Donald Trump has not only let go of Kimberly Guilfoyle after her “tacky” scandal, but also publicly dissed his ousted ambassador to Greece.
Jimmy Kimmel was floored by Trump’s brutal parting words to Guilfoyle, who was engaged to the president’s eldest son, Donald Trump Jr., for years.
After firing Guilfoyle, Trump was asked by reporters about this past relationship. “No, she wasn’t a member of my family. She, I guess, dated my son a long time ago,” he told the press.
Guilfoyle, 57, began dating Don Jr., 48, in 2018. They got engaged in 2020 but never went through with their marriage. Don Jr. began dating socialite and model Bettina Anderson in 2024, and they married in 2026.
Despite the years-long partnership between Guilfoyle and his son, Trump was quick to dismiss her role in the wider Trump clan.
“Not only did she date your son for six years, they were engaged to be married,” Kimmel responded incredulously.
“They broke up two years ago, and you sent her to Greece to get rid of her. Poor Kimberly Guilfoyle. You know, she’s the first woman ever to get dumped by Donald Trump Jr. and Donald Trump. She got the double Trump dump, and that’s got to hurt,” he continued.
Kimmel roasted the MAGA stalwart for the scandal that became the nail in her coffin. Last week, Guilfoyle was exposed for begging a donor to pay off her $100,000 credit card bill just days before she was sworn in as ambassador, adding to other eyebrow-raising controversies. Guilfoyle was subsequently fired on live television during Trump’s new press secretary’s White House briefing.
She may have a laundry list of grifts, but Kimmel said “you almost have to feel bad for her.”
“Donald Trump himself took a $400 million plane from Qatar. He’s made billions of dollars in crypto. His sons have made billions in crypto. Jared Kushner and Ivanka took billions from the Saudis. Melania gets big checks from Amazon. They’re all cashing in. All she did was ask a donor to pay off her credit card bill. She’s like, ‘What did I do wrong?’” he joked.
“But that’s how it goes with these people. They fall by the wayside while the annoying orange marches on,” Kimmel concluded.
