Can Kellyanne Conway Save Trump From Himself?

In January 2013, dismayed and defeated after Barack Obama had won
his second term and Democrats had maintained the Senate, House
Republicans–intact, but fraying–gathered at the Kingsmill Resort near historic Williamsburg. A GOP pollster familiar to many of them rose and addressed her mostly male audience. Stop, she urged them, talking about rape.

It’s a “four-letter word,” pollster Kellyanne Conway said, according to reports from the time.

It wasn’t that Conway wanted the party to change its position on abortion. But as an adviser to Rep. Todd Akin (R-MO) in his Senate race she had seen first-hand how he had derailed the entire party with his “legitimate rape” comments, and Conway was determined to get Republican men to think about the way they talked.

Now she may be doing it again as the female political pro closest to Republican presidential nominee Donald Trump, a candidate who has built a reputation as being almost impossible to get through to.

Conway, 49, has connections to some of the conservative movement’s most salient organizations and figures, from Susan B. Anthony’s List to Freedom Works to Gov. Mike Pence to Newt Gingrich. Her rise in the Trump campaign came after she led a super PAC that supported Sen. Ted Cruz (R-TX), and she is making some conservatives who have doubted Trump’s conservative bonafides feel more at ease.

Kellyanne Conway speaks with Rep. Steve King (R-IA) at conference in Washington, D.C.

“If he is ready to listen to her, it says to me that this is the most significant indicator that he is shifting,” said Marjorie Dannenfelser, the president of Susan B. Anthony’s List who has been friends with and worked alongside Conway for years. “The shift to Kellyanne is a shift to try to figure out how to win.”

Trump’s campaign seems to be in free fall at the moment as states like Arizona and Georgia, which never were intended to be in play in the 2016 election, are in Clinton’s grasp. Trump is driving up deficits with college-educated whites and married women – constituencies Mitt Romney won handedly– and dozens of Republican strategists are calling on the Republican National Committee to pull the plug on Trump and reallocate resources to down ballot races as soon as possible.

Kellyanne Conway speaks about getting more women in politics at Politico Event

While Trump’s hiring of Steve Bannon, the conspiracy-churning Breitbart
News chairman to be his campaign CEO last week troubled many Republicans,
Conway’s promotion was a sign of progress for those still holding out hope.

“She is a happy warrior. She is a small government conservative, and she will not be pushed around,” said Adam Brandon, president and CEO of FreedomWorks who has worked with Conway for years. “You cannot underestimate the impact this can have on major donors.”

Conway got her start in 1988 working for Ronald Reagan’s pollster on how the Republican Party could better attract women voters. In 1995 she struck out on her own and started the Polling Company/Women Trend, which she still runs.

Advisers and campaign operatives who have worked with her describe her as tough, yet professional. Someone who tells you directly what you might not want to hear, but does it with decorum.

“There are some people out there who come up with polls that are good news. You don’t hire Kellyanne to do polling for you if that is what you are looking for,” said Gary Bauer, a friend of Conway’s, conservative activist and former president of the Family Research Council. “She has become a trusted adviser and someone who understands the best way to work with Trump.”

In her interview with the Washington Post from July, Conway said herself that she had discovered the best way to break through the noise with Trump was not to demand that he change, but give him choices. She used an example of how she once convinced her daughter to change her turquoise outfit for Memorial Day by laying out truer blue alternatives.

“Minutes later,” she told the Post, “she came out in one of those shades.”

But Conway will only be able to do so much. Before she joined Trump’s campaign, when she was working to elect Cruz, she was very clear about Trump’s problems with women.

Conway told the Daily Beast that when women “hear Donald Trump in his own words, they can make a clear-headed decision about, ‘Will the real Donald Trump please stand up?'”

Since she came on board, Conway has attempted to make the case that Trump is not who some women may believe he is.

“This is a man who just promoted a woman without using the word,” Conway told MSNBC. “I think you should judge people by their actions not just their words on a political campaign trail.”

What Conway won’t do, colleagues say, is fundamentally overhaul the identity of a candidate. Instead, she softens around the edges.

“She always wanted Governor Pence to be exactly who he was,” said Robert Vane who has served as communications director for Pence’s gubernatorial re-election campaign and sat in on strategy meetings with Conway when she was working for him. “Kellyanne was certainly polished and certainly professional, but she really wanted to keep Governor Pence comfortable in his own skin.”

But keeping Trump Trump is a gamble.

This is a candidate who has called women dogs, attacked Heidi Cruz’s appearance, said women who have abortions should be punished and remarked that Fox News host Megyn Kelly had “blood coming out of her wherever” during a Republican debate.

Ken Blackwell, who has worked with Conway as both a politician and as an activist, said he believes that Conway has picked the job because she views this election as a “binary choice.” He believes instead of throwing in the towel on Trump like so many strategists, Conway is sticking around because she believes he is a better choice and wants to do everything she can to help the party in the election.

Kellyanne Conway speaks at Iowa Freedom Summit during the GOP Primary

“Her optimism is a direct understanding that she can make a contribution,” Blackwell said. “She doesn’t sugar coat things. She won’t give you a bucket of BS. I think if she thought this was already a fait accompli she wouldn’t waste her time or the time of friends she is going to be recruiting to help.”

After two campaign shakeups in two months, it it is unclear if Conway– even with her expertise and conservative bonafides– can become the campaign manager Trump will finally listen to. In the end Conway’s success may not hinge on her abilities at all, but on the willingness of Trump finally to open up his ears and take advice.

“If Trump wants to be president, he is going start to listen to people who have competencies and experiences that go beyond his bucket of competencies and experiences,” Blackwell said. “If not, he will be the victim of his own short sightedness.”

On Thursday night, there was a small change from Trump on a stage in North Carolina.

“Sometimes, in the heat of debate and speaking on a multitude of issues, you don’t choose the right words or you say the wrong thing. I have done that,” Trump said. “And believe it or not, I regret it.”

When asked if the expression of regret was her idea, Conway denied it.

“It was not me. That’s all Donald Trump,” she replied. “He’s the candidate here, I’m not.”