[Hillary Clinton] has talked about not being a natural campaigner. And she has this big shadow because her husband, the former president [Bill Clinton], and President [Barack] Obama both are natural campaigners. And so this is a challenge for her.

Someone cold, politically calculating with no moral compass who can't be trusted. That's what polling and discussions with voters indicate [about Hillary Clinton].

Hillary Clinton and her husband, the former president, are of course by all measures quite wealthy as well, having earned tens of millions of dollars in book royalties and speaking fees in recent years. Which is why in speeches, she leans heavily on her family history.

Judy Price Osgood is a longtime friend of Clinton's, and she says she meets people regularly who say they don't like [Hillary] Clinton.

[Hillary Clinton ] sometimes struggles with the big theme. She loves talking about her plans, and she often is very focused on sort of the smaller things that could be quite valuable in governing but aren't so good in big speechmaking.

Kathy Burgess describes [Hillary] Clinton as fun and an all-around great person but admits it doesn't come through well.

Donald Trump and Hillary Clinton are not themselves members of the middle class, not by a long shot, which means they've searched for other ways to prove to voters that they care about their concerns and understand what middle class workers are going through.