Leaked text messages reveal Kimberly Guilfoyle’s explosive reaction to Don Jr and Bettina Anderson’s cozy date pics… and her sneaky ‘high schooler’ moves to hide party lifestyle that’s put her in Trump admin’s crosshairs

By ELINA SHIRAZI, US SENIOR POLITICAL REPORTER

Published: 11:33 EDT, 10 October 2026 | Updated: 11:42 EDT, 10 October 2026

Explosive new details about the messy, behind-the-scenes breakdown of Donald Trump Jr and Kimberly Guilfoyle’s broken betrothal are revealed in text messages obtained by the Daily Mail.

Kentucky attorney and GOP donor Eric Deters, whose messages with Guilfoyle were reported in the Wall Street Journal, says he had a front-row seat to the unraveling of the MAGA power couple after hosting them at his events over several years.

Deters launched the annual Patriot’s Day Freedom Fest to protest COVID-19 medical mandates, an event filled with MAGA royalty, beginning in 2020.

All seemed well in the weeks leading to the event.

On August 6, 2024, Guilfoyle sent Deters a text message, wishing him a happy birthday on behalf of her and Don Jr.

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

But by the time the annual festival arrived just weeks later on September 14, 2024, the dynamic between Guilfoyle and Don Jr had turned entirely arctic, he says.

According to Deters, during the festival, Don Jr refused to sit near or speak to Guilfoyle during car rides to and from the airport, as well as inside their VIP tent, leaving staff and guests taking note of the awkward dynamic.

Eric Deters is pictured above alongside Kimberly Guilfoyle and Pam Bondi (Source: Eric Deters)

On August 6, 2024, Guilfoyle sent Deters a text message, wishing him a happy birthday (Source: Eric Deters)

Kentucky attorney and GOP donor Deters says he had a front-row seat to the unraveling of the MAGA power couple after hosting them at his events over several years (Source: Eric Deters)

Fearing Don Jr’s disappointment if he caught her drinking, Deters says Guilfoyle recruited Deters’ wife and her friend to secretly sneak alcohol to her during the festival, acting ‘like a high schooler’ hiding booze from her parents, Deters claimed to the Daily Mail.

Guilfoyle’s affinity for Champagne and parties have widely been documented, and insiders urged her to be on good behavior after she was tapped to be President Donald Trump’s Greek Ambassador, cautioning that an assignment amid Aegean islands and endless summers wasn’t a green light for nonstop partying.

At the conclusion of the event, Guilfoyle insisted on packing up and taking all the remaining catered VIP food home with her, an odd request in Deters’ eyes.

Deters said she also begged him to compliment her in front of Don Jr in the hopes of ‘winning back his favor,’ Deters detailed.

The day after the festival ended, the Daily Mail published an exclusive report revealing photos of Don Jr canoodling with his now wife Bettina, during an intimate brunch date.

The exclusive photos were taken on August 17, 2024, and witnesses say they kissed several times.

A photo obtained exclusively by the Daily Mail showed Don Jr having brunch with Palm Beach socialite Bettina Anderson in mid August 2024 – with then-fiancée Kimberly Guilfoyle nowhere in sight

Months later in December 2024, Don Jr and Bettina were spotted leaving dinner in Palm Beach

Two days after the story was published, Deters reached out via text to express concern over her relationship troubles outlined in the Daily Mail report. Guilfoyle snapped, repeatedly denying there were any issues 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.

Guilfoyle snapped back, calling the story ‘fake news,’ and insisting, ‘I wasn’t hurting wtf’ (Source: Eric Deters)

The reference to ‘his ex-wife’s friend’ likely means Vanessa Trump, who shares five children with her ex-husband Don Jr (Source: Eric Deters)

Deters has shared a trove of revealing messages about Guilfoyle and Trump Jr’s split (Source: Eric Deters)

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.

The president’s son, who began dating Guilfoyle shortly after his split from first wife Vanessa Trump in 2018, was spotted locking lips with the model during the outing, according to witnesses (Source: Kimberly Guilfoyle/Instagram)

Donald Trump Jr and Bettina at the couple’s lavish bridal shower at Mar-a-Lago in April (Source: yazchernandez/Instagram)

Bettina and Don Jr had a lavish May wedding party and posted never-before-seen photos on Instagram on Monday (Source: Bettina Trump/Instagram)

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.

Don Jr is pictured with now-wife Bettina Anderson in September along with his kids Chloe and Spencer

Bettina joined Don Jr on the president’s travel to Ireland over the summer

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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