The mood of many Democratic contributors is likely to make the job more awkward than usual. Obama's three-day fundraising swing down the West Coast, which begins today in Seattle, will bring him face-to-face with frustrated donors who have watched the botched rollout of the Affordable Care Act with chagrin -- and who are not shy about expressing their alarm.
The crisis has left the party's major financiers shaking their heads, compounding the challenge for the Democratic National Committee as it works to pay down $16 million in debt from last year's campaign, according to top fundraisers and donors.
Without a campaign to rally around, donors have to be energized to help execute a specific mission, said fundraiser David Rosen, a former DNC finance director. And right now, many are feeling glum.
"My ideological donors are so demoralized with health care, you can't even talk about it with them," Rosen said. "They're business people -- you don't launch until it's ready."
Obama is still expected to raise millions of dollars for the DNC and the two congressional party committees when he stops in Seattle, San Francisco and Los Angeles. He will be feted at the homes of former Microsoft executive Jon Shirley, entertainment mogul Haim Saban, basketball star Magic Johnson and "Friends" co-creator Marta Kauffman.
In San Francisco, supporters were able to get last-minute tickets for $500 for a DNC lunch and concert with Herbie Hancock on Monday at the SFJAZZ Center, half the price of the original general admission. A DNC official said the lower-priced tickets were added because balcony seating was opened up to accommodate demand.
The president can expect an earful from those he encounters in the VIP receptions and photo lines. Hollywood writers have notes on how to sharpen the White House messaging strategy. Technology executives have ideas for fixes to HealthCare.gov and complaints about the data collection programs of the National Security Agency.
After the shaky debut of the federal health insurance exchange, "absolutely, there are insiders who say, 'I'm going to be less supportive now,'" said a person involved in the planning of one of the West Coast events. "But the vast majority of people are still drawn toward wanting to have some kind of contact and relationship with the administration and toward being part of solution."
Indeed, some donors said they view the technical problems as short-term hurdles.
"No one is happy about the website glitch, but I don't think any one of us have been fazed by that," said Florida lawyer Ralph Patino, who hosted Obama at his Coral Gables home for a DNC fundraiser this month. "We're staunch supporters of the president."
Confidence is 'fragile'
Their confidence is "fragile, but holding," said one well-connected Democrat plugged into the thinking of some of the biggest contributors on the left, among a half-dozen who described the mood of donors. "They're worried about how this is going to hurt people in the midterms, but they're not down on him."
But others said the fumbled start of the healthcare law has intensified disappointment among some big check-writers that has been building throughout the year, deepening the usual fundraising drop-off that follows a presidential election. Many liberals were particularly alarmed by Obama's push for a military strike against Syria and by revelations about the NSA's vast data-gathering operations, according to party fundraisers.
Uncertainty about whether Obama will approve the Keystone XL oil pipeline has also made many supporters nervous.
"The problem has been the domino effect: first Syria, then NSA, then HealthCare.gov," said one major Democratic fundraiser. "He hasn't had any good news wins to offset those."
By going to the liberal Bay Area, where donors are known for confronting politicians with frank talk, Obama is guaranteed to face some tough questioning, said longtime Democratic strategist Chris Lehane.
Some of those queries are likely to come from technology executives who will attend a private roundtable discussion Monday at the home of Salesforce.com chief executive Marc Benioff.
"At every event, there will be at least three hard questions: One on Keystone and climate change, one on spying and some version of 'How do you break the paralysis in D.C.?'" Lehane said.
The shaky health-care debut has come at the same time that Obama has been on a national fundraising spree, trying to make up ground after the government shutdown and other crises forced him to cancel earlier donor events.
Since late October, he's made stops in New York; Weston, Mass; Dallas; South Florida; and Philadelphia to raise money for the three party committees. After this week's trip to the West Coast, the president will have headlined 17 events in a month, according to a tally by The Washington Post.
That schedule has put him in the position of soliciting checks in the midst of an intense damage-control operation.
On Nov. 14, just hours after offering repeated mea culpas in a long White House news conference, Obama stood in a large white tent in the back yard of Comcast executive David Cohen's Tudor-style home in Philadelphia, addressing donors at a fundraiser for the Democratic Senatorial Campaign Committee.
"This may be counterintuitive, but the mood was extremely upbeat," said Peter Buttenwieser, a philanthropist and education consultant who helped organize the event.
"I don't want to imply that people are not concerned" about the rollout of the health-care exchange, Buttenwieser said. "But this particular evening was a way of saying to the president, 'We stand behind you in difficult times.'"
Donors have generally been enthusiastic about backing the DSCC and the Democratic Congressional Campaign Committee, which are both on track to raise the most money ever in a non-election year.
But the climb is much steeper for the DNC, which has raised $53 million through October compared with nearly $64 million collected by the Republican National Committee. So far, the DNC has paid off only $5.5 million of $21 million in debt it was left with at the end of 2012.
DNC spokesman Michael Czin said the party's fundraising has improved over the past two months, buoyed by big-dollar fundraisers and a record amount of online donations.
"We have momentum," Czin said. "We think we're well-positioned headed into 2014, and we're working to retire that debt."
Still, party fundraisers said that it has been hard to get major contributors jazzed about writing checks to the DNC. They are more intrigued with 2016 and whether Hillary Clinton will make another White House run.
"I get dozens of inquiries from donors who say, 'I want to get in early with Hillary,'" said a prominent party fundraiser. "A lot of the donors are starting to look past this administration to the next one."
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