Kimberly Guilfoyle’s Reported Return to Donald Trump Jr. Draws Attention

Kimberly Guilfoyle became accustomed to an unusually lavish lifestyle during her short, high-profile tenure as the US ambassador to Greece. Her next home, however, may offer far fewer of those diplomatic comforts.

The former MAGA loyalist remains at Jefferson House, the grand ambassadorial residence in Athens’ affluent Kolonaki district. The property drew attention in March after she reportedly used taxpayer funds to install a $58,000 basketball court in its landscaped grounds.

Now that her diplomatic appointment has ended suddenly, Guilfoyle must leave the residence to make way for the incoming ambassador.

Finding a new base could be complicated. The mother-of-one no longer has her former home in Jupiter, Florida, after ex-fiancé Donald Trump Jr bought out her share in August.

Her departure follows months of scrutiny over her spending and social life in Greece, including appearances at Paris Fashion Week and luxury getaways to the celebrity-favorite island of Mykonos.

The controversy intensified after reports from the Daily Mail and the Wall Street Journal said Guilfoyle had sought $100,000 from a Trump donor to settle an American Express bill. The reports also alleged that she approached wealthy Greek businessmen for money to purchase a G-Wagon.

Guilfoyle is expected to head back to the United States, although her next destination remains uncertain. It is not clear whether she currently owns property after Trump Jr paid $7.5 million for her interest in their Jupiter mansion over the summer.

Her previous US properties included a Hamptons home purchased with Trump Jr and sold in March 2021, as well as an upscale New York apartment she put on the market for $5 million in 2020.

“She will probably move back to Florida because it is where her son may want to return,” a source told the Daily Mail. “She won’t want to be too far away from him.”

Ronan, her 20-year-old son with her first husband, Eric Villency, was reportedly living with Guilfoyle in Athens.

Oxbridge Academy, the West Palm Beach prep school Ronan attended, announced on Instagram in May 2025 that he had been accepted to the University of Miami. The Daily Mail also reports that he spent some time at the American College of Greece’s Deree School.

Villency, 51, and Guilfoyle have remained on friendly terms since their 2009 separation, and the interior design executive owns a home in Palm Beach. However, people familiar with the situation say Guilfoyle moving in with her former husband is considered very unlikely.

The property settlement with Trump Jr may have left Guilfoyle with substantial funds, but maintaining her preferred lifestyle while buying a home in Palm Beach could still prove costly. The average property in the area sells for about $2.2 million, according to the report.

Returning to Palm Beach would also put Guilfoyle in close proximity to Trump Jr and Anderson, making an unavoidable reunion with her former fiancé increasingly likely.

Text messages obtained by the Daily Mail last week offered a glimpse into the painful breakup. The messages reportedly showed that Guilfoyle, 57, was stunned by photographs of Trump Jr holding hands with Anderson and attempted to hold Anderson, 39, responsible for their release.

The Daily Mail published the images in September 2024, while Guilfoyle and Trump Jr were still officially engaged.

In texts exchanged with GOP donor Eric Deters, Guilfoyle tried to dismiss the story as ‘fake news’ and lashed out at Anderson calling her ‘a cloud chasing horror’ before falsely accusing her of submitting her own bikini pictures to the Daily Mail.

She went on: ‘It’s all lies, but she’s a cloud chasing horror that plays the story in the Daily Mail to get attention.’

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Palm Beach is also the location of President Trump’s ‘winter White House’ Mar-a-Lago, while Don Jr’s sister Ivanka and her husband, Jared Kushner, also live nearby. 

Guilfoyle had been a fixture in the Trump family inner circle throughout her six-year relationship with and engagement to Don Jr – invited to private gatherings and becoming privy to their personal conversations.

The couple broke off their engagement in late 2024 as Don Jr and Bettina Anderson’s relationship blossomed, but Guilfoyle maintained ties to the family after securing her appointment as US ambassador to Greece by President Trump months later. 

Part of the reason Guilfoyle was handed the plum ambassadorship was allegedly to get her away from Palm Beach where, insiders feared, she might wreak havoc after being cut out of the inner circle.

Instead, she was handed the consolation prize of a glamorous posting to the Greek capital – well out of the way as Don Jr went official with Anderson and married her in a lavish Caribbean wedding in May of this year.

‘Kimberly knows everything. She was way inside that family and political operation for years,’ one insider told the Daily Mail.

Another source said: ‘Keeping Kimberly happy keeps Kimberly quiet.’

A third source added: ‘Kimberly wasn’t sent to Greece just because of her skills. It also solved a complicated personal problem.

‘Having her thousands of miles away worked for everyone.’

Allies of the president are said to be relieved that Guilfoyle is leaving her post, but insiders have warned the Trump family may not have heard the last of her.

‘Having her back in America would be a nightmare. Kimberly knows where the bodies are buried,’ one source told the Daily Mail. 

‘She knows the people, the secrets, the fights, the relationships.

‘Nobody wants an angry Kimberly back home with nothing to lose.’ 

At the site of the embassy late Tuesday after her resignation, the entrance showed almost no signs of life, with just three working lights perched switched on.

Two security guards were left manning the main entrance. At around 7.07pm local time a BMW, escorted by a second car, drove into the compound.

One of the US embassy’s longest serving staff members told the Daily Mail that Guilfoyle’s rapid decline was ‘unprecedented.’

‘We have never seen such a violent beheading of the mission. Usually, these push outs or terminations happen quietly. This was abrupt. But was it really an ending?

‘She had a cocky and brass air to her. And as time passed, it became more and more unbridled,’ continued the staffer.

Guilfoyle’s ultimate humiliation came as Trump’s new press secretary Katie Zacharia revealed the ambassador had been asked to resign one day after the president said he was ‘not happy’ with negative reports about her high-rolling lifestyle. 

The Daily Mail has reached out to Kimberly Guilfoyle for comment.