A Former Trump Assistant Gives a Glimpse of What Loyalty Means to the Former POTUS

NEW YORK, NEW YORK - MAY 09: Madeleine Westerhout, a former Trump executive assistant, departs Manhattan Criminal Court on May 09, 2024 in New York City. Stormy Daniels, whose alleged sexual encounter with Trump is a... NEW YORK, NEW YORK - MAY 09: Madeleine Westerhout, a former Trump executive assistant, departs Manhattan Criminal Court on May 09, 2024 in New York City. Stormy Daniels, whose alleged sexual encounter with Trump is at the center of this case, concluded her testimony in former U.S. President Donald Trump's hush money trial. The day ended with Madeleine Westerhout, a former Trump executive assistant, on the stand who will be back when the trial commences. (Photo by Michael M. Santiago/Getty Images) MORE LESS
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NEW YORK — There are a few kinds of witnesses we’ve met in the Trump trial.

There are the strictly custodial witnesses: workers for AT&T, Verizon, legal services firms, book publishers — these are people who were plucked from their corporate day jobs to testify to records that their employer has provided. It’s clearly a strange experience for these people, but they’re here to testify on behalf of the legal entity that they represent.

Then there are the Trump Organization employees. These have encompassed accountants, bookkeepers, a controller — they are the professionals who managed the financial plumbing of the Trump Organization. They provided critical if not somewhat staid testimony about the logistical infrastructure of the alleged illegal coverup of the reimbursement scheme — how Cohen received the reimbursements, how they were marked, and how invoices and checks flowed from Manhattan to the White House for Trump to sign.

But the witness who testified on Thursday afternoon and Friday morning fits into a different category. Madeleine Westerhout was an executive assistant. She was one of a few secretaries, often young women, charged with managing Trump’s personal schedule and affairs.

Their tasks were more ambiguous than those of the other witnesses. Westerhout sat outside the Oval Office along with Hope Hicks. Their duties included controlling access to Trump, handling his correspondence, working with his longtime executive assistant Rhona Graff to manage his schedule and rolodex, and communications strategy. Both Hicks and Westerhout entered Trump’s orbit in their early-to-mid-20s.

It’s a portfolio that demanded loyalty to, above all, Trump himself, a fact that became clear in particular during Westerhout’s testimony.

Throughout her time on the stand, Westerhout went out of her way to profess loyalty to the man she was testifying against. She made a show of explaining how the Stormy Daniels allegations must have caused Trump to worry about his family, while holding back from any speculation that may have reflected poorly on the president.

Prosecutors asked her, for example, about a $650 picture frame that had been submitted as a possible personal expense during his presidency. It was to carry a picture of Trump’s mother, Westerhout testified.

For the DA, the value was clear: this was a relatively minor expense — far less money than the $420,000, separated in monthly checks of $35,000, that Cohen received in “legal expenses” from two Trump bank accounts. And yet Westerhout was involved in correspondence about whether Trump himself would want to weigh in on the expense. Prosecutors showed an exhibit showing emails discussing whether Trump wanted to buy the frame, minus a 15 percent discount.

“Please note that the frames are on the pricey side…about $650 minus %15 discount. Does DJT want to spend that much?” Graff wrote to Westerhout in a June 2017 email.

Westerhout testified that she approved the expense at her discretion, before addressing Trump from the stand: “Sorry, sir.”

It was a critical moment for prosecutors, who then followed up: Was it typical for Trump to weigh in on minor expenses?

“I don’t recall any other instances,” she said. “This one was important and special because this was for a photo of his mother.”

The response stopped prosecutors from taking the point to its logical conclusion: that if Trump was personally approving $650 picture frames, a monthly payment of $35,000 could not have escaped his notice. Prosecutors moved on, asking Westerhout about the circumstances of her firing.

WASHINGTON, DC – FEBRUARY 2: Madeleine Westerhout watches as President Donald Trump speaks during a meeting with North Korean defectors in the Oval Office at the White House in Washington, DC on Friday, Feb. 02, 2018. President Donald Trump talked to reporters and members of the media about the release of a secret memo on the F.B.I.’s role in the Russia inquiry. (Photo by Jabin Botsford/The Washington Post via Getty Images)

“I said some things at a dinner that should not have been said,” Westerhout testified. “That mistake cost me my job.”

The things that “should not have been said,” per a Politico report from 2019, included a remark that Trump did not want to be photographed with his daughter Tiffany due to her weight, and that Westerhout was closer to Trump himself than many of his children.

Westerhout began to break down in tears during this portion of her testimony. She repeated that she felt terribly about the episode, and had tried to learn from it and move on. Prosecutors showed jurors an exhibit of the cover of Westerhout’s book, which features Westerhout helping Trump review papers at what appears to be the Resolute Desk.

Her appearance at the trial felt, at times, as if she saw an opportunity to demonstrate to Trump that, in spite of her firing, she remains loyal to the presumptive GOP nominee. She continued to sob as she recounted the last time she saw Trump. It was at a fundraiser last year in Orange County. Westerhout recalled, through tears, how she called an unnamed Trump aide before attending to ask if she could stop by the event so she could see him.

The whole thing was a strange and very performative display of loyalty. One fellow reporter remarked to me after that Westerhout reminded her of one of the Stepford Wives — obsequious and almost robotic.

The whole performance may have taken place, at this point in the trial, by design. Prosecutors had Westerhout testify immediately after a witness from the publishing house Harper Collins narrated excerpts of a book in which Trump talks about how he divides those around him into a binary: the loyal and the disloyal.

She read out excerpts, including one in which Trump describes how he puts “the people who are loyal” to him “on a high pedestal and take care of them very well. I go out of my way for the people who were loyal to me.”

For the disloyal, “My motto is: Always get even. When someone screws you, screw them back in spades.”

Westerhout gave her performance of loyalty to Trump immediately after jurors heard those excerpts. It contextualized Westerhout’s testimony both in the moments where she did not help prosecutors — as in the questioning around the $650 frame — and when she hurt the defense.

Westerhout had testified on cross-examination to defense attorney Susan Necheles that she believed Trump was concerned about the Stormy Daniels story because the story “would be hurtful to his family.”

It was an opportunity for the defense, which has tried to argue that Trump was motivated to pay the hush money not out of fear of losing the election, but out of fear of damaging his family ties. It’s one thing to pay off a porn star out of political expediency — that may not be very sympathetic to jurors. But buying the silence of a porn star to protect your family — now there’s an argument for leniency.

Necheles pushed on that, asking Westerhout if Trump had told her specifically that it had been hurtful to his family.

Westerhout said no, he had not.

“I could just tell that the whole situation was very unpleasant,” she recalled.

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