Hillary Clinton has expressed frustration, and even a little trepidation, about her first face-off with Donald Trump later this month, recently telling one person close to her that she’s perplexed about "which Donald Trump will show up.”

And she has told friends since the spring, at fundraisers and in private huddles, that she’s especially worried about new scurrilous attacks on her family fed to Trump by allies like Roger Stone.


But a major threat facing the under-stress front-runner as she heads into the Sept. 26 showdown on Long Island against Trump isn’t necessarily hidden, and it isn’t necessarily him. While the world waits for word on who will play Trump in debate prep, an equally urgent priority emerging from within Clinton’s team is whether the candidate herself can play someone voters trust, people close to Clinton say.

“We have a ton of work to do,” said a longtime adviser to both Clintons, who, like many of the two dozen other top Democrats interviewed by POLITICO requested anonymity to speak freely.

“Being candid and trustworthy are the two last, big hurdles for her, and the debate is as much about dealing with those as disqualifying Trump,” the person added. “How she deals with it — and her ability to project herself as real and genuine doing it — is an open question … If she gives a canned, evasive and answer I can easily see him pouncing and calling her a robot like Trump and [New Jersey Gov. Chris] Christie did to Marco Rubio” in the disastrous February New Hampshire debate that practically scuttled the Florida senator’s surging campaign.

“In 2016, it’s more difficult for her because of all the trust factors,” said Patti Solis Doyle, Clinton’s 2008 campaign manager. “We had our own challenges, but we didn’t have the issue of the email server, which makes it a much harder climb.”

Bashing Trump may be job one, but the spotlight will be just as bright on Clinton. Her inability to move past the scandals and pseudo-scandals is sapping her support — a Washington Post/ABC poll in Wednesday showed Clinton with the lowest personal approval rating of her 25-year career, with a staggering 56 percent of Americans saying they don’t like her.

One false or cringe-inducing answer on the tender topics of the email scandal and the Clinton Foundation could provide fuel to revive a foundering Trump campaign. It’s happened before. Strategists for Barack Obama and Clinton all agree that her one off-key answer to a seemingly innocuous question in the closing seconds of a November 2007 primary debate was the catalyst for her eventual swoon in the polls.

And that is putting additional pressure on Clinton’s small debate team — which had been almost exclusively focused on attacking the GOP nominee as unfit, unstable and unacceptable — forcing them to grapple with the task of making a stubbornly unlikeable and untrusted candidate more appealing. How they will do that is a matter of debate within her debate prep team.

Clinton Communications Director Jennifer Palmieri called the idea that Clinton had anything to prove a “ridiculous proposition,” adding that the person who “needs to turn the narrative around is Donald Trump, not Hillary Clinton.”

But other members of her team are more worried. Between stops on her epic fundraising blitz this summer, Clinton has been quietly huddling with the two most experienced debate experts in Democratic politics — Ron Klain and Karen Dunn — furiously prepping for either one of the Two Donalds who might show up: the steel-cage slugger or the new, domesticated Trump intent on proving to voters that he can be trusted with nuclear codes.

Over the past two or three weeks, in kitchen table sessions, Dunn, Klain and Clinton’s man-of-many-parts adviser Jake Sullivan (who portrayed Martin O’Malley in primary prep sessions) have been peppering her with Trumpian attacks — including awkward wild-card shots at her family.

The campaign, pushing the idea that the former reality TV star is mentally unstable directly and through surrogates (like top Obama aide David Plouffe, who called Trump “a psychopath” over the weekend), has repeatedly emphasized that the biggest threats posed by Trump are the crazy, deeply personal charges and insults he’ll level at her. But many of the people interviewed for this article, including top campaign officials, privately worry about the sane questions, the ones about her email server and the inside dealings between the State Department and her family’s charitable foundation, believing that they pose the greatest danger.

One of the decisions they have made, according to a person close to the secretive process, is to turn any Trump attacks on the foundation and its finances into a counterattack — blasting Trump for his own lack of charitable giving and leveraged business deals that have left him in debt to Wall Street banks and Chinese financiers.

