Trump Weighs Aggressive Tactics Against Clinton in First Debate

(Bloomberg) -- Hillary Clinton and Donald Trump have been locked in a fierce election battle for months, but tens of millions of Americans will compare their presidential bona fides side-by-side anew on Monday.

The first of three debates promises to be a national sensation, contrasting two vastly different New Yorkers who are recognized around the world. Clinton, known for her extensive experience in government, is more comfortable discussing substantive issues than pitching her candidacy, and Trump excels as a self-promoter and an unsparing critic of his adversaries.

The Democratic nominee is preparing for an unpredictable opponent who “hangs back a lot, picks his moments” and “may be aggressive,” according to communications director Jennifer Palmieri. Her challenge: driving home her message to voters regardless of what he does, Palmieri said. 

The Republican nominee is being advised by some in his orbit to put his rival on defense by questioning her judgment, intelligence, and accomplishments, as well as by confronting her over controversies surrounding the Clinton Foundation, her private e-mail server, and her paid Wall Street speeches, and by accusing Clinton and her husband of exploiting the Haiti earthquake for personal gain.

But his advisers are also wary of him going too far and coming across as a bully. Underscoring their concern about striking the right balance, the Trump campaign emailed a debate prep survey to supporters. Among the questions: "Do you think Trump should refer to Hillary as 'Crooked Hillary' on stage?"

The debate at Hofstra University in New York comes six weeks before the Nov. 8 election, as Trump has closed the gap nationally and in several battleground states, with Clinton retaining an edge in the Electoral College.

“It’s going to be a high-stakes drama,” said Peter Hart, a leading Democratic pollster. “In an hour and a half or two, opinions get suspended and people look at the candidates, on large measure, afresh. There are a certain number of open windows for people to look and decide what they’re feeling.”

“Voters who say ‘I worry that I can't relate to Hillary’ will get an opportunity to see her. Voters who wonder if Donald Trump has the temperament or the knowledge to be president—they get to see that,“ he said.

How They Are Preparing

In a Fox News interview Tuesday, Trump campaign manager Kellyanne Conway cited a recent forum on military issues hosted by NBC's Matt Lauer as a “very good preview” for what to expect from Trump during the debate. She said his answers to questions will be “concise and confident” in contrast to Clinton’s “lengthy” and “lawyerly” responses.

Clinton told donors in the Hamptons last month she’s unsure which Trump will show up to the debate: one who will try to be presidential and convey “gravity,” or one hurling insults to “score some points.”

“You have to assume, well, he might approach the debate this way or he may approach it that way and he may be aggressive or he may lay back,” Palmieri said. “That’s hard to game out necessarily.”

Trump has been practicing for weeks while traveling with his top advisers. This week alone, he spent time with Newt Gingrich, Rudy Giuliani, Michael Flynn, and Ben Carson, asking each of them between campaign events for their advice on potential questions for the debates, according to people familiar with his plans. 

Trump aides have indicated that he isn’t practicing with mock debate sessions where someone plays Clinton. He’s campaigning through Thursday, and on Sunday he has reserved an entire day to prepare for the debate inside Trump Tower, according to people familiar with his plans.

Thus far, Clinton aides have declined to say who is playing Trump in her rehearsals or to say when and where she’s preparing. She was at home in Chappaqua, New York, all day Tuesday and—after a day trip to Florida on Wednesday—she has no campaign events scheduled through the debate.

Clinton is working with the team that helped her gear up for Democratic primary debates: Karen Dunn, Ron Klain, Bob Barnett, John Podesta, Joel Benenson, Jake Sullivan, and Palmieri. Barnett is standing in for Republican vice-presidential nominee Mike Pence in Democratic running mate Tim Kaine’s preparations. Tony Schwartz, co-author of Trump’s most successful book, The Art of the Deal, is also assisting.

Clinton has hinted that if Trump appears more restrained on stage, she’ll remind voters of the real-estate developer and TV personality’s history of inflammatory comments and controversies. “He’s trying to somehow convince people to forget everything he’s said and done, and I don’t think that he’s going to get away with that,” Clinton said in an interview that aired Monday on The Tonight Show.

Robby Mook, Clinton’s campaign manager, told CNN on Wednesday she’s “going to have to spend some time probably correcting the record” during the debate because Trump “doesn't often tell the truth.”

But she’s also bracing for a more confrontational Trump to take the stage.

“I’m going to do my very best to communicate as clearly and fearlessly as I can in the face of the insults and the attacks and the bullying and bigotry that we’ve seen coming from my opponent. You know, I can take it,” Clinton said Tuesday on The Steve Harvey Morning Show.

‘Likable Enough’

Clinton, facing criticism for avoiding press conferences for over 270 days, has begun to do gaggles with reporters regularly in recent weeks. Meanwhile Trump, who used to do regular press conferences in the first half of 2016, has mostly avoided adversarial reporters lately in favor of regular interviews on the relatively friendly Fox News.

David Kochel, a Republican strategist and former top adviser to Jeb Bush's presidential campaign, said a blustery Trump “maximizes base turnout and keeps his people fired up” but “doesn't grow his electorate.”

“Hillary's negatives are high enough that he could win over Trump-doubting Republicans and independents by showing a presidential bearing, similar to his appearance in Mexico City,” he said.

“Hillary’s main goal is to be natural, authentic, and show humor without a script—be ‘likable enough.’ She’s a better debater than she gets credit for, but this debate will be far more about style than substance, because of Trump’s outsized presence on the stage,” Kochel said. “I would also have her prepped to needle at Trump’s wildly overstated wealth, as that seems to be the one thing that most easily flusters him.”

In the Republican primary, Trump demonstrated a knack for relentlessly branding his opponents—using labels such as “low-energy” Bush, “little” Marco Rubio, and “lyin’” Ted Cruz—in ways that stuck and paid off for him. He frequently calls his Democratic rival “crooked Hillary.”

Clinton, meanwhile, has focused heavily on criticizing Trump rather than making a positive case for herself. She's fluent in topics sure to come up in the debate and the lines of attack on her record she can expect from Trump, because they were part of the debates during the 2008 Democratic primary race. Those include her vote to authorize the 2003 invasion of Iraq, her shifting positions on trade, and questions about her honesty.

In four one-on-one debates with President Barack Obama in 2008—and 17 others that included other candidates—Clinton showed her ability to go on offense and make it personal. She was able, at times, to rattle Obama enough to bring a candidate known for his cool demeanor to the brink of losing his temper.

Steve Schale, who managed Obama’s 2008 campaign in Florida, said the debate on Monday will be critical in establishing the contours of the race in its final weeks.

“The only thing that matters is that first debate,” he said. “If Trump succeeds at passing the presidential test—which I think is a huge lift, particularly standing toe to toe with Secretary Clinton—then we will absolutely be in a fight to the end. But if he falls short, the question won't be whether she will win, but by what margin.”

—With assistance from Jennifer Epstein, Kevin Cirilli, Joshua Green, Margaret Talev, and Jennifer Jacobs.

To contact the author of this story: Sahil Kapur in Washington at skapur39@bloomberg.net.

To contact the editor responsible for this story: Mike Nizza at mnizza3@bloomberg.net, David Knowles