There’s a fantastic article on the mistake the Clinton campaign made here:
It’s even handed in it’s analysis, I think, and mentions a lot of points I hadn’t considered before. I found this paragraph particularly illuminating:
She chose to accept lobbyist money at a time when her victory was being cast as so assured, that it remained unclear why she needed it. In, she and her husband injected race into the campaign. What was so distasteful was not that the Clintons were racist. On the contrary, it was that they weren’t racist, but were perfectly willing to meddle with race if there was a chance it would translate into political currency. So started the Obama message that Hillary “will do anything” to win. And it resonated.
I think that does a great job of pointing out the image problem Hillary has had for quite some time.