The engagement of Donald Trump Jr to socialite Bettina Anderson has reportedly drawn a bitter and sceptical response from his former fiancée, Kimberly Guilfoyle. Sources close to Guilfoyle suggest she questions the authenticity of the relationship and believes the Trumps orchestrated her prestigious diplomatic posting to get her out of the country.
Ex-Fiancée's Doubts and Delayed Separation
According to insiders speaking to People magazine, Kimberly Guilfoyle, 56, does not believe her ex-fiancé's new relationship is the "real deal." She is said to think that Anderson, 39, is not well-suited for Trump Jr and is more attracted to the prestige of the Trump family name than to the man himself. "She feels Bettina is more interested in the prestige and attention that comes with being connected to the Trump family," a source revealed.
The separation between Guilfoyle and Trump Jr, which ended their six-year relationship in 2024, appears to have been a protracted process. An insider disclosed that Guilfoyle only recently removed her belongings from the 47-year-old Trump heir's home, and he likewise had possessions, including clothes and shoes, at her residence until not long ago. This overlap occurred despite Trump Jr reportedly introducing Bettina Anderson as his girlfriend months before his split from Guilfoyle was finalised.
A Model Fiancée and a Strategic Posting
Donald Trump Jr's engagement to Bettina Anderson was announced publicly by his father, former President Donald Trump, during a White House Christmas Party. Anderson, a model and daughter of a former bank president, is seen by some as a figure who would impress the Trump patriarch. "Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach, is something that would impress him," a source commented.
Following the 2024 election victory, Guilfoyle was nominated by President Trump to serve as the U.S. Ambassador to Greece, a role confirmed by the Senate a year later. However, this appointment is now shrouded in claims of ulterior motives. Insiders allege the posting was a strategic move by the Trump family. "They are trying to send Kim abroad," a source told People. "They waited for the election to pass, but they didn't want the split to get in the way of anything to hurt Donald in the election."
Awkward History and Personal Jibes
The dynamics are further complicated by Guilfoyle's marital history. She was married to California Governor Gavin Newsom, a prominent political opponent of Donald Trump, from 2001 to 2006. This connection became a source of awkward humour, as reported in the book 'The Hill to Die On' by Anna Palmer and Jake Sherman. At a 2024 fundraiser, Trump reportedly singled out Guilfoyle while criticising Newsom's policies, quipping, "Kimberley, you know him, right?" The joke was met with tepid laughter.
Contrasts have also been drawn between Guilfoyle and the new fiancée. Sources claimed last year that Trump Jr criticised Guilfoyle's professional fashion sense, telling people she was "uptight" and that her signature tight dresses and high heels "need to go." This stands in stark contrast to his public gushing over Anderson at the engagement announcement.
The Independent has contacted representatives for both Donald Trump Jr and Kimberly Guilfoyle for comment on these reports.
