Vice President Kamala Harris has never met or spoken with former President Donald J. Trump, but the woman running her debate preparations has spent a lot of time thinking about how to respond to what Republican nominees say during an onstage clash.
That outside Harris adviser, Karen L. Dunn, a high-powered Washington lawyer, has trained Democratic presidential and vice-presidential candidates for debates in every election since 2008.
She is described by candidates she has coached and other people who have worked with her as a skilled handler of high-ego politicians. By all accounts, she possesses the rare ability to tell them what they are doing wrong and how to fix it — and how to inject humor and humanity to sell themselves to voters watching the debate.
“It’s a combination of tough love,” Hillary Clinton, whom Ms. Dunn helped prepare for presidential debates in 2008 and 2016, said in an interview on Thursday. “She’s unafraid to say, ‘That’s not going to work’ or ‘That doesn’t make sense’ or ‘You can do better.’ But she also offers encouragement, like, ‘Look, I think you’re on the right track here’ and ‘You just need to do more of that.’”
The emergence of Ms. Dunn as the leader of Ms. Harris’s debate team comes at a critical moment in both the presidential race and Ms. Dunn’s professional life.
When she is not preparing top Democrats for debates — in addition to her four previous cycles of involvement at the presidential and vice-presidential level, she has worked with Senators Mark Warner of Virginia and Cory Booker of New Jersey — Ms. Dunn is a top lawyer for some of America’s leading technology firms.
The beginning of next week is something of a collision course for her.
On Monday, Ms. Dunn is due in federal court in Alexandria, Va., where she is expected to deliver Google’s opening statement in the federal government’s second antitrust case against the tech giant, which could result in the breakup of a famed American company. The next night in Philadelphia, Ms. Dunn’s latest debate student — Ms. Harris — will face off against Mr. Trump in the biggest night of the vice president’s political career so far.
The two roles reflect Ms. Dunn’s ascension to the top echelons of Washington’s political and legal communities — and show how much the country’s business and government interests can be intertwined.
When she represents Google in court starting on Monday, Ms. Dunn will sit across from Justice Department lawyers who work for Attorney General Merrick B. Garland, who helped officiate her wedding in 2009 and, of course, is the senior law enforcement officer in the federal government in which Ms. Harris is the vice president.
“If these were legal cases, she would be ethically barred from doing what she’s doing,” said Matt Stoller, the director of research at the American Economic Liberties Project, a progressive nonprofit group that studies monopolies. “It’s clear that you can’t serve both sides.”
Steven Lubet, an emeritus professor of legal ethics at Northwestern University’s law school, said Ms. Dunn was well within her rights to be opposed to the government in court and helping Ms. Harris for the debate.
“Lawyers in private practice volunteer on political campaigns all the time,” Professor Lubet said. “There’s no conflict between coaching debate prep and representing a client in a case opposed to the government.”
Ms. Dunn, 48, began her career in politics working as a legislative correspondent on Capitol Hill for Representative Nita Lowey of New York. In 1999, she was hired as the second employee on Mrs. Clinton’s 2000 Senate campaign. She rose to communications director and remained in Mrs. Clinton’s Senate office, working alongside her during and after the Sept. 11 terrorist attacks.
She briefly left politics to attend Yale Law School and worked as a law clerk for Mr. Garland and then for Justice Stephen G. Breyer. By 2008, she was back working for Mrs. Clinton on her presidential campaign, and after Barack Obama won the Democratic nomination that year, she helped with his debate preparations. When Mr. Obama won the election, she took a job in the White House Counsel’s Office. She later worked as a federal prosecutor in Virginia.
“She is someone who as a lawyer sweats the details, but she has an ability in her communications work to see the big picture, and that’s really a rare quality,” Mrs. Clinton said. “If you’re preparing a client for court, you have to be able to get the most positive performance out of your client, and it’s the same for a debate.”
Ms. Dunn returned to help with Mr. Obama’s 2012 debate preparations and then worked with Mrs. Clinton again before the debates during the 2016 primary and general election — preparing her for the three face-offs with Mr. Trump that fall. She then led Ms. Harris’s sessions for her 2020 debate with Vice President Mike Pence.
In addition to working for Google, Ms. Dunn has represented Uber and Apple. She also helped prepare the Amazon founder Jeff Bezos when he was called to testify before Congress.
