Clinton preps for Trump’s Lewinsky attack Democrat’s team searches for a close ally willing to dredge up the most awkward, painful accusations against the candidate.

It’s one of the most uncomfortable and important jobs in Democratic politics: trying to embarrass the woman who could be the next president.

The person picked to be Hillary Clinton's sparring partner in her upcoming debate prep sessions is expected to confront her about the death of Vincent Foster, label her a rapist's enabler, and invoke the personally painful memories of Monica Lewinsky and Gennifer Flowers.


Clinton’s team is beginning its preparation ahead of the first general election debate, scheduled for Sept. 26 at Hofstra University. And one of the key components of that prep, campaign allies said, is finding a person who can stand in as Donald Trump during mock debates and launch personal attacks on the former secretary of state that will make the real Trump look tame by comparison.

“It needs to be someone who is naturally smart, glib and utterly irreverent,” said Democratic strategist Bob Shrum, who oversaw debate prep for Al Gore and John Kerry. “You can’t learn to be utterly irreverent.”

Even so, out-Trumping Trump to prepare Clinton is an inherently awkward enterprise, one which is expected to unfold only in front of a small group of trusted aides. Clinton allies are comparing the confidentiality surrounding the tricky upcoming prep sessions to that of a closed film set when actors are shooting a nude scene.

“You can't put it beyond Trump that Monica Lewinsky will play a role in this debate,” said Greg Craig, President Barack Obama’s former White House counsel, who played George W. Bush in Kerry’s 2004 debate prep, and John McCain in prep sessions against Obama in 2008. “She's got to be prepared to deal with the [Clinton] Foundation and Wall Street and super PACs and all of that. They need to be less focused on dealing with his policy proposals and more on dealing with the unexpected. He’s going to be in attack mode, probably the whole time.”

Added Gene Sperling, former director of the National Economic Council, who has been involved in prep sessions for Bill Clinton, Gore and Kerry: “Debate prep, in general, is a weird thing. It offers the possibility for passive aggressiveness against your boss.”

This year in particular, it's a job that nobody close to Clinton is particularly eager to take on. “You have to start off by saying, ‘I want to thank the American people, especially Monica and Gennifer Flowers,” anticipated a top Clinton ally with close ties to the campaign. “Nobody who is a friend of hers is going to want to say that in debate prep.”

But challenging Clinton to prepare her for Trump is also one of the most crucial roles in the general election. The first debate is widely expected to overshadow the conventions, the Olympics and the Super Bowl in terms of television ratings. “It is rare that a candidate can win the election at a debate,” said Craig, “but it's quite frequent that one can lose the election during a debate.”

For weeks, Clinton has been fielding jesting offers from donors at fundraisers: “if you need someone to play Donald Trump in debate prep,” they joke, “you know who to call.” The topic comes up so often she has remarked on it to her Brooklyn-based campaign staffers.

Self-made billionaire Mark Cuban, who endorsed Clinton last month, told POLITICO he would be “happy to do it” but noted that no one had yet asked.

But Democrats said he might have the swagger to avoid being too deferential to Clinton. Rep. Joe Crowley, a New Yorker with a large presence, could perhaps more accurately channel Trump’s Queens heritage, other Clinton allies said. Other potential Trump stand-ins discussed include James Carville, a naturally irreverent character who is trusted by the Clintons; Sen. Al Franken of Minnesota, a longtime Clinton ally with an actor’s rearing; and Ron Klain, the former Joe Biden aide who is helping to run Clinton’s general-election debate prep and is already part of her leak-free inner circle.

Former Pennsylvania Gov. Ed Rendell joked that he is “probably one of the only ones who says things bordering on the outrageous like Trump does" but that he was not angling for the job.

Playing the opponent requires hours of studying game tape of every response Trump has given in a debate or an interview, in order to anticipate exactly what he will say. Such preparation has been easier in past elections, depending on the candidate. George W. Bush was a highly scripted candidate who memorized stock answers to most questions. "He had a presentation that he gave all over the country that he went to almost reflexively,” said Craig, who played him in prep sessions against Kerry. “With Trump, it’s going to be different.”

“It’s a complicated debate prep,” agreed Shrum. “The Clinton challenge is to prepare for the crazy Trump who will probably show up, some kind of toned-down Trump, and the somewhere-in-between Trump.” Trump could spend 90 minutes berating Clinton for helping to found ISIS, Democrats said, or he could turn on the moderator and the media so that Clinton simply becomes a bystander rather than a participant. He could even devote real time to preparation and surprise Clinton by his substance on the issues.

