Who is Madeleine Westerhout and what was her role in the Trump White House?
Executive summary
Madeleine Westerhout is an American political aide who served as Personal Secretary to President Donald Trump from 2017 until early 2019 and was promoted to Director of Oval Office Operations from February to August 2019, a role that made her a primary gatekeeper for the president’s schedule and calls [1] [2]. Her tenure ended after she was fired for recounting private details about the Trump family to reporters at an off‑the‑record dinner, and she later wrote a memoir and continued a career in pro‑Trump circles [1] [3] [4].
1. Background and rise into the West Wing
A College of Charleston political science graduate who began her career at the Republican National Committee, Westerhout joined Trump’s transition team and was named Special Assistant and Executive Assistant to the President at the start of the administration, quickly becoming the on‑the‑ground aide who managed the president’s calls, schedule flow and access to the Oval Office [2] [5] [6]. Public salary disclosures from 2018 listed her compensation for the role, underscoring the official and senior nature of her duties inside the West Wing [1].
2. Director of Oval Office Operations — what the job meant in practice
As Director of Oval Office Operations, a post she held officially from February to August 2019, Westerhout worked immediately outside the Oval Office and functioned as the liaison between the president and West Wing staff, Cabinet offices, and outside stakeholders — effectively controlling who reached the president and what he saw during a packed schedule [1] [5] [7]. Contemporary reporting and later interviews describe the job as “gatekeeper” work: screening calls, coordinating the president’s flow, and sometimes physically presenting documents and checks for signature [5] [7] [6].
3. The firing and the controversy over leaks and private remarks
Westerhout was dismissed in August 2019 after reporters published comments she made at an off‑the‑record dinner in which she discussed the Trump family and suggested she had closer ties to the president than his daughters, remarks that the White House said breached trust and confidentiality [1] [8] [9]. Accounts vary about context and intent — Westerhout later said the comments were made after drinks and were a mistake, while some former colleagues interpreted the episode as confirmation of longstanding concerns about loyalty and information control inside the administration [3] [4] [8].
4. Post‑White House activity, testimony, and memoir
After leaving the White House, Westerhout published a memoir, Off the Record, recounting her time in the administration and defending aspects of her relationship with Trump, and she later worked in roles tied to pro‑Trump or Republican networks, including at American Global Strategies [3] [5]. In May 2024 she testified under subpoena in the Manhattan “hush money” trial, describing the procedural reality of payments and paperwork presented to the president for signature — testimony that placed her as a witness to administrative practices inside the residence and Oval Office [1] [7] [6].
5. Public perception, competing narratives and possible agendas
Public portrayals of Westerhout range from loyal confidante and sympathetic former aide to a staffer whose loose talk exposed insider dysfunction; conservative outlets and her own memoir emphasize her affection for Trump and cast her firing as a regrettable lapse, while other reporting stresses that senior officials long suspected her of disloyalty and that the episode illustrated broader problems with information discipline in the West Wing [3] [4] [8]. Sources that worked with or for Trump have incentives to rehabilitate or defend former aides — for example, corporate bios and publisher blurbs frame her as a trusted “gatekeeper” and continue to benefit from her association with the administration [5] [3].
6. What can and cannot be concluded from available reporting
Available reporting and her own public statements make clear what her official titles and core duties were, that she was fired after discussing private family matters with reporters, that she later published a memoir and testified in the Trump trial, and that opinions about her loyalty differ by source [1] [9] [3] [7]. Reporting does not settle every contested claim about private interactions or unsourced allegations that have circulated in other accounts, and where the record is silent the sources provided do not support definitive conclusions beyond what she and contemporaneous news reports state [10] [11].