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I agree with you that it would help him politically with Dems and women, no doubt. And she's a champ at fundraising herself, so she would most definitely recoup the money for him and then some. She's probably got a long list of potential deep-pocketed donors and a mailing list a mile long. She would be a big asset.

But I can't help feel queasy about the idea of her campaign being bailed out like that. As much of an asset as she is, she's also a liability, especially in this case. He does this and he's handing McCain the gun to shoot him with. They were already going to paint him as a 'tax and spend' liberal(that's how they've run every campaign since Goldwater), but if he pays off her campaign's debt it will be that much easier to get that message across that that's how he'll govern, as well. Hell, there's already been a post on this thread about it. Many Americans actually think the president has command of the budget(he does not, technically) and would buy that line of bullshit. And those people would switch to McCain.
Obama(like McCain) needs to worry about the people that are iffy on him, not the ones who're going to vote for him anyway. This could be a close election if he makes errors like this. Right now, the only one who can beat Obama is Obama.