In 2021, Ms. Dunn won a landmark lawsuit in Virginia in which organizers of the 2017 far-right rally in Charlottesville were found liable for injuries to counterprotesters. She won more than $25 million in damages and was prominently featured in an HBO documentary about the case.
Ms. Dunn, who is volunteering her time to the Harris campaign, was made available for this article, described her theories of a successful political debate in an interview with The New York Times in July 2019.
At that time, two dozen Democratic candidates were competing in crowded presidential primary debates broken up into multiple nights. Ms. Dunn, who was not aligned with a candidate in the primary, said the goal for each contender was to create a winning moment, preferably at the expense of someone else.
“In order to have a moment in a debate, you have to actually engage with another person on the stage in a way that is in some regard a challenge to that other person,” she said. “If somebody comes after you and you counterpunch effectively, you can win that moment. If you’re the so-called front-runner and somebody punches you and you counterpunch and win the exchange, then you own that moment.”
People who have participated in debate prep with Ms. Dunn described her as not just meticulous about the briefing materials presented to the candidate and campaign aides but also obsessive about avoiding leaks from inside the sessions.
Ms. Dunn does not circulate debate materials electronically, insisting on printed materials unique to each prep session. She then requires each participant to destroy or return the briefing books at the end.
It was Ms. Dunn who suggested that Mrs. Clinton bring up Mr. Trump’s insult about a beauty pageant contestant’s weight and remind the audience of the woman’s humanity.
“He called this woman ‘Miss Piggy,’” Mrs. Clinton said. “Then he called her ‘Miss Housekeeping,’ because she was Latina. Donald, she has a name.”
Mr. Trump, rattled, tried to interrupt. “Where did you find this?” he said.
Mrs. Clinton pressed on.
“Her name is Alicia Machado, and she has become a U.S. citizen, and you can bet she’s going to vote this November,” she said, creating what was at the time a signature debate moment.
Mr. Warner, the Virginia senator who employed Ms. Dunn to prepare him for debates in his 2014 and 2020 campaigns, said that while some of his other advisers could identify where he was falling short, Ms. Dunn was able to go a step further and offer concrete suggestions about how to improve his performance.
“In debate prep, in many ways, you’re at your most vulnerable,” Mr. Warner said. “I’ve had other people try to help, and if I’m in a big-time debate or big-time presentation, there’s nobody I’d want more on my side than Karen Dunn.”
In Pittsburgh, Ms. Dunn is leading a Harris debate team that includes Rohini Kosoglu, a former policy director who was a chief of staff to Ms. Harris in the Senate; Tony West, Ms. Harris’s brother-in-law; Sean Clegg, a lead strategist on Ms. Harris’s 2020 presidential campaign; Brian Fallon, a top communications aide for the vice president; Sheila Nix, the campaign’s chief of staff; Lorraine Voles, the chief of staff in the vice president’s office; David Plouffe, a senior adviser to the campaign; and Cedric Richmond, the former congressman who is advising Ms. Harris’s campaign.
Philippe Reines, a Democratic operative who helped prepare Mrs. Clinton for her 2016 debates against Mr. Trump, has returned with his Trump costume to portray the former president.
The team is expected to hold several 90-minute dress rehearsals, complete with lecterns, television lighting and questions posed by a rotating team standing in for David Muir and Linsey Davis, the ABC News anchors moderating Tuesday’s debate. Those sessions will be filmed, with Ms. Dunn and others reviewing the footage to show Ms. Harris where she can improve.
Ron Klain, who has prepped several Democratic presidential nominees beginning with Bill Clinton in 1992 and ending with Joseph R. Biden Jr., has worked alongside Ms. Dunn in several election cycles.
Mr. Klain described one of her strengths as being comfortable enough to scrap the candidate’s initial approach completely. This happened when Mr. Obama faltered in his first debate against Mitt Romney in 2012. After that appearance, Mr. Klain and Ms. Dunn encouraged Mr. Obama to speak faster and in a less professorial tone.
“So I need to be hammy,” Mr. Obama, who never quite warmed to the idea of striking a casual tone while in office, told the pair. Ms. Dunn then coined a phrase that persuaded him to speak with less formality and more familiarity: “Ham-and-cheese delivery,” she replied.
The post Harris’s Debate Tutor: a Lawyer Unafraid of Telling Politicians Hard Truths appeared first on New York Times.