Trump’s Devastating Kimberly Guilfoyle Diss Floors Kimmel
The late-night host had a surprising defense for Trump’s fired devotee.
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.
Kimberly and Don Jr. called it quits in 2024, after a nearly three-year engagement.
CARLO ALLEGRI/REUTERS
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.
Donald Trump and Kimberly Guilfoyle bow their heads in prayer during a Greek Independence Day celebration at the White House on March 26, 2026.
JIM WATSON/AFP via Getty Images
“Not only did she date your son for six years, they were engaged to be married,” Kimmel responded incredulously.
Get the best of Obsessed delivered right to your inbox
By clicking “SUBSCRIBE” you agree to our Terms of Use and Privacy Policy.
“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.
Donald Trump Jr. and Kimberly Guilfoyle were together for years.
JIM BOURG/REUTERS
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.”
Kimberly Guilfoyle's attempted grift angered the president.
Aurore Marechal/Getty Images
“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.
Obsessed with pop culture and entertainment? Follow us on Substack and YouTube for even more coverage.
Got a tip? Send it to The Daily Beast here.
Register below to read this article for free or subscribe
to unlock unlimited access to The Daily Beast.
Monthly
$1
First month then $5.99/month
Annual
$35
First year then $59.99/year
Premium
$79
First year then $119.99/year
*Substack access provided by the next business day, using your subscription email. Choosing the Premium plan constitutes your permission to share your subscription email with Substack and your agreement to Substack’s Privacy Policy.
Already have an account? Sign In
Looks like you already have a subscription!
You're all set!
Thanks for subscribing.
Sign in or create an account
Login dialog
Loading comments…