In a surprising turn of events, former U.S. President Donald Trump has distanced himself from Kimberly Guilfoyle, despite her previous engagement to his eldest son, Donald Trump Jr. The comments were made during a White House briefing on 13 October, shortly after news broke that Guilfoyle had been asked to resign from her role as U.S. ambassador to Greece due to concerns regarding her conduct.
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Trump’s remarks came in response to a question from ABC News correspondent Rachel Scott, who pointed out that Guilfoyle, now 57, was “almost a member of your family.” Trump quickly contradicted this statement, stating, “No, she wasn’t a member of my family. She, I guess, dated my son a long time ago.” The president then praised Guilfoyle for her work in Greece, noting that she had been “doing a good job” but that he and his team were uncomfortable with reports about her conduct.
This latest comment represents a striking shift in Trump’s attitude towards Guilfoyle, especially considering his glowing remarks made only six months prior. During a celebration of Greek Independence Day at the White House in March, Trump referred to Guilfoyle as a “friend” and “an inspiration to a lot of people.” He affectionately called her “Kimberlay,” a name he mentioned while expressing optimism for her future tenure as ambassador.
Guilfoyle was officially nominated for the ambassadorship in December 2024, a decision announced by Trump on his social media platform, Truth Social. In his post, he described Guilfoyle as a “close friend and ally” with a strong background in law, media, and politics, and asserted that her qualifications made her well-suited to strengthen U.S.-Greece relations on various fronts, including defence cooperation and economic innovation.
However, reports from the Wall Street Journal alleging that Guilfoyle solicited financial assistance from a Trump donor shortly before her Senate confirmation hearing led to her abrupt ousting from the ambassadorship. Specifically, it was claimed she requested that the donor cover $100,000 worth of credit card expenses. In the wake of these allegations, Giulfoyle took to social media to confirm her resignation, asserting, “These allegations are false, and I intend to vigorously defend my name, my reputation, and my integrity.”
Guilfoyle’s career has spanned various avenues, including a prior role as a legal analyst for Fox News. She began dating Donald Trump Jr. in 2018, following years of acquaintance. Their romance quickly blossomed, leading to an engagement on New Year’s Eve in 2020. However, the couple dissolved their relationship in 2024 without much public fanfare.
Since their split, Donald Trump Jr. has moved on, recently announcing his engagement to socialite Bettina Anderson at the White House. The couple wed in May 2025, almost a year after his relationship with Guilfoyle ended. Guilfoyle, reflecting on her past with Donald Jr., stated that she wished him “all the best,” demonstrating a sense of goodwill following their separation.
Guilfoyle’s personal history includes a previous marriage to California Governor Gavin Newsom from 2001 to 2005, as well as a later marriage to designer Eric Villency, with whom she shares a son, Ronan. The dynamics of these relationships have frequently made headlines, and her subsequent involvement with Trump Jr. placed her further into the spotlight within the politically charged environment surrounding the Trump family.
As the situation continues to develop, Guilfoyle stands firm in her commitment to her professional reputation and integrity in light of the scrutiny she faces following her resignation. This incident highlights not only the complexities of personal relationships within political spheres but also the intense media attention that figures associated with the Trump family attract.
In the wake of these recent events, both Trump and Guilfoyle find themselves navigating the implications of their past connections while dealing with the present circumstances that have significantly altered their public narratives.