They are not overly sanguine about turning around perceptions, but do believe presenting an “unfiltered” Clinton, discussing serious issues, rather than acting defensive, will undo some of the reputational damage.

For all the talk of preparing for an unpredictable and outlandish attack from Trump at the first debate later this month (her team has reportedly consulted shrinks and the ghost writer of a Trump book as part of the leaked psy-ops) Clinton is confronting a woman-in-the-mirror reality — a challenge that has bedeviled her during her up-and-down political career.

Steve Elmendorf, a top Clinton fundraiser and veteran D.C. lobbyist close to the Clinton campaign brass in Brooklyn, says the main goal of the effort is “to disqualify Trump,” but conceded that the imperative of shoring up Clinton’s sagging approval numbers was a growing consideration. “Yes, she will have answer the trust and honesty questions,” he added.

Clinton has been mocked by Trump already as a script-addicted, overly prepared debater — in contrast to his own rehearsal style, which ranges from lax to talk-to-me-while-I’m-eating-my-McDonald’s-fries. Despite being surrounded by veteran Clinton haters, led by former New York Mayor Rudy Giuliani, Trump has said he doesn’t plan to stage a mock debate — and thinks that maybe he’ll let daughter Ivanka have a whirl at playing Hillary if he changes his mind.

The former secretary of state, a lawyer to her core, excels at the facts-and-arguments aspect of the exercise, and her command of detail and decision-making is a big asset, as she showed in the earliest debates against a less-prepared Bernie Sanders. But she doesn’t like “surprises,” in the words of one top staffer, and bristled when top aides John Podesta and Howard Wolfson, playing Obama and John Edwards respectively, attacked her harshly in a closed-door session. “She didn’t like that,” said a 2008 Clinton veteran. “She cut down the prep time and limited the number of people who were allowed in the room after that.”

One of her few unscripted triumphs came during the 2000 Senate debate against Republican Rick Lazio, who infamously crossed into her personal space to make a point. She bridled, but held her ground, and Lazio — who was regarded as a lightweight — was quickly dismissed by the media and voters as an un-senatorial bumbler.

Clinton, speaking to me for the “Off Message” podcast remembers being a little taken aback by Lazio’s move — and froze in place less out of fear than because she didn’t want to get in the way of his campaign-killing mistake. “I was more thinking that it would look artificial, it would look kind of phony, and I didn’t want to in any way interfere with a moment that I hoped would reflect badly on him,” she said.

Still, Clinton can’t afford to be just a counterpuncher. Outside the campaign, an increasing number of Democrats, while still confident in Clinton’s ultimate victory, are warning against her waging a Trump-only campaign, and nothing-but-Donald debate. If she can strike the right balance — between trashing Trump and providing mild reassurance to voters leaning, but not sold, on her, the Hofstra University debate could be decisive, they say.

“The debate presents an opportunity — perhaps a mandate — that she display not only command and competence but her character,” says David Axelrod, a longtime adviser to Barack Obama who helped formulate a messaging strategy in 2008 that eroded trust in Clinton and portrayed her as a relic of the past.

“Impeaching Trump, or helping him impeach himself, is one imperative,” he said. “But projecting genuine warmth, humanity and straightforwardness is another.”

For all the flailing and staff changes, Clinton insiders are alarmed at the focused and sustained attacks on her credibility since the new management team of campaign manager Kellyanne Conway, Roger Ailes and Steve Bannon took over in mid-August. After two solid of months of covering Trump’s misfires and campaign turmoil, the media has seized on new revelations about Clinton’s emails (including a fresh batch of previously unreported State Department communications) and details of the cozy relationship between then-Secretary Clinton and top foundation donors, some of them foreign nationals.

“The drop we are seeing now is directly attributable to the emails, the foundation, all the old trust stuff,” said a person close to the Clintons. “That’s why Trump surged around the time of the conventions too. It’s a serious problem, but there’s not a lot we can do about it.”

