Anxious Obama plans fundraising spree

President Obama will host a series of high-dollar fundraisers in the coming weeks and is expected to add more events than usual after the Democratic National Convention.

The string of upcoming events reflects deep worry in Chicago about competing with the tidal wave of cash being raised by outside groups aimed at electing Mitt Romney.

The impetus for more and more big fundraisers just 98 days before the election is also in stark contrast with where Obama was in his matchup against Sen. John McCain (R-Ariz.) in 2008, when he had a substantial financial advantage fueled by individual donations.

Obama has spent a considerable amount of time fundraising in recent days.

On Monday afternoon, he flew to New York to attend a fundraising dinner with 60 attendees at a cost of $40,000 per person. The trip came on the heels of high-dollar fundraisers in Washington, D.C. and Virginia on Friday, after a week of attending several fundraisers on the West Coast — including the campaign’s honey pot in Northern California.

Romney has also continued to attend his fair share of fundraisers, including two check-collecting stops in England and Israel.

But sources close to the Romney campaign say they expect to shift away from constantly hosting fundraisers, moving toward more public rallies and events in the weeks before Election Day, believing the priority at that point should be engaging swing voters with rallies and public appearances.

Obama and Romney are both in furious pursuit of campaign cash to fuel political ads. In the most recent spots, Romney’s campaign is hammering Obama over his “you didn’t build that” remark, while Obama’s campaign is responding with more attacks on Romney’s record at Bain Capitol.

The crush for cash could add more fundraisers to an already dizzying schedule for the president. 

Asked whether Obama would shift to do more fundraising or host more rallies in the coming weeks, a campaign official — careful not to get ahead of the president’s schedule — said to “expect a balance of events, a combination of different kinds of events” for the foreseeable future. 

But other sources acknowledged that the pressure to get more cash by putting Obama in front of donors is great.

Don Peebles, a member of Obama’s Finance Committee, added that “there’s a big push to keep the president competitive financially” during the final stretch of the campaign, especially in the face of super-PACs’s massive fundraising.

“It’s just a reality of the campaign-finance situation as we have it,” said another top Democrat who is working with one of the outside groups helping to reelect the president. “

“If you’re facing a flood of cash, you’re going to have to spend more time fundraising than in the past,” this source said.

Democratic strategist Karen Finney — also a contributor to The Hill — said the expected increase in events is “certainly unique to this [election] cycle” and that it’s largely due to the money being raised and spent by outside groups including Karl Rove’s American Crossroads and its Crossroads GPS affiliate.

“You just can’t take anything for granted this cycle, and seeing the unprecedented amount of money being spent, it’s not surprising that he will have to continue to stay competitive,” Finney said. 

According to a Republican fundraiser, Romney should have more flexibility to move away from big-dollar fundraisers because his campaign has placed a high priority on getting donors to write large max-out checks early in the campaign. By incentivizing a single maximum donation — offering exclusive access to candidate retreats or inauguration events — the campaign doesn’t have to spend multiple days courting the same group of donors over and over again, freeing Romney to either appeal to new financial supporters or spend more time on the trail.

That aggressive fundraising style was apparent during Romney’s foreign trip this week. While Obama did not attend any fundraisers during his 2008 trip overseas, Romney attended the pair of million-dollar events.

Romney will also be aided by the fundraising prowess of the conservative super-PACs, which have demonstrated time and again their ability to quickly infuse huge sums of cash into the race. With motivated billionaires like Sheldon Adelson and the Koch brothers having already pledged to spend whatever is necessary to help defeat Obama, Romney can rely on outside groups to maintain balance on the airwaves. 

Obama’s senior campaign aides have long acknowledged that they face an uphill battle in terms of campaign cash, something even the president acknowledged recently on a conference call with donors.

“If things continue as they have so far, I’ll be the first sitting president in modern history to be outspent in his reelection campaign,” Obama said.

In a fundraising plea Monday, Vice President Biden warned supporters that “if we don’t win this election, it will be because we didn’t close the spending gap when we could.

“In the last two weeks of this month, Romney and his allies had an almost 2-to-1 spending advantage in Florida, Iowa, New Hampshire, North Carolina and Virginia — and that could be the election right there,” Biden said. “We’re running out of time to close the money gap when it really matters.”

In a column on Monday, Juan Williams, a political analyst for Fox News, surmised that Obama could make news in an “October surprise” announcing that his campaign is “out of money and unable to answer the final round of attack ads from his opponent, Mitt Romney.”

“This scenario is no longer outside the realm of possibility,” Williams wrote in a column in The Hill.

Obama supporters acknowledge that cash still might be the campaign’s heaviest lift.

“Cash is the biggest problem we face,” said one former senior administration official. “The notions of traditions in presidential races need to be completely wiped clean. This election became completely off-set with the super-PAC ads. It’s unlike anything we’ve ever seen.

“While the last campaign was sealed by individuals, now it’s corporations,” the former official said.