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After The Convention, Clinton Faces Big Hurdles During The Final Phase Of The Race04:50
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Democratic presidential nominee Hillary Clinton walks on stage after President Obama's speech at the DNC in Philadelphia. (J. Scott Applewhite/AP)
Democratic presidential nominee Hillary Clinton walks on stage after President Obama's speech at the DNC in Philadelphia. (J. Scott Applewhite/AP)
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PHILADELPHIA — On Thursday night, it's finally up to Hillary Clinton. After three days of hearing from ordinary citizens, celebrities and politicians — including her husband and President Barack Obama — Clinton will tell her own story at the Democratic National Convention. Then, starting Friday, the final 14-week phase of the presidential campaign begins.

Among the biggest challenges: Donald Trump's willingness to attack.

"Folks, honestly: She's guilty as hell. She's guilty as hell," Donald Trump said to cheers last month in San Jose, California.

He was going after Clinton's use of a private email server when she was secretary of state.

"The fact that they even let her participate in this race is a disgrace to the United States, it's a disgrace to our nation," he said. "It's a disgrace."

The FBI decided not to seek criminal charges against Clinton, but it did say she'd been extremely careless — giving Trump a big opportunity to attack and feed the narrative that she can't be trusted.

"Well, the biggest mistake I made in 1988 was deciding that I would not respond to the Bush attack campaign," said former Massachusetts Gov. Michael Dukakis, who was the Democratic nominee in 1988.

When his convention ended, polls had him well ahead of George Bush. But then Republicans unleashed a torrent of attack ads calling Dukakis weak on crime. Dukakis didn't respond.

"And it was a terrible mistake," he said. "If the other guy is going to come at you with this stuff, as Bush and Roger Ailes came after me, you just can't sit there and do nothing. And my failure to do that had a lot to do with my losing."

But if Dukakis recommends hitting back, Massachusetts U.S. Sen. Ed Markey says to be careful.

"I think Hillary has to make sure she doesn't fall into a trap as the Republican opponents of Donald Trump did of getting down into the gutter with him," Markey said.

Markey says Clinton needs to respond forcefully, but in a way that makes her look presidential.

"The more that she focuses on the issues and not upon the personality of Donald Trump is the more she's going to make it easy for independents and swing voters to say, 'I think that it's safer to have Hillary Clinton as president,' " he said.

Another big challenge Clinton will face in the weeks ahead is part of what she’ll take on Thursday night with her speech: It’s been said that Hillary Clinton is the most famous politician that Americans don’t know. She’s cautious. Reflexively political. And a bit of a policy wonk.

"Hillary Clinton when she’s in policy mode can be quite compelling, but not particularly funny or emotionally hitting the high notes," said Michael Waldman, who was a speech writer for former President Bill Clinton.

Waldman says the challenge that begins Thursday night for Clinton is to open up.

"I think she’s needs to find a way to reveal more and not be as guarded. I think sometimes she does things where she's not guarded and it sounds guarded, which can be a challenge," Waldman said. "I think, though, everybody says, 'Be authentic! Be authentic! But don’t talk about policy — that’s boring.' Well, she’s really interested in policy, and if you want authentic Hillary Clinton, it’s not the same thing as authentic Donald Trump."

All this puts Clinton in a bit of a bind. And some say it’s evidence that as a woman, she faces a double standard when people urge her to reveal her warmer, fuzzier side. Among them is Casey Steinau, chair of the Democratic Party of Alaska.

"I don’t think anyone thinks Donald Trump is warm or fuzzy for a second. She’s a leader. She’s a boss. She gets it done. Saying that, I think she still has to, to overcome that, which makes things twice as hard for her," Steinau said. "It’s being able to Fred Astaire and Ginger Rogers — Ginger Rogers had to do everything plus [in] high heels, backwards."

One more major challenge that Clinton faces in the weeks ahead: how to tap into the energy of Bernie Sanders supporters. Polls suggest that the great majority of them will vote for her in November — but not all of them. And Paul Feeney, who ran Sanders’ campaign in Massachusetts, says Clinton will need all of them to win in November.

"She absolutely cannot discount the legions of people that have become a part of this process. There's a lot of folks across this country that feel like they found their voice in Sen. Sanders," Feeney said. "Secretary Clinton has to put out an olive branch to them and say that 'We need you.' "

Feeney says Clinton can begin that Thursday night when she accepts her party’s nomination. It will be nothing less than the most important speech of her political career.

This segment aired on July 28, 2016.

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Anthony Brooks Twitter Senior Political Reporter
Anthony Brooks is WBUR's senior political reporter.

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