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“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 [f---] do you need my two-fifty for? You’re going to raise a billion! Not a hundred million. A [f---ing] 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 [f---ing] 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.”