The truth about Kimberly Guilfoyle and Donald Trump’s relationship is far from the mutual admiration one might expect. While Guilfoyle often gushes over Trump at every opportunity, the former president doesn’t seem to return the sentiment. On Trump’s birthday in June 2024, Guilfoyle took to Instagram to praise him, writing, “Your unwavering patriotism, strength, and leadership continue to inspire millions of Americans,” alongside a photo of the two together.
However, her social media praise paled in comparison to the fervor she displayed at the Republican National Convention. “This election will decide the fate of our great nation, and that is why we must elect President Donald John Trump,” Guilfoyle passionately declared, attempting to rally the crowd. Yet, Trump himself seemed unmoved by her words. Cameras captured him during her speech, barely applauding and with his eyes cast downward, not even looking at the podium. Viewers took note, with one person commenting on X, formerly Twitter, “You MUST praise Donald Trump, even if he can’t stand the sight of you.” The moment appeared to confirm that Trump is less than enthusiastic about Guilfoyle, perhaps growing weary of her presence and her choice of outfits on the campaign trail.
Even Guilfoyle’s fiancé, Donald Trump Jr., appeared disinterested during her RNC speech. “His body language is something else. It screams, ‘How did I get stuck with this nut job?'” another user on X observed. Reports have circulated that Trump Sr. showed signs of disapproval early on in his son’s relationship with Guilfoyle.
Guilfoyle’s professional relationship with Donald Trump has also been rocky. In October 2019, when Trump was still in office, it was reported that the former Fox News anchor lobbied to become his White House press secretary but was rejected. An aide at the time commented, “Even he can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads” told The Atlantic. Guilfoyle’s interactions with Trump have reportedly been complicated since then. When Donald Trump Jr. first brought her as a guest to a White House event, Trump allegedly insisted that all future guests be pre-approved.
By January 2020, Trump was willing to give Guilfoyle a chance, appointing her as the head of the Trump Victory re-election campaign. However, she struggled in the role, and by July 2020, reports from Politico suggested she had failed to thrive.
In 2021, Guilfoyle transitioned to working on Governor Eric Greitens’ campaign, a move that reportedly irritated Trump. “Trump thinks Greitens is problematic, and that Kim is annoying,” an insider told Politico. It wasn’t just Trump Sr. who had grown tired of Guilfoyle. In November 2022, Ivanka Trump cropped Guilfoyle out of a group photo at Tiffany Trump’s wedding, sparking rumors that Ivanka was signaling her dislike. Ivanka eventually posted the full photo to her Instagram Stories but left the cropped version on her main page. “The vibe is that the family doesn’t like Kim. She is trying too hard to be in the family,” a source told Page Six in December 2022.
By July 2024, speculation arose that Donald Trump Jr. himself was growing weary of Guilfoyle, fueled by her shift on Instagram from sharing pictures with him to focusing on memes and political commentary. This change, combined with Trump Jr.’s lackluster response to her RNC speech, only intensified rumors that the relationship might be on the rocks.