Voting Station

Madeleine Westerhout

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Personal Assistant

The Resume

    (October 8, 1990- )
    Born in Newport Beach, California
    Interned with Mitt Romney’s presidential campaign (2012)
    Assistant to Republican National Committee Chief of Staff Katie Walsh (2015-17)
    Personal secretary to Donald Trump (2017-19)
    Had titles of ‘executive assistant’ and ‘special assistant to the president’
    Named Director of Oval Office Operations (February 2, 2019)
    Fired after it was revealed that she had discussed Trump's relations with his family with reporters at an off-the-record dinner (August 29, 2019)

Why she might be annoying:

    She cried when Trump was elected – and not tears of joy.
    She reportedly irritated several White House officials and cabinet secretaries by trying to expand her role into a ‘de facto chief of staff.’
    Ironically, she had called an earlier leak of Trump’s schedule ‘a disgraceful breach of trust.’
    She reportedly boasted of having a better relationship with Trump than his daughters did.
    She claimed Trump disliked being photographed with his daughter Tiffany because he considers her fat.

Why she might not be annoying:

    During the post-election transition period, she became known as ‘elevator girl’ and ‘greeter girl’ because she was frequently photographed escorting guests through the lobby of Trump Tower.
    Until the gaffe that got her fired, she kept a low profile.
    An administration official noted, ‘This was an off-the-record dinner and the media blatantly violated that agreement.’
    Although he said her comments about his children were ‘a little bit hurtful,’ Trump called her ‘a good person’ who did her job well.
    Heck, while tweeting about her firing, Trump made far more negative comments about ‘disgusting and foul mouthed Omarosa’ than her.

Credit: C. Fishel


Featured in the following Annoying Collections:

Year In Review:

    In 2023, Out of 17 Votes: 58.82% Annoying
    In 2022, Out of 6 Votes: 50.0% Annoying
    In 2021, Out of 15 Votes: 66.67% Annoying
    In 2020, Out of 6 Votes: 66.67% Annoying
    In 2019, Out of 21 Votes: 52.38% Annoying