Back in 2017, fresh faced 26-year-old Madeleine Westerhout landed her dream job as President Donald Trump’s EA. All of a sudden she had access to (probably) the most powerful man in the world. She was literally walking the corridors of power and taking flights on Airforce One. But in 2019 that world came crashing to a halt when she was
fired from her dream job, accused of sharing details of the Trump family and Oval Office with reporters during an off -the-record dinner. Here Executive PA does a deep dive into Madeleine’s story.
Confidentiality is, of course, a cornerstone of an EA’s job. In fact, did you know the original term for a personal assistant was ‘secretary’, which comes from the Latin word “secretarius’ – it means a ‘confidential officer’ or a ‘keeper of secrets’?
So, perhaps Madeline should have known better when she was invited out for a boozy dinner with a bunch of nosey journalists. But Shakespeare’s words there’s ‘many a slip betwixt cup and lip’, especially when you’re fed copious amounts of white wine. And Madeline sure did slip! After one glass too many she effectively said her relationship with Trump was better than that of his daughters, and added that he disliked being photographed with his daughter Tiffany because he thought she was overweight. We’ll never know the exact context of the conversation. But the news hounds had sniffed out a headline opportunity and the pack ran with it.
An overnight author
As a consequence she was sacked. Shortly after this she penned a book, Off the Record: My Dream Job at the White House, How I Lost It, and What I Learned, which describes her initial view of Donald Trump before she met him (it wasn’t favourable), how she got the job and a ‘warts and all’ account of her fall from grace.
Although a high achiever, Westerhout was arguably not ready to take on such a big role at the time. So, it would be understandable for the book written so soon after the event to be full of recriminations and criticisms of her boss; particularly given his combative nature and his regular negative media attention. It would have been easy for her to join in without damaging her long-term career. In-fact, it could have helped her.
The book however, is full of praise for her former employer. She describes how her opinion, formed by what she had read in the media, changed from one of mild distaste to admiration almost as soon as she started to interact with him. Trump expected results but gave her authority and space to get on with her job. He included her in his trusted circle and recognised her achievements. What more could an EA ask for?
Most telling, the book describes how he handled the controversy at the time and her dismissal, which understandably he could have taken personally because his children had been at the centre of her comments. As soon as the story went public, he made a statement that Westerhout had broken a condition of employment and would not continue in the job – but he sweetened the bitter pill: “I think it was automatic,” he said. “I don’t say ‘fire’ or ‘not fire.’ I really think she had a bad night. I think it was unfortunate. She said she was drinking.”
He is said to have spoken with a contrite Westerhout over the phone after the event and accepted her apology. And, some time after the dismissal, she was contacted by one of Trump’s inner circle to connect her with potential employers. Such textbook people management skills would not usually be associated with Trump. However, it paid dividends in terms of PR – and subsequent support from Westerhout.
Madeleine’s book is full of examples of generosity and whilst she acknowledges that Trump has used vulgar language in the past, she points out that these comments were made in a different time and present standards should not be used to judge them.
Where is she now?
So, Madeleine Westerhout recovered from a very public humiliation. She is now vice president and chief of staff to the Chairman at American Global Strategies and, recently, testified at Trump’s first criminal trial.
He was charged with 34 counts of fraud related to alleged to hush money paid to Stormy Daniels, an actress in adult films, before the 2016 election. He pleaded not guilty, arguing that the allegations are not criminal.
His former EA cried as she testified and was full of praise for the President and his wife: “I believe they have a relationship of mutual respect. I just found their relationship really special, and he really cares a lot about her opinion.” She added that Trump “never once made me feel like I didn’t belong there” and was “a really good boss”.
She also said one of her reasons for writing the book was to “share with the American people that the man that I got to know… I don’t think he’s treated fairly and I wanted to tell that story.”
This article is part of a feature that appeared in the Winter issue of Executive PA Magazine. The second part Dealing with a “Bad Boss” – words with Michelle Gibbings is a video interview and transcript, between EA Naomi Spinks and workplace and leadership expert Michelle Gibbings.
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