Trump Women Reveal Brutal Feelings About Kimberly Guilfoyle

Kimberly Guilfoyle is reportedly struggling after President Donald Trump publicly distanced himself from her, saying she was never part of the family. The former ambassador’s difficult moment has been compounded by the silence of women she once viewed as close relatives, Our News Outlet has learned.

Guilfoyle, 57, resigned as Trump’s ambassador to Greece earlier this week after a series of damaging headlines focused on her lifestyle and spending.

People within Trump’s inner circle have not universally rallied behind her, despite her seven-year relationship with Donald Trump Jr. and her engagement to the president’s eldest son, according to insiders.

“Not everyone is shedding tears,” one source said.

The former diplomat is said to be especially hurt by the public rejection and by the lack of support from Trump’s female relatives, after years of appearing alongside the family at high-profile events.

First Lady Melania Trump, Trump’s daughters Ivanka and Tiffany, and daughter-in-law Lara Trump each had different relationships with Guilfoyle, Don Jr.’s former fiancée.

“They’ve all known Kimberly for years, but that doesn’t mean they all feel the same way about her,” an insider said.

“Ivanka has never been Kimberly’s biggest fan, Tiffany is largely indifferent, and Lara genuinely feels bad for her.”

Bettina Anderson, who recently married Don Jr., is said to be unmoved by the controversy. One source put it bluntly: “Kimberly simply isn’t someone Bettina spends any time thinking about.”

Melania Trump, meanwhile, reportedly kept her distance from Guilfoyle during the years she was dating Don Jr. Observers questioned why that relationship would change now.

“In the Trump family, there’s a world of difference between being welcomed at the family table for a time and having a permanent seat,” the insider said.

“Being the girlfriend doesn’t give you the same standing within the family.”

Trump’s remarks came shortly before Guilfoyle’s departure from her diplomatic post, delivering what sources described as a particularly painful blow to his son’s former fiancée.

Asked about their previously close relationship, the president told reporters: “No, she wasn’t a member of my family.”

“She, I guess, dated my son a long time ago.”

The comments reportedly cut deeply for Guilfoyle, a prominent MAGA supporter who spent years attending Trump family weddings, celebrating holidays and campaigning alongside them as though she were already part of the family.

 ‘That absolutely crushed Kimberly,’ a source told Naughty But Nice. 

‘She defended Donald, raised money, fought his battles and stood by him when others walked away. Now he’s treating her like some random girlfriend. Losing her job was humiliating. Being publicly disowned was heartbreaking.’

The cold shoulder from her ex-fiancé’s sisters has stung, too, according to insiders.

While none of the Trump women have commented publicly about Guilfoyle’s ongoing turmoil, sources said their reactions to her resignation were markedly different. 

‘Ivanka and Kimberly were never particularly warm toward each other,’ a source claimed. 

‘They have very different personalities, and while they could be perfectly cordial in public, that doesn’t mean there was a friendship behind the scenes. 

‘Ivanka has her own life, her own family and her own priorities,’ the insider added. ‘She’s not someone Kimberly would turn to for emotional support.’ 

Rumors of a tense relationship started swirling when Guilfoyle was still engaged to Ivanka’s brother. 

Ivanka made headlines when she cropped Guilfoyle out of a photograph featuring all of the Trump women at Tiffany’s lavish Mar-a-Lago wedding back in 2022. 

Sources close to the president’s eldest daughter insisted, at the time, that it was just a terrible mistake and not a deliberate snub.

Tiffany, meanwhile, is considerably less invested in the saga currently engulfing Guilfoyle. 

‘Tiffany doesn’t have strong feelings about Kimberly one way or the other,’ one source said. 

‘They spent time together at family events, but they weren’t especially close. Tiffany wishes her well and is happy to stay out of it.’

Eric Trump’s wife, Lara, is another story. 

‘Lara knows how hard it is to become part of the Trump family,’ an insider said. 

‘She married into it herself. She understands the scrutiny, the expectations and how difficult it can be to establish your own identity while everyone is watching.

‘Lara knows Kimberly worked incredibly hard for this family, and she doesn’t enjoy seeing her disappointed,’ the source added. 

‘She knows Kimberly devoted years to Don Jr. and the family. That history deserves respect.’

Guilfoyle started dating Don Jr in 2018 before he dropped to one knee on New Year’s Eve in 2020. They called it quits on their relationship after Our News Outlet reported that Don Jr had started romancing his now-wife, Anderson, in late 2024. 

In the wake of Guilfoyle’s downfall, sources close to Anderson said she was far too happy with her husband to be worried about his ex. 

‘She’s never felt the need to explain herself, defend herself, or engage in petty drama,’ the insider said. 

‘She’s always believed that time has a way of revealing the truth without having to say a word. There’s certainly a quiet sense of vindication in that, but she’s far too happy with her husband, her family, and the life they’re building to give any of this her attention.’ 

It was only hours after Our News Outlet reached out to Don Jr’s representatives about the nature of his relationship with the Palm Beach socialite that then-President-elect Trump abruptly announced he had nominated Guilfoyle to be the Greek ambassador. 

‘Kimberly wasn’t sent to Greece just because of her skills,’ a source said amid the current turmoil swirling around Guilfoyle. 

‘It also solved a complicated personal problem. Having her thousands of miles away worked for everyone.’ 

As the headlines about Guilfoyle’s conduct in Athens only continued to mount, sources say some Trump advisers had been wrangling to save her job – fearing she could return to the US with an axe to grind and spill Trump family secrets.  

Some even claimed she had a secret ‘burn book’ documenting the Trumps and is now ready to burn her bridges with the family following her dramatic fall from grace. 

‘Having her back in America would be a nightmare. Kimberly knows where the bodies are buried. She knows the people, the secrets, the fights, the relationships,’ one source said.

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

‘Kimberly knows everything. She was way inside that family and political operation for years,’ another insider chimed in.

‘Keeping Kimberly happy keeps Kimberly quiet.’

Our News Outlet has reached out to representatives for Ivanka Trump, Lara Trump, Tiffany Trump and Bettina Anderson.