Leaked Texts Reveal New Details on Kimberly Guilfoyle and Don Jr.’s Split

New text messages obtained by the Daily Mail offer a closer look at the reported turmoil behind Donald Trump Jr. and Kimberly Guilfoyle’s ended engagement.

Eric Deters, a Kentucky attorney and Republican donor 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 in 2020 as a protest against COVID-19 medical mandates. The gathering quickly became a showcase for prominent MAGA figures.

In the weeks before the festival, however, there appeared to be no obvious sign of trouble.  

On August 6, 2024, Guilfoyle texted Deters to wish him a happy birthday, signing the message from herself and Don Jr. 

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

By the time the festival took place on September 14, 2024, Deters says the atmosphere between Guilfoyle and Don Jr. had become noticeably cold.

Deters claims Don Jr. avoided sitting beside Guilfoyle or speaking with her during the airport transfers and inside the VIP tent. The strained interaction was reportedly noticed by people working at and attending the event. 

Deters also told the Daily Mail that Guilfoyle, concerned Don Jr. might 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 hiding drinks from parents as a teenager. 

Guilfoyle’s taste for Champagne and social events has been widely reported. After she was selected as President Donald Trump’s ambassador to Greece, people close to her reportedly advised her to exercise restraint, emphasizing that a posting among the Aegean islands and a warm climate did not amount to an invitation to party constantly.

Deters said that after the festival, Guilfoyle asked to take all of the remaining catered food from the VIP area home—a request he regarded as unusual.

He also said she asked him to praise her in front of Don Jr., allegedly hoping to improve the strained relationship and regain his approval. 

The day after the festival, the Daily Mail published an exclusive report featuring photographs of Don Jr. in an affectionate moment with 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 check on her following the relationship revelations described by the Daily Mail. She responded angrily and repeatedly insisted that there were no problems in “Jr. World.”

But text messages show the discord behind the scenes. 

‘You doing ok?’ Deters texted on September 17, 2024. ‘Saw the Daily Mail 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 the Daily Mail 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.

The Daily Mail 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 the Daily Mail 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 the Daily Mail’s requests for comment. 

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