Leaked Texts Shed Light on Kimberly Guilfoyle and Donald Trump Jr.’s Split

Newly obtained text messages offer a fresh look at the turbulent collapse of Donald Trump Jr. and Kimberly Guilfoyle’s engagement.

Kentucky attorney and Republican donor Eric Deters, whose exchanges with Guilfoyle were previously reported by The Wall Street Journal, says he witnessed the relationship’s deterioration after hosting the pair at his events for several years.

Deters founded the annual Patriot’s Day Freedom Fest to oppose COVID-19 medical mandates, launching the event in 2020 with a lineup that attracted prominent MAGA figures.

In the weeks before the gathering, everything appeared to be going smoothly.

On August 6, 2024, Guilfoyle texted Deters to wish him a happy birthday on behalf of herself and Don Jr.

“Hey Eric happy birthday from me and Don Jr. Hope you have a great day!!!” she wrote.

But when the festival took place several weeks later, on September 14, 2024, Deters says the relationship between Guilfoyle and Don Jr. had grown noticeably cold.

According to Deters, Don Jr. avoided sitting beside or speaking with Guilfoyle during rides to and from the airport and inside the VIP tent. Staff members and guests, he said, could not miss the uncomfortable tension.

Deters told Our News Outlet that Guilfoyle, worried Don Jr. would be upset if he saw her drinking, asked Deters’ wife and a friend to discreetly bring her alcohol during the festival. He compared the alleged effort to a teenager hiding drinks from her parents.

Guilfoyle’s fondness for Champagne and social gatherings has been widely reported. After she was selected to serve as President Donald Trump’s ambassador to Greece, insiders reportedly encouraged her to behave cautiously, warning that a posting among the Aegean islands and perpetual summer parties did not amount to an invitation to celebrate without limits.

When the event ended, Deters said Guilfoyle asked to take home all of the remaining catered food from the VIP area—a request he considered unusual.

He also said Guilfoyle asked him to praise her in front of Don Jr., apparently hoping to “win back his favor.”

The day after the festival, Our News Outlet published an exclusive report featuring photographs of Don Jr. displaying affection toward Bettina Anderson, who is now his wife, during a private brunch.

The images were taken on August 17, 2024, and witnesses said the pair kissed several times.

Two days after the report appeared, Deters texted Guilfoyle to express concern about the relationship problems described in the story. Guilfoyle responded angrily, repeatedly insisting that there were no troubles in “Jr. World.”

But text messages show the discord behind the scenes. 

‘You doing ok?’ Deters texted on September 17, 2024. ‘Saw Our News Outlet report. I have that app. I could tell Saturday that you were hurting.’

Deters was referring to the day they had spent together at the Freedom Fest.  

Guilfoyle snapped back, calling the story ‘fake news,’ and insisting, ‘I wasn’t hurting wtf.’

In another undated exchange, Guilfoyle complained about Don Jr’s now wife, while appearing to dismiss the same reporting. 

‘I was having a f***ing great time Saturday and we had a f***ing amazing time when we got home Saturday night that’s nonsense. That’s his ex-wife’s friend,’ Guilfoyle writes in the text to Deters.

‘It’s all lies, but she’s a cloud chasing horror that plays the story in Our News Outlet to get attention,’ she says in the text, falsely claiming that Bettina sent her own bikini photographs to be included. 

The reference to ‘his ex-wife’s friend’ likely means Vanessa Trump, who shares five children with her ex-husband Don Jr.

Vanessa and Bettina were friends when Bettina started dating Don Jr, later marrying him in May 2026.

‘What a c***,’ Deters responded to Guilfoyle’s messages about Bettina at the time. ‘To increase her exposure.’

A source close to Bettina and Don Jr called Guilfoyle ‘clearly delusional.’

‘There is zero truth to her claim that Bettina had anything to do with that story,’ the source said.

Guilfoyle and Don Jr first started dating midway through his father’s initial presidential term. After getting engaged in 2020, the couple called it quits four years later, after Don Jr was spotted growing close to Bettina.

Months later, Trump nominated Guilfoyle as Ambassador to Greece in December 2024.

Following her Senate confirmation last September, Guilfoyle’s tenure as ambassador has been mired in controversy.

Our News Outlet reported earlier this week that the State Department is officially investigating complaints into her allegedly ‘tyrannical’ leadership and lavish corporate perks and Champagne-filled lifestyle.

The Trump administration is facing mounting pressure following the revelation of the probe, in addition to Wall Street Journal reporting on leaked texts between Guilfoyle and Deters detailing a $100,000 payoff request for an Amex bill. 

Trump’s top deputies, Vice President JD Vance and Secretary of State Marco Rubio, have been pressed about her conduct this week. 

A touchy Rubio snapped at reporters asking about Guilfoyle’s controversies while on official travel to Greece this week, saying ‘I don’t even know what’s true or not true.’

‘You guys somehow walk around thinking that because some source told you something and you reported it, it’s the gospel. It’s not the gospel. It’s not the gospel for me.’

Vance similarly brushed aside questions, calling them ‘hypothetical,’ but admitted that he ‘doesn’t love’ what’s being reported on her spending and expenses.

‘Well, so… with that hypothetical, obviously I don’t love that, but I, you know, I don’t know exactly who you’re talking about,’ he said. ‘I don’t know the full details.’ 

Deters went on to tell Our News Outlet that during the festival, Don Jr was seemingly focused entirely on his political strategy.

He claimed that Don Jr privately boasted to him that he used all of his ‘political capital’ to secure JD Vance on the presidential ticket in 2024, adding that the move set him up well for 2028 with Vance at the top of the ticket.

Trump tapped Vance, a young Senate rookie, during the Republican National Convention in July 2024, days after he survived an assassination attempt at a campaign rally. 

The travel arrangements for the 2024 event were equally fraught, as the couple arrived on separate flights at different airports, according to Deters. Don Jr landed at private airport Lunken, while Guilfoyle arrived at Cincinnati’s main airport, about 30 minutes away.

After picking up Guilfoyle, Deters says he was forced to drive at extreme speeds to meet Don Jr before he disembarked, earning himself the nickname ‘Jason Statham’ from Guilfoyle.

The high-speed drive turned chaotic when Deters accidentally missed an exit and drove his SUV down a steep grass embankment. 

As Guilfoyle and her assistant, Cassidy, bounced around the cabin, Guilfoyle shrieked: ‘I might lose my breast implants!’ according to Deters.

Behind closed doors, Guilfoyle’s frustration with the event and the Trump family erupted when she reportedly candidly branded all Trump men as ‘narcissistic a**holes,’ according to Deters.

The State Department and Guilfoyle’s lawyer did not return Our News Outlet’s requests for comment. 

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