Jimmy Kimmel Humiliated Karoline Leavitt & Trump With This Messy Age-Gap Marriage Joke

Karoline Leavitt's 32-year age gap with her husband, Nicholas Riccio, has earned her scathing jabs from social media commentators and media personalities alike. On the rare occasions that the White House press secretary offers a glimpse into her private life with her hubby and their son, Niko, Instagram critics typically snark that they are unsure if Riccio is really her father or her grandfather. Although Leavitt may have grown used to such comments, she likely hadn't encountered a diss quite as brutal as Jimmy Kimmel's.

During a January 2025 episode of "Jimmy Kimmel Live!" the talk show host poked fun at their considerable age difference and her position in Donald Trump's administration in a singular sentence, quipping, "She's married to a much older real estate magnate, which, you know, in that case you're hired." Of course, the jab was also aimed at once real estate mogul Donald's 24-year age gap with Melania Trump. And Kimmel didn't stop there. 

He also joked that the former political aide "had promised a new and more circus-like atmosphere going forward" and proceeded to play a clip of her encouraging social media influencers to join the press briefing room after gaining the appropriate credentials. In May 2025, even Fox News issued a shady warning for Leavitt that put her age gap marriage on blast. Speaking on "Jesse Watters Primetime," comedian Matt Friend made a joke about the Former New England Patriots' coach's 49-year age gap with his girlfriend, saying, "By the way, Karoline Leavitt, stay away from Bill Belichick!" (via X, formerly known as Twitter). 

Karoline Leavitt made an embarrassing slip-up while discussing her massive relationship age gap with Nicholas Riccio. While appearing on "The Megyn Kelly Show" in March 2025, the youngest White House press secretary in U.S. history acknowledged that her 3-decade difference with Riccio was "atypical." Leavitt then attempted to prove that their differences didn't hinder their healthy relationship, proudly listing, "He is my greatest supporter, he's my best friend, and he's my rock." Unfortunately, it became obvious that even she couldn't ignore their glaring age difference sometimes, as the Trump staffer messed up by gushing, "He's the father of my child and he's the best dad I could ever ask for." Of course, she meant to appreciate his talents as a father to their child and not to her, but the damage was done. 

The comment was only made weirder by the fact that Leavitt's parents are actually closer in age to her husband than most people realize. The former political aide also didn't help her case by enthusing about how Riccio had supported her career after building his own since her compliment, again, seemed more appropriate for a father figure. Even worse, Leavitt once accidentally revealed that the most important man in her life was not her husband. While giving influencer Kate Mackz an office tour in May 2025, the White House staffer revealed that she had several important photos up on her wall — including a snap of her son and a framed pic of herself proudly posing with Donald Trump. However, one of the many red flags in Leavitt and Riccio's marriage was that his image wasn't on the wall.