Karoline Leavitt speaks to reporters following a flight on Marine One (2025)© Andrew Leyden/Shutterstock

Comedian Matt Friend popped onto Fox News to sit down with personality Jesse Watters to combine some roasting with some impressions, according to his own Instagram post. However, the camaraderie veered toward the absurd when Friend clearly made Watters uncomfortable with a throwaway joke at the expense of White House Press Secretary Karoline Leavitt and her much older husband Nicholas Riccio. As he was signing off, Friend tossed out, “By the way, Karoline Leavitt, stay away from Bill Belichick.” To which Watters quickly said, “We’ve gotta go.”

What Friend was slyly poking at was the rather aggressive age gap relationship between Belichick and girlfriend Jordon Hudson and how this mirrors the marriage Leavitt finds herself in. Of course, every time Leavitt tries to show off her older husband, she gets roasted for it, which most likely gave Friend the courage to make such a joke on air. While Leavitt often wears outdated clothing, possibly in an attempt to distract from how much younger she is than Riccio, it might not be enough to convince the masses that her relationship is not a joke.

Read more: Once Famous Trump Supporters Who Now Can’t Stand Him

Karoline Leavitt Isn’t Outrunning The Jordon Hudson Comparison

Split image of Karoline Leavitt and Jordon Hudson© Joshua Sukoff/Shutterstock & Aaron J. Thornton/Getty

While Karoline Leavitt and her husband Nicholas Riccio live a lavish life together, they can’t escape constant nagging around their multi-decade age gap. With Riccio closer in age to Leavitt’s parents than his wife, there’s been a deluge of criticism at the awkward couple ever since Leavitt snagged her role in President Donald Trump’s second administration. When comedian Matt Friend made the comparison to the weird relationship between Bill Belichick and Jordon Hudson, many seemed to agree he was onto something.

The previous Patriots coach and Hudson have a 49-year age gap — a bit longer than Leavitt and Riccio’s 32-year spread. One commenter on X, formerly Twitter, noted that Leavitt “already has her own ‘Belichick.'” Another noted that Riccio “is pretty close to [Bill Belichick’s] age.” Still another made the astute observation that Belichick’s “the right age for her, apparently.”

For her part, Leavitt has hinted that she might be embarrassed by her much older husband, but it seems as if they’re in it for the long haul — for now. Considering they share a young son and only just got married to each other, the red flags that Leavitt and Riccio won’t last will have to continue to add up.