President Donald Trump has had four chiefs of staff, six communications directors, four press secretaries and countless other aides cycling through a stormy White House.
Kellyanne Conway has strategically operated between them, with them and against them to outlast almost everyone.
She spent part of the 2016 cycle lobbing attacks against her future boss before joining his campaign and driving it to a stunning victory. She situated herself as one of Trump’s fiercest fighters in public, one of the most recognizable faces and longest-serving aides defending the president. In a White House known for its burnout and backstabbing, packed with controversies and scandals, Conway was able to outmaneuver a long line of colleagues — skirting the losses and grabbing onto pollster-friendly policy wins she could claim as her own.
“Kellyanne has deftly navigated the treacherous waters of Trumpland that has felled everyone from longtime friends and allies to even family members,” said a former senior administration official. “She’s solidified her place in history as the first female campaign manager to win an election and the president would not be who he is if it wasn’t for her.”
The news of Conway’s departure from the White House was sudden but not entirely surprising to aides. After spending years defending the president from attacks, including those fueled by her husband, a high-profile anti-Trump attorney, Conway announced her departure Sunday night to focus on her family amid a public spectacle involving her teenage daughter.
At the Monday morning senior staff meeting at the White House, she received a round of applause, according to a senior administration official. She later made clear to reporters that, unlike some of her colleagues who faced the equivalent of Trump’s famous “you’re fired” line, she was leaving on her own terms.
“How am I doing? I’m good,” she told a reporter when asked. “I make my own choices.”
At times, she was isolated and sidelined by others in the administration, including Trump’s son-in-law Jared Kushner. But even Kushner brought Conway back into the fold in recent months as other aides fell.
Publicly, Conway was one of Trump’s most skilled knife fighters who knew how to spar against Democrats, the press or anyone who might criticize the president — usually without letting them draw blood in return. Like Trump, she appeared to relish delivering barbs and zingers, but was masterful at managing her relationships with the Washington media, only rarely being exposed.
More than half a dozen former and current administration officials noted that while others have come and gone from the administration with scars to show for their experience with Trump, Conway had the president’s ear and remained in his good graces to the end — weighing in on key issues across the board.
“Her biggest contribution on the policy front is on the opioid battle, but I think that it is limiting her because she was in on almost every policy decision and almost every communications discussion,” said Marc Short, the chief of staff to Vice President Mike Pence. “She was in on almost every consequential thing the administration got done.”
A longtime pollster who worked for Ted Cruz in the 2016 race, Conway earned the president’s loyalty in part for her ability to defend what some viewed as indefensible.
She helped the campaign successfully navigate what was seen as a kiss of death — the surfacing of Trump’s 2005 “Access Hollywood” comments a month before the election — making her the first woman to lead a presidential campaign to victory.
“Trump wouldn’t be in the White House today if it weren’t for Kellyanne publicly defending him after Access Hollywood,” said a former White House official. “If she didn’t do that, it would have been the end of his campaign. He knows without her, he would still be in his office on the 25th floor of Trump Tower right now instead of the Oval Office. That’s why she’s managed to last so long.”
Her willingness to defend anything from Trump was quickly proven in office when she got behind White House press secretary Sean Spicer’s fallacy that Trump’s inauguration had record crowd sizes, coining the now-infamous phrase “alternative facts” to describe his statement.
She herself had been considered for the role of press secretary, but instead joined the administration on her 50th birthday with the title of senior counselor to the president. The role gave her wide latitude — often to the vexation of colleagues around her — to pop into the Oval Office to offer her opinion on everything from policy to communications strategy.
Drawing on her decades as a GOP pollster, she was able to speak to the president’s love of a daily smorgasbord of poll numbers, and she was happy being blunt with the president and sparring with the press, often knowing exactly what buttons to push in televised exchanges with correspondents.
“It’s that kind of toughness that benefits her, not just in articulating the president’s message with a hostile press,” said Trump campaign press secretary Hogan Gidley, who previously worked in the White House. “It allows her to get things done in a town that relishes telling you ‘no.’”
A self-described “happy warrior” for the administration, she appeared to savor her appearances on television spinning some of Trump’s most controversial episodes, while focusing her own work on women, health care and issues impacting blue-collar Americans like the opioid crisis.
Her supporters said Conway was involved in a long list of issues, including Trump’s selection of judges, health care, school choice, and, as a devout Catholic, anti-abortion policies.
Conway “vigorously defended the president at every turn, and she maintained that role as one of the fiercest advocates in every form,” said Short. “Kellyanne was a veteran in a building that often lacked experience and she brought a warrior’s mentality to the building. She was indefatigable.”
Most recently, Conway played a role in the administration’s coronavirus response efforts, sitting in on task force meetings, and she used her experience helping to craft the State of the Union each year to help shape the speakers and direction of this year’s Republican National Convention, at which she will be speaking Wednesday.
Conway’s allies in the White House say her ability to maintain the president’s trust will mark her as a political survivor from the Trump era.
“There may have been others that didn’t like her style or relationship with the president or didn’t like that she was so accessible, and they tried to cut her out or force her out but ultimately those people didn’t last and she did,” a senior administration official said. “It’s a testament to her and her relationship with the Trump family.”
Former Trump aide Cliff Sims, who wrote the blistering tell-all book “Team of Vipers” about his time in the administration, but is now back in the fold, credited Conway for her ability to navigate the tricky waters of the Trump White House.
“If the Trump administration was the Titanic, as many outsiders routinely claimed, then Kellyanne seemed determined to play the role of Unsinkable Molly Brown,” he wrote.