“He’ll say anything,” added Rendell. “It’s almost impossible to be totally prepared.”

If Trump remains on message, Clinton allies expect him to attack her personal email use at the State Department, the overlapping orbits of the Clinton Foundation and the Clinton-led State Department, and Obama’s foreign policy legacy. They expect him to call her “crooked” and focus on her gaffe that she “short-circuited” when she recently made misleading statements about her email use.

But campaigning in Connecticut over the weekend, Trump also taunted the Clintons by noting he was happy Lewinsky had “kept the dress,” noting, “it shows who the hell they are.” It was the latest warning shot to Democrats of how awkward things need to get in prep sessions to make sure Clinton is psychologically prepared for what could be thrown in her face.

Clinton’s debate prep group is being led by senior policy adviser Jake Sullivan. Klain and attorney Karen Dunn are serving as the lead outside advisers. Clinton's longtime attorney Robert Barnett is also involved. A source close to the campaign said the work has already started in earnest, and that every day there’s an hour or so devoted to boning up on the briefing books about Trump. The source described Clinton as “very confident” about taking on Trump and looking to steer the debate toward specific proposals. A Clinton campaign spokesman declined to comment about debate prep.

Preparation for the first general-election debate is always one of the most grueling parts of the fall campaign: The candidate typically drops off the trail to camp out in a battleground state with a small team of advisers for intense sessions and full simulations on a set built to look just like the stage.

The person playing the opponent is typically assigned his own staffers to prep him — and during "debate camp" will keep to himself even between mock sessions in order not to break the adversarial tension necessary for a successful prep.

“You are there to kick their ass,” recalled Democratic strategist Paul Begala, who played George W. Bush in debate prep against Gore. “You immerse yourself in the style and the substance.”

Begala said it’s not so much about arriving with the self-tanner and comb-over wig necessary to impersonate Trump as it is about nailing his speech patterns and likely lines of attacks. “You don’t want to spend too much time trying to perfect the affections,” Begala said. “If he’s prone to interruptions, you need to mimic that. If he’s prone to repetition, you need to mimic that. You’ve done your job as the stand-in if, during the debate, the opponent repeats everything you already said in prep.”

Finding the right person to play the opponent is also a calculation about how to get the candidate fully focused. Bill Clinton and Obama were both unwilling to devote any attention to debate prep. “He had not been willing during the primaries to put in the time necessary to get ready — and it showed,” Craig recalled of Obama’s 2008 debate prep. “The biggest open question going into the presidential debate prep was whether he was going to be willing and able to put in the time and have the discipline to get ready.”

In 1996, Bill Clinton’s aides recruited former Sen. George Mitchell to play Bob Dole, mainly because they needed someone who Clinton wanted to impress to get him to actually engage in a serious way. “We worried that he might be a little cocky debating Dole,” recalled Sperling. “Mitchell was pretty near his equal. We knew he was going to work harder just because he wasn’t going to enjoy being in debate camp where he was being bested.”

“You should have seen George Mitchell thrash Bill Clinton in 1996,” Begala recalled. “And it worked; Bill Clinton was the only president I’ve seen in my lifetime who did well in the first debate.”

Hillary Clinton, in contrast, “is disciplined,” Sperling said. “You don’t have to get George Mitchell to make sure she’s going to work hard.”

But even when aides have successfully anticipated for the candidate 90 percent of the action that unfolds on the debate stage, it’s the one unplanned exchange that can derail an otherwise flawless performance. In 2004, Craig said, “we were nine out of 10 when it came to predicting the questions. But the final question of the debate — when CBS moderator Bob Schieffer asked the candidates, “Do you believe homosexuality is a choice?” — elicited an unpracticed answer that undid all the other work. Kerry invoked the sexuality of Mary Cheney, the gay daughter of the vice president, in a response that was considered out of bounds and backfired on him.

“That's the fear,” said Craig. “Hillary Clinton may be very successful at presenting her economic plan, or talking about how we destroy ISIS, but then if there's one mistake or one exchange that is in some respect embarrassing, it could dominate all of the coverage.”

The stakes will be even higher for Trump, who has been sinking in all national and battleground polls. The debate stage will likely provide him with his last chance to look like he can manage a world stage and change voters’ perceptions about him. A Trump spokeswoman declined to comment about the candidate’s prep routine.