Off the Record

My Dream Job at the White House, How I Lost It, and What I Learned


By Madeleine Westerhout

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Madeleine Westerhout, the former “gatekeeper” of the Trump White House, writes about her relationship with the president, and tells the story of the terrible mistake that led to her losing her job.

From the first day President Trump stepped into the White House, Madeleine Westerhout was by his side, first as his executive assistant, then as the Director of Oval Office Operations. From her desk outside the Oval, she saw everyone who came in to see the president. She placed his phone calls, and was in the room for several historic moments. During her time working with President Trump at the White House, Camp David, Mar a Lago, and Bedminster, she grew to love her job and admire the president.

Then, in an unguarded moment during a dinner with reporters, she made a terrible mistake.

In Off the Record, Westerhout tells the full story of this dinner for the first time, revealing the circumstances that led to her fateful mistake. She also writes about her relationship with President Trump — all the lessons she learned working with him, and why she believes he is a much different man than the one the media portrays every day. Westerhout describes President Trump as a kind and generous boss who continues to be a great leader for our country.



The Dinner

The answer was no.

The answer was always no whenever I was asked to engage with reporters, and it didn’t matter what the context was.

So naturally when I was invited to join a group of them for dinner one night in August 2019, I said no again. I had every reason to be wary.

After all, what good could possibly come of it?

Reporters are… reporters. They are not your friends. They care about the story, not you.

Especially the reporters who cover the Trump White House, where I worked, a White House that has been under siege from the Fourth Estate since Donald Trump took the oath of office as president. Heck, since November 2016, when the candidate the media was pulling for, Hillary Rodham Clinton, lost.

Here we are, four years later, and many Democrats still argue that Hillary should be president because she collected the most popular votes. Nonsense. A candidate wins the election by collecting the most electoral votes, and that’s what Donald Trump did.

To be fair, I have no interest in indicting the entire profession. I’ve met my share of journalists who approach every assignment with an open mind, and don’t allow their bias to slant their reporting. I understand why the president gets angry with them—there is a ton of fake news—though I don’t entirely agree with him that the mainstream media are the “Enemy of the People.”

Too many reporters, however, search only for evidence to back up the premise they begin with, and if finding it requires them to rely on anonymous sources or ignore irrefutable facts on the opposite side, so be it. The way they see it, any tactics, no matter how unethical, can be justified if they might lead to the downfall of the man they despise.

No president, at least in modern times, has been treated with more disrespect than Donald Trump.

Reporters claim that all they are interested in is telling the truth. Give me a break. They write their story first, act as judge and jury, and worry about the truth later. When they make a mistake, which is too often the case, good luck getting them to admit it.

The story is on the front page, impossible to miss. The correction is buried on an inside page—if it’s there at all.

I can’t tell you how many times I’d be sitting at my desk right outside the Oval Office and see “breaking news” about the president or somebody else in the administration on the screen and think, Oh, my God, I can’t believe this is happening, only to find out from others in the West Wing that the report was a total fabrication.

Yet if someone like myself, who worked in the West Wing, could be misled that easily, what about the people outside of Washington who wouldn’t be able to separate fact from fiction?

What bothered me more than anything was the constant stories that the president was angry the whole day, berating his aides. I had been with him from practically the moment he stepped into the Oval Office, and I can assure you that wasn’t the case. Where the media came up with lies like that was beyond me.

So you can understand why I might not have been interested in having dinner with those “truth tellers.”

Besides, I was enjoying a much-needed rest on a gorgeous Saturday afternoon, lounging by the pool at the president’s golf club in Bedminster, New Jersey, roughly an hour from New York. Bedminster had been our home for the prior nine days. I wrote some emails, splashed around in the pool, soaked up the summer sun, and downed a few drinks.

The president always urged the staff to take advantage of the facilities at his properties once our work was done. We didn’t need much convincing.

I was in a tremendous mood. Our trip in mid-August 2019 couldn’t have gone any more smoothly.

The president was happy. The first lady was happy. The senior staff was happy. As his executive assistant—think Mrs. Landingham from The West Wing—I took a great deal of pride in what we accomplished. I was aware of how easily it could have gone the other way.

Donald Trump, you see, never looks forward to being away from the White House for more than a couple of days. He is frustrated by the image of him that has been spread by the press—shocking, I know—that he doesn’t work very hard. Add that to its long list of lies. He works extremely hard. I’ll go as far as to say that he has more energy than everyone else in the West Wing. We could barely keep up with him.

