Kellyanne Conway Takes on Toughest Role Yet: Trump Whisperer

The first woman to manage a Republican presidential campaign has her work cut out for her.

Donald Trump Stays the Same Amid Campaign Shakeup

Strategist and pollster Kellyanne Conway has been in the business of politics for more than two decades, but she may have taken on her toughest job yet: Trump whisperer.

With her promotion to campaign manager, Conway will now travel at Donald Trump’s side until Election Day, charged with helping him reduce the self-inflicted wounds that do major damage to his image, and loading him up with facts and ideas before he takes the microphone.

Kellyanne Conway speaks during an interview on Bloomberg TV in New York on July 5, 2016.
Kellyanne Conway speaks during an interview on Bloomberg TV in New York on July 5, 2016.
Photographer: Chris Goodney/Bloomberg

Previous handlers—including ex-campaign manager Corey Lewandowski, campaign chairman Paul Manafort, and Trump’s own children—have tried to guide him. The question remains whether Conway will be successful, but as a pollster, she has an immediate connection with her poll-obsessed boss, colleagues said. 

“She gets along with Donald Trump very well. They understand each other. She knows how to get ideas to him without making him feel defensive or pushing her away,” said longtime friend Gary Bauer, who ran for president in 2000.

Making her job more difficult, however, Trump admits he doesn’t like to be told he can’t do or say something. Trump has also denounced pollsters—“I don’t want to waste money on pollsters. I don’t want to be unreal. I want to be me. I have to be me,” he said on NBC's Meet the Press a year ago—but with about 80 days to go and everything on the line, he’s now leaning on them. It’s a sign of how dire the race has become, as Democratic nominee Hillary Clinton widens her lead in polls in crucial battleground states.

“Kellyanne will be a better communicator than Trump is. She’s that good,” said fellow pollster Frank Luntz, who employed Conway until she broke off and opened her own firm in 1995.

Conway, a 49-year-old movement conservative from New York, is the first woman to manage a Republican presidential campaign. She has long specialized in working with women candidates and attracting female voters. She has the ear of Trump’s most potent female surrogate and trusted adviser, his daughter Ivanka. 

Conway isn't the only person in her family who has worked to take down the Clintons. Her husband, George T. Conway III, a lawyer at Wachtell, Lipton, Rosen & Katz, was behind some of the most bitter lawsuits against Bill Clinton in the 1990s and stories that were promoted via the Drudge Report.

The staff changes on Wednesday brought more conservative fire power into play. Steve Bannon, executive chairman of the website Breitbart News, was drafted to take over the campaign as CEO, while the strategist who was in charge for months, Manafort, remains in place with different duties. Conway was promoted from senior adviser to campaign manager. 

“She’s the perfect balance to Steve Bannon,” Luntz said. “Bannon is to tell Trump what Trump wants to hear. Kellyanne is going to tell Trump what Trump needs to hear. That’s what makes her different.”

But some of Conway’s colleagues said it won’t be easy for her. The paradox of Trump is that he’s best when he’s being outspoken. But when the campaign is going badly, it’s also because Trump is being outspoken, as when he said a federal judge couldn’t make impartial decisions because of his Mexican heritage, or disparaged a father whose son died in the Iraq war, or made a joke that seemed to imply “Second Amendment people” should take violent action against Clinton, they said. 

“Kellyanne’s challenge is going to be a big one in the sense that she’s going to have to keep up with somebody who’s incredibly passionate and incredibly smart and wants to win,” said David Bossie, of the advocacy group Citizens United, who has been friends with her for 20 years and uses her as his organization’s pollster.

Bauer said Conway will understand that “there’s only one alpha dog” when Trump is in the room. “Kellyanne is smart enough to know if you want to influence his thinking, it’s by using your wisdom and wit to convince him, rather than confront him,” he said.

Trump is “an aggressive figure” whom some women dislike, Bauer said, but Conway will give Trump suggestions for appealing to female voters, including “security moms” concerned about terrorism.

Conway has already sought to add a new dynamic to the campaign. She arrived through the front doors of Trump Tower Wednesday afternoon and took questions from reporters before spending the day with Trump in briefings and crafting advertising for their first round of TV ads.

She nicknamed Bannon, Manafort, adviser Rick Gates, and herself “the core four” on the team.

“We’re going to divide the responsibilities according to our best uses,” she said. “We have to cover our airwaves, our ground game. It’s great if they have me out on the plane or out on the TV circuit. It’s really great to have Steve here at HQ handling all those different pieces along with Rick and with Paul.”

In Conway, Trump gets a political operative with deep ties to Tea Party politics, a wide network of conservative influencers, and some establishment politicians, including Republican vice-presidential nominee Mike Pence. Conway was Pence’s pollster for both of his gubernatorial campaigns in Indiana. She was a Newt Gingrich adviser when the “Contract for America” was being put together.

Conway is skilled at presenting complex data in a way that’s easily digestible, said GOP strategist Phil Musser, who is familiar with her work on state and congressional races. She “can be very forceful and strong and direct when she needs to be,” he said.

And she has a talent for sharp criticism of the Clintons, her associates said.

“She’s got smarts,” said Robert Vane, who was a spokesman for Pence’s re-election campaign, “and she’s got stones.”

—With assistance from Kevin Cirilli, Terrence Dopp, and Mark Niquette.

Watch Next: Kellyanne Conway Defends Trump's 2nd Amendment Remarks (Aug. 10) 

Trump Adviser Conway Defends 2nd Amendment Remarks
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