A Slate perspective:
But Why Can't Hillary Win?
Sen. Clinton's electability problem.
Political insiders mostly agree: Despite being an early front-runner for the 2008 Democratic nomination, Hillary Clinton faces long odds of ever being elected president. But if she can't win, why can't she?
In fact, Sen. Clinton's political positioning couldn't be better for 2008. Despite being a shrewdly triangulating centrist on the model of her husband, she remains wildly popular with the party's liberal core: It seems to share the right's erroneous view of her as a closet lefty and draws closer to her with every inane conservative attack. There's no other possible candidate in either party so well poised to claim the center without losing the base.
Well, if she is so well positioned, then why the consensus that she just cannot win?
Yet Hillary does face a genuine electability issue, one that has little to do with ideology, woman-hating, or her choice of life partner. Plainly put, it's her personality. ... But she still lacks a key quality that a politician can't achieve through hard work: likability. As hard as she tries, Hillary has little facility for connecting with ordinary folk, for making them feel that she understands, identifies, and is at some level one of them. You may admire and respect her. But it's hard not to find Hillary a bit inhuman. Whatever she may be like in private, her public persona is calculating, clenched, relentless—and a little robotic.
...And a case can be made that the first woman who gets elected president will need to, as Hillary does, radiate more toughness than warmth. But in American elections, affection matters. Democrats lost in 2000 and 2004 with candidates Main Street regarded as elitist and aloof, to a candidate voters related to personally. Hillary isn't as obnoxious as Gore or as off-putting as Kerry. But she's got the same ... problem, and it can't be fixed.
Interesting, and difficult to disagree with. Although I am personally not sure that Sen. Clinton is electible, given the current political climate, I would agree with the notion that the first woman who gets elected President will garner more respect than adoration. In other words, she'll have to be tougher than most.