The person who plays Trump in the mock debates, several people in Clinton’s orbit told POLITICO, has already been chosen, and is an “outsider” — and is already being briefed on the topics that will come up in the murder-board sessions. (It’s not big, blustery Queens Rep. Joe Crowley or Trump-thumping Dallas Mavericks owner Mark Cuban, they say).

The main problem they have been facing, Palmieri says, is figuring out how to parry a politically anesthetized, studiously presidential Trump — the sotto voce statesman who embarked on his polite diplomatic mission to Mexico.

Earlier this week, Clinton shared a bit of her anxiety with an audience at a fundraiser in the Hamptons, “I do not know which Donald Trump will show up. Maybe he'll try to be presidential to convey gravity."

The campaign’s public attitude toward these developments is a studied, shrugging bravado. Clinton insiders recently told POLITICO they planned to respond to Trump’s attacks on her scandals but in a low-key, don’t-dignify-the-question way. “That doesn’t mean no response,” one Clinton aide said late last month, “but a muted one rather than a five-alarm fire.”

Inside the campaign, opinion is far more divided, and while her team is confident in the eventual outcome, there is a debate being waged over how to confront her negatives. So far, Trump, who seems mired at the can’t-win-36-to-40-percent level against Clinton in state and national polls, hasn’t picked up the several point erosion in support the Democratic nominee has suffered since the end of the conventions a month ago — much of the support has leaked into third-party candidates and the none-of-the-above column.

“Clinton needs a strategy for targeting [Libertarian candidate Gary] Johnson & [Green Party hopeful Jill] Stein voters,” Nate Silver, the polling guru who founded fivethirtyeight.com tweeted on Wednesday. “They're clearly drawing more from her side of the ledger now.”

Clinton, a top aide said, “is very confident, very confident in the contrast” between her and Trump, and since 2008 she has often told Obama’s team — jokingly but with edge — that “I only lost one debate against your boss.” Unfortunately for Clinton, that one was huge — the November 2007 rhetorical melee at Philadelphia’s Drexel University where Clinton hedged on the issue of driver’s licenses for immigrants — opening her to attacks of inauthenticity and lack of trustworthiness; Obama rocketed in the polls soon after.

Several senior Democrats with longtime ties to both Clintons cited another “trap” debate. They compared her dilemma to that of Al Gore during the 2000 campaign, when he charged into the fray against an opponent, George W. Bush, he deemed unfit to share the stage with him. “This is eerily similar to the first debate in 2000,” said one longtime adviser to Bill Clinton. “Al want to deliver the knockout punch, and instead people were like, ‘This guy is kind of a dick.’”

And, after all the prep, that’s what it’s about — making American like her, really like her, and making America even more creeped out by Trump than it is already.

Her easiest challenge, ironically, might be on the emails. After months of refusing to offer a mea culpa for setting up a private server and passing around sensitive government emails in a way FBI Director James Comey slammed as “extremely careless,” Clinton has gotten the contrition game down, and has settled on an I-screwed-up stance that she’s likely to repeat over and over during any attack.

The recent crop of stories alleging cronyism and access-peddling at the family foundation may be harder to defend against, in part, because the candidate has thus far left the defense to Bill Clinton and the press team tasked with pushing back. “The campaign has been really reluctant to jump in on the foundation,” one senior Democrat said.

But the ultimate answer to Clinton’s present woes may come from history — and the defense mounted by her husband in 1992 when he faced an arguably more damaging set of revelations — about his serial philandering and Gennifer Flowers’ bombshell allegations that he coerced her to cover up their affair.

Bill Clinton’s stock answer then — “I’ll be alright whatever happens … it’s the American people I’m worried about” — is likely to be repeated, nearly word for word by his wife when she goes face-to-face with a candidate who represents the ultimate cult-of-personality politician.

And Clinton campaign Chairman John Podesta — Bill Clinton’s former White House chief of staff — offered a slogan straight out of the 1990s when I asked him how she’d mount a defense.

“She will fight for the American people and their families,” he said.

