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 as 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. “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 Obama’s former White House counsel who played George W. Bush in John Kerry’s 2004 debate prep, and John McCain in prep sessions against Barack Obama in 2008. “She’s got to be prepared to deal with the 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, the 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 was “happy to do it,” but noted that no one had yet asked.
But Democrats said he might have the 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, a longtime Clinton ally with an actor’s rearing, and Ron Klain, the former Biden aide who is running 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. That 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.
Read Full Story At Politico