All featured products are independently selected by our editors. However, when you buy something through our retail links, Vanity Fair may earn an affiliate commission.
The inner circle of Trumpworld was not always a pretty picture. Too often, it was a portrait of venality, stubbornness, and selfishness. We leaked. We schemed. We backstabbed. Some of us told ourselves it was all done in the service of a higher calling—to protect the president, to deliver for the people. But usually it was for ourselves. Most of us came to Washington convinced of the justice of our cause and the righteousness of our principles, certain that our moral compasses were true. But proximity to power changes that. Donald Trump changes that. The once-clear lines—between right and wrong, good and evil, light and darkness—were eroded, until only a faint wrinkle remained.
A particular case in point involves Kellyanne Conway, who had the title of Trump’s 2016 campaign manager. (Though it was really Jared Kushner, if anyone, who was actually in charge.) As counselor to the president, Kellyanne managed to land a job with no fixed responsibilities. “What exactly does Kellyanne do?” was a question people asked all the time. So she was able to continue being the president’s pit bull on TV—a job that never goes out of fashion in Trumpworld—and otherwise just dabble in areas that piqued her interest. She would later focus her efforts on the opioid crisis and veterans’ issues, but early on she was content—very content—to sit back, go on TV, and let rivals eat one another alive. And she was predictably resentful of both Ivanka and Jared’s immovable status in Trump’s orbit.
As I watched Kellyanne in operation over our time in the White House, my view of her sharpened. It became hard to look long at her without getting the sense that she was a cartoon villain brought to life. Her agenda—which was her survival over all others, including the president—became more and more transparent. Once you figured that out, everything about her seemed so calculated; every statement, even a seemingly innocuous one, seemed poll-tested by a focus group that existed inside her mind. She seemed to be perennially cloaked in an invisible fur coat, casting an all-knowing smile, as if she’d collected 98 Dalmatians with only 3 more to go.
I’m not sure the president ever fully understood that about Kellyanne. But what he clearly shared with her was a love of media attention. Unlike most human beings, Trump’s greatest fear wasn’t death or failure or loss. It was obscurity. If he was noticed, he mattered. And he didn’t care much if the attention was good or bad, as long as it wasn’t indifferent. Mentions in the press had long been his oxygen. Another Page Six scoop, another breath. A Time magazine cover, a shot of adrenaline. He spent his adult life keeping the brand going, whatever it took. He couldn’t just own a nice hotel, but the most beautiful hotel ever built. He couldn’t just have a difficult divorce, but the most sensational ever to hit the tabloids. He couldn’t just have a popular TV show; it had to be the most highly rated in history. He couldn’t be a good president; he’d have to be as great—greater, even—than Lincoln.
Trump sincerely held most members of the media in low regard—that wasn’t just for show. But what he didn’t like to admit was that he also craved their approval. And nothing was more a focus of his attention in this regard than The New York Times. It was his hometown paper, after all. During a dinner with evangelical leaders in the Blue Room, Trump named the exact number of occasions he had been on the front page of the Times during his career as a businessman. It was only a handful. “Now, I’m on there almost every day,” he observed, though usually not in the way he would have liked. He added, with a mix of pride and irritation, that Ivanka, who was also in the room, still got better coverage in the Times than he did.
Like many presidents, he was obsessed with White House staffers who leaked against him—and was always on a quest to figure out a way to unmask them. On one memorable occasion, the president got a prominent White House reporter on the phone who had written a story that quoted anonymous staff members. “Who gave you this story?” Trump asked playfully. “I’d just be curious to know who told you this.”
The reporter laughed somewhat nervously, saying they obviously could not reveal their sources. Leaning over the phone in the Oval Office, arms crossed in front of him with his elbows sitting on the Resolute Desk, Trump tried to cut a deal. “Well, I guess that’s fine,” he replied. “But, of course, you know I could give you so much better stories—so much better.” After a little more unsuccessful coaxing, Trump relented. The reporter hung up without a hot scoop from “a source close to the president.”
His somewhat-playful attempted bribe was unsuccessful that day, but Trump never halted his effort to uncover the leakers in his midst. It was also a favorite parlor game among staff in the West Wing to guess who the unnamed White House officials were in various stories. But one day, by sheer accident, I didn’t have to guess anymore.
In May 2017, the hosts of MSNBC’s Morning Joe appeared on-air to accuse Kellyanne of being two-faced when it came to Donald Trump. Mika Brzezinski claimed that when Kellyanne came on their show during the campaign, she would lavish Trump with praise, and then “the camera would be turned off, the microphone would be taken off, and she would say, ‘Blech, I need to take a shower,’ because she disliked her candidate so much.” Joe Scarborough asserted that Kellyanne had only taken the Trump gig because it would pay off financially. And they both said they had decided to no longer book her on the show because she lacked credibility.
