they’re going to run a safe, smart, tactical campaign.” And they have proven adept at one thing: “They kill well,” admits a senior White House official. “And that’s not unimportant.”

Amid all the chatter from the peanut gallery, the Obamans are keeping their eyes on the prize. In 2008, their campaign’s motto was “Respect, Empower, Include.” In 2012, at the direction of the president, a fourth word has been appended: “Win.” For all their brio, Obama’s people know their campaign could be derailed by myriad events outside their control: dismal job numbers, a spike in fuel prices, hostilities in Iran, an economic shock from Europe, the overturning by the Supreme Court of health-care reform.

Are the Obamans nervous? Healthily so, but they are also buoyed by a firm conviction. As Plouffe puts it, “This is going to be a very close race, but I’d rather be us than them.”

Additional reporting by Clint Rainey.