Donald Trump’s apparent distaste for Kimberly Guilfoyle, fiancée of his son Donald Trump Jr., has fueled ongoing speculation about tensions within the Trump family. While Guilfoyle is a prominent conservative fundraiser and media personality, her relationship with the Trump clan appears complicated, reportedly hindered by Trump Sr.’s strong preference for his daughter, Ivanka Trump.
Rumored Rivalry
Reports suggest that Donald Trump’s disapproval of Guilfoyle dates back to 2019 when she allegedly drew attention away from Ivanka and Jared Kushner during a Fourth of July event. Sources claim this incident prompted Trump to limit Guilfoyle’s presence at family gatherings, including discouraging her attendance at Thanksgiving, as reported by Irish Star.
Though the White House dismissed these reports as false, speculation persisted. In 2021, insiders alleged that Trump found Guilfoyle “annoying,” a sentiment never publicly expressed about Ivanka. Journalist Marc Fisher has noted that Trump’s dynamic with Ivanka is starkly different from his relationships with his other children, describing a “softness” and “gentleness” in his demeanor toward her. Fisher explained, “When he is talking about Ivanka versus any of his other children, it’s just night and day.”
Ivanka’s Unique Position
Ivanka has long occupied a special place in Donald Trump’s personal and professional life. Her father’s frequent praise of her, often veering into controversial territory, underscores this dynamic. Trump famously said during a 2006 appearance on The View, “I’ve said if Ivanka weren’t my daughter, perhaps I’d be dating her.”
In 2015, he remarked, “Yeah, she’s really something, and what a beauty, that one. If I weren’t happily married and, ya know, her father…” These comments highlight Trump’s distinct favoritism toward Ivanka, which may explain his resistance to Guilfoyle’s influence.
Guilfoyle’s Outsider Status
Since her relationship with Donald Trump Jr. began in 2018, Guilfoyle has often been portrayed as an outsider within the Trump family. Reports from The Daily Beast describe her exclusion from family pictures during a Palm Beach celebration and moments of visible distance between her and Donald Jr. Recent rumors have further complicated matters. In September, reports surfaced of Donald Trump Jr. spending time with Palm Beach socialite Bettina Anderson, with sources claiming, “They’re not trying to hide it. They’ve been seen together all over Palm Beach.”
Neither Trump Jr. nor Guilfoyle has commented on these claims, but their public appearances have reportedly been marked by tension. This complex dynamic within the Trump family reflects deeper divides, with Guilfoyle struggling to gain full acceptance amidst Donald Trump’s unwavering favoritism for Ivanka.