Jimmy Kimmel posing on the red carpet.© Ethan Miller/Getty Images

Many have had a field day roasting Karoline Leavitt’s massive age gap relationship, and Jimmy Kimmel is no exception. In fact, just over a week into Leavitt’s new gig as Donald Trump’s press secretary, the comedian hinted that Leavitt being involved with a much older man in real estate may have prompted the president to see her as the perfect pick for the job. Oop.

Speaking during the January 28, 2025, episode of “Jimmy Kimmel Live,” the host noted the fact that Leavitt was the youngest person to have ever held the position of press secretary at the White House. That is pretty impressive, in itself. However, that’s not to say Kimmel was complimentary. He followed that up with, “She’s married to a much older real estate magnate, which, you know, in that case you’re hired.” A barb that undermined Leavitt’s eligibility for the role, poked fun at Leavitt and Nicholas Riccio’s 32-year (yes, really) age gap, and made a joke about Trump’s “The Apprentice” days (and his own track record of age-gap relationships) in just one sentence. Like we said, oop. 

However, whether or not one agrees with Leavitt’s politics and approach — which has included inviting content creators and podcasters to apply for White House press passes, and which Kimmel also roasted — she does have some impressive credentials. In addition to the executive director of the New Hampshire Institute of Politics at her alma mater telling CBS News she had been one of the most impressive students he’d ever met, she ran for Congress in 2022, aged just 25. She also worked for Trump’s first administration as an assistant press secretary to Kayleigh McEnany. As such, she’s not exactly unqualified, regardless of who she’s married to (and it’s a little sexist to suggest otherwise).

Karoline Was Already In Politics When She Met Her Husband

Karoline Leavitt speaking to press at The White House.© Andrew Harnik/Getty Images

As funny as it is to draw parallels between Karoline Leavitt’s marriage and Donald Trump’s (need we remind anyone, the real estate mogul is stunningly closer in age to Melania Trump’s father Victor Knavs than he is to her), it’s also important to keep in mind the fact that Leavitt was making moves in Trumpland before she met her much-older (and much-roasted) husband.

In addition to the fact that Leavitt had already worked as Kayleigh McEnany’s assistant at 23, she also started campaigning for Congress before knowing Nicholas Riccio. As she shared in an interview on “The Megyn Kelly Show,” it was during her campaign that they first got to know one another. “I met my husband during my congressional campaign. A mutual friend of ours hosted an event at a restaurant he owns up in New Hampshire and invited my husband … We met, we were acquainted as friends, and then we fell in love,” she recounted. Pushed by Kelly as to whether there was any weirdness over their age difference, Leavitt smiled, “Yes of course!” Even so, she went on to gush over his supportiveness … and in so doing she shared a line we kind of wish she’d said sooner, if only for Jimmy Kimmel to poke fun at that rather than insinuate that she was hired based on who her husband was.

“I say, ‘I walked into your life and it’s been a circus ever since,'” she joked to Kelly. As for Kimmel, he’d joked on his show, “Leavitt is now the ringleader at the White House, where she promised a new and more circus-like atmosphere going forward.” Ah, what could have been.