The president often starts his workday about 6:00 a.m.—he typically sleeps for only four or five hours—and some nights, he doesn’t get off the phone until around midnight. He believes in returning everyone’s call, and I mean everyone. I can’t imagine there has been anyone in that office who has made himself more available.

Furthermore, he adores everything about the White House. Which is why it is outrageous that people suggest he doesn’t enjoy being president. He enjoys it very much.

This is someone who didn’t need the job, who took it on only because he loves his country and believed he was the right man to turn things around. He could have gone on as the celebrity he had been for much of his adult life, admired for the most part, and no one would have given it a second thought.

Instead, he ran for president, the most demanding job in the world, against overwhelming odds and put his legacy on the line.

The history of the institution itself is never lost on him. When he had a guest in the Oval Office, he often told me, “Madeleine, get the picture of John-John.” He was referring to the famous photo from the early 1960s of President John F. Kennedy’s two-year-old son, John-John, playing under the Resolute Desk.

“This is the same desk,” President Trump would proceed to tell his guest. “Come, let’s take a picture behind it.”

On more than a few occasions, when some of the staff were staying a little later than usual, the president would usher us into the Oval Office. “Look around,” he’d tell us. “Look where we are. How incredible is this? We are standing in the Oval Office!”

I can’t overstate how much moments like that meant to me. My colleagues and I would get so wrapped up in our day-to-day responsibilities, we would forget where we were and how essential our work was. Incredibly, it was our boss, the president of the United States, who had to be the one to remind us.

He always appreciated how fortunate he was to be a part of history. I will never forget the first time the president rode on Marine One, the presidential helicopter.

From my office overlooking the Rose Garden, I watched him as he watched the helicopter land and then as he made his way from the Oval Office and across the South Lawn to Marine One.

He stopped in front of the marine who was standing guard by the helicopter and gave the most respectful salute. Donald Trump had been in many helicopters—and private planes, for that matter—but that look of reverence in his eyes told me this time was different.

For the August trip to Bedminster, we needed to be as persuasive as ever in order to get him to agree to it. He didn’t want to go for long, certainly not ten days. In the summer of 2017, when the West Wing underwent a much-needed renovation, he had gone to his club for two weeks and been destroyed by the media. They had suggested he was merely taking a vacation, and nothing could have been further from the truth. I’m not even sure the word vacation is in Donald Trump’s vocabulary.

Besides, every president gets out of Washington in August for a week or longer. The city all but shuts down. Congress is out of session, and the weather is just miserable. President Barack Obama used to go to Martha’s Vineyard, while George W. Bush took off for his ranch in Crawford, Texas.

When President Trump returned from those two weeks in 2017, he told us, “I’m never going away for that long again.”

He wasn’t kidding. Even when he went on foreign trips, he wanted the schedule to be as condensed as possible. Often he would leave late so he could fly through the night and land in the morning in time for him to start his workday. It was grueling for the staff, but the president didn’t want to be gone one moment longer than necessary.

“I will sleep on the plane,” he used to say.

This time, we felt he had no choice.

“Sir, you have to go to Bedminster,” we told him. “They’re working on the air-conditioning system in the Oval and updating a couple of things in the residence, so you physically will not be able to work or live in the White House. Mrs. Trump will be in Bedminster. Barron [their thirteen-year-old son] will be there, and so will Ivanka, Jared [Kushner, Ivanka’s husband], and their kids. We will make sure it’s a productive week, that you will do as much or as little as you want. It will go by very quickly, we promise you.”

Mission accomplished.

Of course, once we got him to Bedminster, there was no guarantee that he would want to stay there. It wouldn’t have surprised any of us if, halfway through the ten days, he had told us, “I’m wasting my time here, and I’m getting killed by the press. Why can’t we leave for DC tomorrow so I can get back to work?”

It never got to that point, thank goodness, and that was because he kept busy, catching up on calls and paperwork, while also receiving briefings from his advisors.

He also took advantage of some sorely needed time off. I worked with the club’s golf pro to set up foursomes for the president with friends, members of Congress, and prominent businessmen. He prefers to play with golfers at his level or better.

One night, the president enjoyed a family dinner, and on the Friday before we left, he dined with Mrs. Trump and Tim Cook, the CEO of Apple. The three had a wonderful time.

By the eve of our return to the capital, slated for Sunday morning, August 18, he seemed as content as ever and more confident, too. I’m not suggesting that he wasn’t in complete control from the start. It was just that like others who had occupied that office before him, with each day that went by, each crisis he faced, for better or worse, he grew more and more into the role.

