It's the personality, stupid
Jacob Weisberg says Hillary Clinton faces one simple but possibly insurmountable obstacle as a presidential candidate, and it has nothing to do with her husband, her failed healthcare plan or even her gender. The problem, says Weisberg, is that she simply is not likeable, and, for better or for worse, presidential elections are often popularity contests. To wit:
...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 damn problem, and it can't be fixed.