As Hillary Clinton prepared to face the most unconventional candidate of her political career on the debate stage Monday night, her campaign aides engaged in a deep study of Donald Trump's personality to glean insights into how he might act, according to several people familiar with the process.
At a working group session in August, Clinton advisers met with a small group hand-picked by the campaign to help shed light on the Republican nominee. The focus on Trump's personality suggests that Clinton's approach on Monday may be quite different from her strategy in past debates -- and that her campaign expects this event to be unlike any other.
The aides involved in debate prep include her longtime aide Philippe Reines, who has played Trump in mock debate sessions. They conferred for hours with campaign outsiders who were asked to offer advice about Trump’s personality and temperament, according to people familiar with the meeting. The meeting lasted several hours.
Trump’s ghostwriter Tony Schwartz, who has been one of the real estate businessman’s most outspoken critics, was a part of the session. And former UBS Americas CEO Robert Wolf, a friend and ally of President Obama, also participated.
Both men — one who worked closely with Trump to write a book on dealmaking and one who has himself executed hundreds of deals — were tapped to help the campaign understand how a man who has spent most of his life in the business world and who prides himself on being a “deal maker” might behave in a debate setting.
The session represents one of the central parts of Clinton’s debate preparation: to anticipate that Trump will bring an unconventional style to the evening.
Schwartz has spoken repeatedly about his experience working with Trump on his book, “The Art of the Deal.” He has talked openly about his view that Trump’s personality makes him unfit for the presidency.
“He’s stunningly self-absorbed and uninterested in others and he clearly has sociopathic qualities, chief important among them, a lack of conscience,” Schwartz said in an interview. “And therefore he’s undeterred by things that most people would be, such as telling the truth or the potentially harmful consequences of his actions.”
Wolf, who is currently CEO of 32 Advisors and supports Clinton, has participated in presidential debate preparations in the past, including with then-Sen. Barack Obama during the economic crisis in the fall of 2008.
Wolf and Schwartz declined to discuss the meeting specifically or any other interactions with the campaign.
In addition to Reines, the campaign staffers who attended the meeting were Bob Barnett, a lawyer who will play Indiana Gov. Mike Pence in the campaign’s vice presidential debate prep sessions; attorney Karen Dunn; Ron Klain, former chief of staff to Vice President Biden; Christina Reynolds, Clinton’s director of rapid response; Jake Sullivan, a Clinton senior adviser; and Tony Carrk, the campaign’s director of research.
Reines, who has been close to Clinton for years and is known for his combative personality, was on hand to ask questions of the two men.
“He understands how to provoke her or try to provoke her,” said Michael Feldman, a friend of Reines, who was aware that he had been asked to play the role of Trump. “He’s certainly willing to do that, which probably puts him in a very small category of people.
“He’s somebody who’s always been willing to challenge her and tell her just bluntly what he thinks,” added Feldman, who is a founding partner and managing director of the public relations firm, the Glover Park Group.