For me, it was an honor to watch up close as he further grasped the subtleties of such a formidable challenge. As he relaxed, the staff could relax. As with any job, we felt secure only when the boss was pleased.

Much to be proud of happened in those ten days. Take the events we held in Pennsylvania and New Hampshire.

Unless you are in the arena and observe how excited people get to see Donald Trump in person, you can’t possibly appreciate what a rock star he is. Television gives you a glimpse of that, but it does not come close to capturing the remarkable atmosphere. I’ve never been to a rock concert with more energy than a Trump rally.

His supporters routinely show up at the arena the night before; many stand for hours and hours, waiting for their hero to arrive. I normally watched the speech from the staff viewing area, close to the stage, and never failed to recognize how fortunate I was.

Such a rally is most likely the only time these people will ever see the president up close. I saw him up close, day after day, for more than two and a half years.

At the podium for about ninety minutes, he isn’t a phony, like countless others in public office. He relates to everybody in the building as if they were lifelong friends. He does not talk at them; he talks to them, much as President Franklin Delano Roosevelt did during those famous fireside chats on the radio in the 1930s and ’40s.

It’s precisely what many people are yearning for, as they struggle to get by in a country that seems to have forgotten they exist. The president doesn’t forget, not for a second. He makes them feel that they matter, and to know there is somebody in the White House fighting for them raises their spirits like nothing else. Other politicians have let them down, over and over. Sure, they said all the right things about increasing our wages, protecting our borders, improving our health care, and so on. But, in the end, those politicians have had more in common with one another than with the citizens they are supposed to serve. That goes for Republicans as well as Democrats.

Without question, no one gets more out of the rallies than President Donald J. Trump. No wonder he feels so energized whenever he is on the road. He is reminded of all the good work he is doing for this country that the press never bothers to report on, and for which the Democrats never give him credit.

Take prison reform, something the Democrats have been talking about forever. The president got behind the issue, leading to shorter sentences and job training for prisoners, and only a handful of Democrats praised him for the vital role he played. I’m not implying he did it to receive the credit, although it sure would be nice.

When he’s speaking at those rallies and sees how the people react to him, he remembers: This is why I’m the president. For these people right here.

People tend to forget how much of the country voted for him. Every so often, when he hosted CEOs whose companies focused on issues that affected mostly rural areas or members of Congress from Middle America, he would call out from the Oval Office, “Madeleine, bring in the map.”

The map broke down, state by state, county by county, who had voted for him and who had voted for Hillary Clinton. The East and West Coasts were mostly blue. The rest of the country was filled with red.

Like Vanna White in Wheel of Fortune, I would walk into the Oval Office proudly holding the map.

“Look at all that red,” he’d say.

At times the staff grew discouraged by the barrage of attacks from the media and also needed to be reminded of who we served. It’s easy to lose sight of that while sipping a cocktail in a swanky DC hotel. Like it or not, we’re also part of the elite.

The people at the Trump rallies do not care about what the New York Times or the Washington Post says they should care about: the Russia investigation, the president’s income taxes—you name it. They care about feeding their families, paying their bills, and keeping their country safe.

As for the events we held in August, they were like many other events during the 2016 campaign and ever since, Donald Trump being… Donald Trump.

In Pennsylvania, at a petrochemical complex still under construction about thirty miles from Pittsburgh, he touched on so many topics that it was hard to keep track: the Paris Agreement on climate change, the Green New Deal, immigration, Iran, China—even the Academy Awards, which had been held way back in February.

No one, the president said, watches the Oscars anymore because of the celebrities “disrespecting the people in this room.”


Two days later, at the rally in Manchester, New Hampshire, he went off against “radical socialism” and brought up one of its chief advocates, Massachusetts senator Elizabeth Warren.

Once Donald Trump gets rolling, it’s impossible to stop him, and why would you even bother? 2020, here we come!

The rest of the August trip was just as productive, starting with two fund-raisers in the Hamptons. The first was held at the home of the real estate developer Stephen Ross, who is 95 percent owner of the Miami Dolphins football team; the second at a 17,000-square-foot mansion belonging to another billionaire developer and Republican donor.

The program was the same for both. The president began in a photo line with guests and then conducted a roundtable with twenty or so of the major donors. It was supposed to go for roughly twenty minutes. As usual, it didn’t. The man likes to talk. Which is totally fine. He is the president of the United States. He can talk as long as he wants. Each donor contributed $100,000, perhaps more. They deserved their money’s worth.

Speaking of the upcoming election, we also had a political meeting at Bedminster. We held one every month or so to get an update on how we stood in each state. So far, so good, no matter what the polls were saying about this Democrat or that Democrat claiming the advantage in a potential one-on-one showdown. Remember, the pollsters in 2016 said that Hillary Clinton would be the next president.

