Jimmy Kimmel really crossed the line and insulted Karoline Leavitt and her husband. — In an explosive live TV moment, Jimmy Kimmel took things too far when he questioned Karoline Leavitt’s integrity with a brutal remark.

Both comedians and critics have taken an interest in Karoline Leavitt’s relationship with her much older husband, and Jimmy Kimmel seized the opportunity to weigh in.

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The late-night host made a scathing joke implying that Leavitt’s personal life might have affected her appointment to the position of press secretary for Donald Trump just a few days after she started working there.

During the January 28, 2025, episode of “Jimmy Kimmel Live,” Kimmel recognized that Leavitt had achieved a noteworthy feat by becoming the youngest person to hold the position of White House press secretary. The recognition, though, soon devolved into parody.

“She’s married to a much older real estate tycoon, so you’re hired in that case,” he joked. Kimmel was able to make fun of Leavitt’s credentials and the 32-year age gap between her and her husband, Nicholas Riccio, with that.

Regardless of one’s political stance, Karoline Leavitt’s resume demonstrates some noteworthy accomplishments. She was one of the most remarkable students he had ever met, according to the executive director of her alma mater’s New Hampshire Institute of Politics, who spoke to CBS News.

She worked as an assistant press secretary for Kayleigh McEnany during Trump’s first administration before running for Congress in 2022 at the age of just 25. Regardless of her marital status, it’s difficult to argue she’s unqualified given her experience, and suggesting otherwise comes across as blatantly sexist.

When Leavitt met her husband, she was already involved in politics.

Given the similar age gap between the president and his wife, it’s easy to compare Karoline Leavitt’s marriage to Donald Trump’s, but it’s crucial to remember that Leavitt had established a political career long before she met her older husband, Nicholas Riccio.

Before ever meeting Riccio, at the age of 23, she began her congressional campaign while working as an assistant to Trump press secretary Kayleigh McEnany. They met at a campaign event at Riccio’s restaurant in New Hampshire, which was organized by a mutual friend, as she revealed on “The Megyn Kelly Show.” “After meeting and becoming friends, we fell in love,” she remarked.

In response to a question concerning their age difference, Leavitt said, “Yes, of course!” but also commended Riccio’s assistance, joking, “I walked into your life and it’s been a circus ever since.” The circus theme is still relevant, albeit in different contexts, as evidenced by Jimmy Kimmel’s ironic joke that Leavitt was “now the ringleader at the White House.”