[Judy Price] Osgood was among about half a dozen [Hillary] Clinton friends who I sat down with more than a year ago before she announced her candidacy.

Way back in 1979, as a guest on a local TV show in Arkansas, then Hillary Rodham was quizzed about not taking her husband's last name when they got married and keeping her job as a lawyer while being first lady of the state.

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.

People don't change. People are who they are.

She [Hillary Clinton] says I know that this is the first time that one of our two major parties has ever nominated a woman, and that takes some getting used to even for me. And I think that she has to somehow figure out a way to talk about it. She doesn't like being a symbol, but in many ways, that's what tonight is about.

Trump has a pretty remarkable ability, going back to when he was in business, to reframe defeats as wins. So he had four business bankruptcies and he found a way to say that those are actually wins for him.

The theft potentially of data does create this image of sort of cloak and dagger politics that we sort of imagine when we think of underhanded politics.

[Hillary Clinton] needs to accomplish a lot. She also has to provide a unifying theme for all the things she wants to do.

President Trump is a brand. President Trump is more popular than Republicans in Congress among Republicans.

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

I don't think that [Hillary Clinton] can turn around her honesty and trustworthiness problems with one speech, but she could present herself tonight as more relatable, give people a glimpse of that warm, funny woman the people who meet her in small groups and one-on-one say that she is.

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.

At the Republican convention, there were lots of words used to describe Hillary Clinton, but warm, funny and caring weren't among them.

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.

Aside from Donald Trump, polls find [Hillary] Clinton to be the least-liked presidential candidate in recent history.

[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.