In earlier discussions, the president had told us he would drop by this particular meeting for only a couple of minutes. He ended up staying for three hours.

That shocked no one, and as usual, he didn’t just sit there and listen; he posed one probing question after another. It’s remarkable how involved he gets on intricate political matters.

“How many staff members do we have in this state?”

“How much money have we raised here?”

“Should we put more resources in this part of the country?”

The media have constantly speculated on who the president and his team were hoping to run against. Truth was, he wavered. One week, he would say, “Please let it be Bernie [Sanders]. I would love to go against him in a debate.” Another week, he would be praying to take on former vice president Joe Biden or Senator Warren.

Whoever it would turn out to be, the feeling in the West Wing was the same: we got this.

Sitting by the pool that afternoon, I felt vindicated for having pushed as hard as I had to make it to Bedminster in the first place.

There were some on the White House staff who didn’t feel I should be there. As a matter of fact, they were never in favor of my traveling with the president. Some of them had worked their entire careers to acquire such access, and now, out of nowhere, came a twenty-six-year-old assistant with no experience in government—and she gets to spend as much time with the president as we do? We can’t allow that to happen.

Those staff members didn’t say it in so many words, but I’m certain the fact that I am a woman made them resent me even further. The people who tried over and over to hold me back—and I am not just talking about going on trips—were men. That can’t be a coincidence.

Most threatening to them was how close the president and I seemed to be. He trusted me, and there aren’t many people he trusts. His wife. His family. His closest friends. Maybe a handful of others, such as Hope Hicks, who was then director of strategic communications, and Dan Scavino, who was director of social media, but that’s about it.

Over time I became privy to information about Donald Trump and his family that other staffers were not. I never planned it that way, it just happened. I think—and I hope I’m not being presumptuous—that the president saw me almost as another daughter. I definitely saw him as a father figure. He was very kind and thoughtful and took care of me, just like my own dad.

“Where’s Madeleine?” the president asked several times when he was on Air Force One or Marine One. “Why isn’t she with us?”

Access, it may come as no surprise, meant everything in the Trump White House, and I’m sure it was not much different in previous administrations. The closer you were to the president physically, and the more time you spent with him, the more important you were—or were perceived to be. That explains why many staffers complained on a regular basis if they weren’t in the spot they thought matched their position.

On occasion, I’m ashamed to admit, that included me. If somebody with significantly less status, perhaps a junior staffer from the the Eisenhower Executive Office Building (EEOB) sat in the same area as I did on Air Force One, I would feel frustrated.

Of course, when a woman complained, it wasn’t treated with the same urgency as when a man did. The women who work in the White House, the members of this particular boys’ club believe, should be grateful for anything they can get.

“Why are you making a big deal out of this?” a male staffer asked me on more than one occasion. “You’re on the trip, aren’t you? You’re on Air Force One!” He never would have said that to a man.

Thank goodness there was one person who saw absolutely nothing wrong with a young woman gaining influence: Donald Trump. Goes against everything you’ve heard about him, doesn’t it?

It happens to be true. The president respects women more than any other man I have worked for. Hope Hicks. Kellyanne Conway. Sarah Sanders. Stephanie Grisham. Nikki Haley. Elaine Chao. The list goes on and on. And on a more personal level, needless to say, the first lady and Ivanka. Each woman is powerful and talented.

One night at Bedminster, I called the president to run something by him, and he mentioned that he and the first lady, having a movie night, had just been talking about me. The film was Breakfast at Tiffany’s, one of my favorites.

“Melania said you remind her of Audrey Hepburn,” the president said.

The iconic film, which was released in the fall of 1961 and based on a novel by Truman Capote, starred Hepburn and George Peppard.

“Honey,” the president joked with her, “that might very well be the nicest compliment you’ve ever given.”

I was in such good spirits that when Hogan Gidley, the White House principal deputy press secretary, who had mentioned the dinner earlier, asked me again if I wanted to join him and the reporters, I surprised myself. I said, “Sure, why not?”

It was Saturday night, and I had nothing else to do. I had given some thought to attending a bachelorette party for a friend in Montauk, a village on Long Island, but decided that it was too far away and I wouldn’t get back in time to leave with everyone for DC the next morning.

The fact that I had been drinking throughout the day and my defenses were down also had something to do with my changing my mind. I never would have agreed to a dinner with reporters if I had been completely sober.

