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Obama's Multi-Million Dollar Question: What About The Hillraiser Holdouts?

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Before Hillary Clinton suspended her presidential campaign, the chattering classes were doing what they do best: speculating, specifically about her 18 million voters. Once the New York Democrat bowed out, would her fiercest female supporters "get in line" and support Barack Obama? This question, and others like it, were breathlessly repeated -- as though the simple act of repetition could will a conflict, and a great story, into being.

Barely one month after Clinton's exit from the race, however, the power of the women's vote to stir up trouble for Democrats has become a decidedly less certain affair. While Salon's Rebecca Traister has become an invaluable source for anyone who wants to understand the mixed feelings that still persist among some Clinton supporters, Barack Obama has opened up a double-digit lead over John McCain among women (a trend that started the very week after Clinton brought her campaign to a close). That advantage is sticking, at least according to a new Quinnipiac poll released Tuesday, which showed Obama with a 14-point lead over McCain among female voters.

But even if the process of healing is well underway in the Democratic Party at large, there is less clarity about the status of the "unity project" when it comes to the smaller circle of high-dollar Democratic donors -- many of whom originally backed Clinton. Now, as John McCain begins posting his best-ever financial numbers while the Obama campaign appears to be conceding that small, internet donations can't power them all the way to November 4, the absence of some key "Hillraisers" from the current Obama fundraising effort has become conspicuous. Even a few such holdouts, should they stay on the sidelines for the duration of the election, could add up to a loss of millions of dollars for the Obama campaign and the Democratic National Committee (which is a bit cash-poor, itself).

One former Hillraiser who is now putting his Rolodex to work for Obama said part of the divide in high-dollar Democratic donor circles comes down to gender. "What these [women] are doing is confusing their legitimate anger over sexism that occurred in this campaign -- and particularly in the media -- with the Obama [campaign]," he told The Huffington Post. "I think, as a man, I can't really speak to them about it, even though I feel the same anger about it. I was off the wall about [the sexism directed Clinton's way] during the campaign."

The names of some Hillraiser holdouts will not come as a surprise to those who follow the Democratic money chase. Susie Tompkins Buell, Lynn Forester and Jill Iscol were each cited in background interviews as the key financial workhorses who have yet to start pulling for Obama. In separate conversations with The Huffington Post, the three major donors each described their respective sources of discontent, and talked about what, if anything, can still be done to change their minds.

One area agreement among them, however, rang out loud and clear: the vice presidency should go to Clinton. (Indeed, Iscol already made news earlier this week when she related details of a phone conversation with Obama, in which he appeared to include Clinton on his VP shortlist, to the LA Times.)

"The magic solution in general is the vice presidency. It heals all the wounds immediately," Buell said.

"The smartest thing that [Obama] could do is to make Hillary the vice presidential candidate," Forester agreed.

For her part, Iscol poured water on the notion that women could be similarly moved by the presence of another female candidate on the ticket, such as Kansas Governor Kathleen Sebelius. "Women aren't fungible," she said. "You don't just exchange one for the other."

But even if Clinton is not Obama's running mate, the three former Hillraisers all said the presumptive nominee should make an effort to prop up the Clintons' reputation, particularly that of the former president, which emerged from primary season tarred not only by accusations of racism, but by the sense that his political legacy could easily be discarded on the way to a "new" politics.

"It was a total outrage that the leadership of the party allowed Bill Clinton to be cast as a racist. It was such an injustice -- so stupid and so wrong and so offensive," Forester said. "If he wants to unite the party and bring the true centrists back ... Obama better worry about Bill Clinton's legacy. ... There's a lot he can do at the convention to prove his respect for both Clintons. That would be very, very welcome. If that were done, it would be inevitable that millions of people would support Obama with time, money and votes."

One thing Obama should avoid doing now however, when courting Clinton's big donors, is trying to smooth over hurt feelings among female Democrats by addressing sexism dating from the primaries. "If he was going to [give a speech on misogyny or gender], he should have done it at the time when that was really happening," Buell said. "I think if Barack Obama made a speech right now about gender bias it would be seen as extremely political."

Another lingering resentment for some Hillraiser holdouts is the issue of Clinton's campaign debt. Beyond the practical fiduciary matters and legal wrangling, the whole issue appears to them as a matter of character and tradition, in which the winner of a party primary should help the loser tie up loose ends. "If Hillary Clinton had been the nominee, it wouldn't have taken two weeks to talk about Barack Obama's debt," Forester said.

But while bad feelings persist, Clinton campaign national finance co-chair Yashar Hedayat doesn't think they are destined to last forever. Describing an early Obama-Clinton "come together" session at Washington D.C.'s Mayflower hotel, Hedayat noted that Obama said he could not expect the Hillraisers' "energy and passion" to be transferred to his campaign. "He can have that overnight," Hedayat said -- referring not only to fundraising prowess, but the Clinton grassroots energy -- so long as Obama addresses the fundraisers' concerns about how the former first family has been treated.

Indeed, for the Hillraisers now on the sidelines, it's become a personal affair, even as their former leader urges them to throw all their effort behind the Democratic nominee.

"I haven't had, like, a thought out process I'm following here," Buell said. "I'm just following my heart. Right now, I'm not attracted to anything Obama's doing. There's nothing that's making me feel better about him. ... I've been on these calls with Hillary, where she is very enthusiastically. earnestly trying to convince people that it's time to go in the other direction. I'm not, I can't be. I'm not ready to. ... Obviously, I'm not gonna vote for John McCain. It depends how hard I'm gonna work for [Obama]."

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