Kellyanne had developed pretty thick skin, and normally she would let this kind of stuff go. So I was a little surprised when she called me upstairs to her office to discuss issuing a response. I assumed this was because she feared Trump would believe the charges, which might threaten her plum White House position of doing whatever it was she wanted whenever she felt like it.
Kellyanne’s office was one of the largest in the West Wing. On the top floor, above Steve Bannon and Kushner’s offices below, it was about twice as long as it was wide. On the south end of the room, where her desk sat, she had the most valuable commodity in the West Wing: two fairly large, square external windows. On the opposite end of the room, she had a small conference table that could comfortably seat six. In between, there was a sitting area with a couch and two chairs positioned on opposite sides of an oval coffee table. The office had been set up this same way when Valerie Jarrett occupied it during the Obama years. Just outside her door, in a tiny reception area, sat her executive assistant, who handled her calendar, and her body man, who shadowed her every move and catered to her needs.
I had not brought my work laptop upstairs with me when she called, so Kellyanne pointed over to her personal MacBook sitting on the conference table on the other side of the room. “Just use that and type something up for me,” she said.
I sat down and started slowly pecking out a statement. While working in the White House, I found that I’d grown so accustomed to writing in Trump’s voice that writing for other people had become somewhat harder than it normally would have been. I was already getting off to a slow start, but I was also getting distracted by the nonstop stream of iMessages popping up on the screen. At that point, personal phones had not yet been banned in the West Wing, so Kellyanne was sitting at her desk texting away. And since her iMessage account was tied to both her phone and her laptop, which she must not have even considered, I could inadvertently see every conversation she was having.
Over the course of 20 minutes or so, she was having simultaneous conversations with no fewer than a half-dozen reporters, most of them from outlets the White House frequently trashed for publishing “fake news.” Journalists from The New York Times, The Washington Post, CNN, Politico, and Bloomberg were all popping up on the screen. And these weren’t policy conversations, or attempts to fend off attacks on the president. As I sat there trying to type, she bashed Jared Kushner, Reince Priebus, Steve Bannon, and Sean Spicer, all by name. (“The real leakers, past and present, get much more positive press than I do. While it’s rare, I prefer to knife people from the front, so they see it coming,” Conway said in a statement shortly after publication. According to a source familiar with the situation, the statement was drafted in consultation with her husband, George Conway. Subsequently, George Conway has denied involvement with the statement on Twitter. A White House aide close to Kellyanne Conway insisted that George Conway was not involved in this statement, but did contribute to the statement submitted to Morning Joe. )
She also recounted private conversations she’d had with the president, during which, at least in her telling, she’d convinced him to see things her way, which she said was a challenge when you’re dealing with someone so unpredictable and unrestrained. She wasn’t totally trashing the president, at least as the Morning Joe crew described it, but she definitely wasn’t painting him in the most favorable light. She was talking about him like a child she had to set straight. I was sitting there, watching this, totally bewildered. I was supposed to be writing a statement, defending her against accusations that she had done almost exactly what I was watching her do that very moment.
When Fox & Friends co-host Abby Huntsman later asked Kellyanne about allegations that she was the “No. 1 leaker” in the administration, she sidestepped the question, only saying that “leakers get great press,” and adding that “one day, Abby, I will have my say.”
From what I saw on her computer, she was having her say all day long. Kellyanne was playing a double game—putting a foot in both worlds—telling Trump and his supporters on Fox one thing, while bad-mouthing them to the “mainstream” media in private. It didn’t hurt matters with the latter group that her husband, George, was an increasingly frequent critic of the president on Twitter. If the Trump administration was the Titanic, as many outsiders routinely claimed, then Kellyanne seemed determined to play the role of the Unsinkable Molly Brown. She wasn’t going to go down with this ship.
I suspect that posterity will look back on this bizarre time in history as if we were living in the pages of a Dickens novel. It was the age of wisdom, it was the age of foolishness. Some of us on both sides of that blurry divide were young, wide-eyed, and seeing the real world for the first time. Others were battle-weary, watching with great cynicism the twisting of the American experiment. Those of us who were there were part of a unique moment in time when the greatest nation on earth wrestled with its better angels and its nagging demons. We will hold tight to the triumphs, lose sleep over the failures, and perhaps shed tears over what could have been. Some of us will be proud of what we did. Others will be ashamed and never speak of it again. Some will remember this as the best work we ever did. Others will wish it could all be deleted from the record.
Lincoln famously had his Team of Rivals. Trump had his Team of Vipers. We served. We fought. We brought our egos. We brought our personal agendas and vendettas. We were ruthless. And some of us, I assume, were good people.
This article is adapted from Team of Vipers by Cliff Sims. Copyright (c) 2019 by the author and reprinted by permission of St. Martin’s Press.
This article has been updated.