No doubt I shouldn’t have been drinking in the first place. Especially after what I knew about the damage alcohol can cause.

I had two upsetting experiences in my past that were due to excessive drinking.

At a party in high school, I kissed a guy whose girlfriend was in another room. Someone saw us, and everyone at the party found out. The girlfriend and her friends held it against me for the rest of high school even though the guy had been the one to initiate it. What made it worse was that it was my first kiss and will always be my first kiss.

You think that’s embarrassing? That was nothing compared to what happened in college. I was kicked out of my sorority, Alpha Delta Pi, for drinking when I was an intern at our national headquarters in Atlanta, Georgia. I can’t pretend that I didn’t know the rules. I was the president of my chapter at the College of Charleston. I knew all the rules. Nevertheless, just like that, something dear to me was taken away for good.

Yet there I was with a few drinks in my system, agreeing to spend time with people who were, essentially, strangers. Dinner, without question, would include more alcohol.

Those types of get-togethers are actually fairly common on the road. The press sees such a dinner as a chance to get better acquainted with members of the White House staff, and to ensure that it’s a social and not official occasion, it’s made clear at the outset that everything is off the record.

Hogan and I left for dinner around seven. I was nervous. I wasn’t sure if the reporters would approve of me. What if I bored them? What if they didn’t like me? It was too late, though, to back out now.

Besides, I felt comfortable around Hogan, who, although about ten years older, was one of my better friends in the West Wing. He was superb at promoting the president and his agenda but also kind and sensitive. I knew he would have my back. What could go wrong?

After a roughly twenty-minute drive, we arrived at the Embassy Suites, where most of the media were staying, and met our companions for the evening: Philip Rucker of the Washington Post, Andrew Restuccia of the Wall Street Journal, Jennifer Jacobs of Bloomberg, and Steve Holland of Reuters.

When Hogan and I walked in, I thanked the reporters for allowing me to join them. We then made our way to the Liberty Grille, the hotel restaurant.

The only person I knew even vaguely was Steve, who I thought was a fair reporter and who had always been warm toward me. I had been Steve’s guest a few months before at the Gridiron Club dinner in DC, which has long been one of the most important gatherings of the year. The others I recognized from the daily press pools. The most I had ever said to them was something like “The president is ready for you.” Engaging with the media any further than that was out of the question.

The Liberty Grille wasn’t fancy. We took a rounded booth toward the back of the room. I sat at the end.

The six of us hadn’t been seated for more than a few minutes when the reporters suggested we order some wine and asked whether I liked white or red. I said I preferred white but would be fine with whatever they wanted. We ordered one bottle of white and one bottle of red, and the drinks kept flowing.

Soon afterward, Hogan left to do a live hit on Judge Jeanine Pirro’s show on Fox, which he could do from the hotel. He had told me about the interview earlier, so I’d known that he would be leaving. I figured he would be gone for twenty minutes at the most. I should have known better. Judge Jeanine, who is incredibly passionate in her support for the president, has a good rapport with Hogan and sometimes keeps him on air for longer than scheduled.

He wound up being gone for more than an hour.

I should have been more nervous without him there. I wasn’t. Quite the opposite; I felt comfortable, and I thought I was in total control. For a change, I was the center of attention, not Hogan, and as much as I thought of myself as someone who preferred to be out of the spotlight, a part of me relished it. It comes from a need for approval and a desire to please others, which goes back as long as I can remember and may have something to do with my parents divorcing when I was only four years old. I always wanted to be the perfect daughter, the perfect student, the perfect everything.

I don’t remember how many glasses of Sauvignon Blanc I drank, but it did its job. It didn’t make matters better that I had had those drinks by the pool and hadn’t eaten anything since breakfast.

Everyone thought that Hogan would be back soon, so we waited to order dinner. We waited, and waited—and kept drinking. Meanwhile, the reporters started to ask questions, one after another. They had me, the president’s executive assistant, all to themselves. Better yet, they had somebody they knew never spoke to the press. North Korea, Iran, the border controversy, the tax bill; they did not ask anything about those issues. They had plenty of sources for policy matters.

No, they were looking for something juicy concerning the president and the lives of the first family, the kind of palace intrigue they couldn’t find anywhere else.

“How do you think Barron is adjusting to living in the White House?”

“What is the president’s relationship with Tiffany like?”


On Sale
Aug 11, 2020
Page Count
272 pages
Center Street

Madeleine Westerhout

About the Author

Madeleine Westerhout was executive assistant to President Donald Trump from 2017 to 2019, and the Director of Oval Office Operations at the White House from February to August 2019.

Learn more about this author