On his show Tuesday night, Jimmy Kimmel actually expressed a bit of empathy for former Ambassador to Greece Kimberly Guilfoyle, who recently lost her job in the Trump administration thanks to an ethics scandal in which she apparently asked a Trump donor to pay off her $100,000 American Express bill.

“This president will not tolerate corruption in his administration unless he benefits directly from it,” Kimmel joked of President Donald Trump ousting Guilfoyle.

Notably, Guilfoyle was previously engaged to the president’s eldest son, Donald Trump Jr., and acted as a top Trump campaign surrogate and fundraiser during the lead-up to the 2020 presidential election.

“No, she wasn’t a member of my family,” Trump told the reporter. “She, I guess, dated my son a long time ago, but she wasn’t— no.”

Kimberly Guilfoyle speaks at the Republican National Convention in August 2020.

Bloomberg via Getty Images

After rolling a clip of Trump’s remarks about Guilfoyle, even Kimmel was a bit shocked by the president’s dismissiveness.

“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,” Kimmel continued. “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.”

Trump kisses Guilfoyle during a Greek Independence Day celebration in the East Room of the White House on March 26, 2026.

Bloomberg via Getty Images

Despite Guilfoyle’s alleged grift, Kimmel admitted that “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 [Trump] took billions from the Saudis. Melania gets big checks from Amazon. They’re all cashing in. All she did is 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.

Watch Kimmel’s take in the video below.