WASHINGTON, D.C. – In what critics are calling one of the most “bizarre” and “creepy” weeks in recent political history, a storm has erupted surrounding President Donald Trump and his 27-year-old Press Secretary, Karoline Leavitt. The controversy began at 30,000 feet aboard Air Force One and has since spiraled into a late-night television war, with Jimmy Kimmel exposing uncomfortable truths, alleged fabrications, and a personal life that has left the public stunned.

The “Machine Gun” Lips Comment

The incident that sparked the firestorm occurred during a gaggle with reporters on Air Force One following Trump’s recent trip to the Middle East. While discussing Leavitt’s performance as the youngest Press Secretary in history, the President didn’t focus on her policy knowledge or communication skills. Instead, he fixated on her physical appearance in a way that reportedly silenced the room.

“That face and those lips,” Trump told reporters, according to witnesses and later reiterated in interviews. “They move like a machine gun, right? Get it out like, immediately.”

The comment, intended as praise for her rapid-fire defense of his policies, landed with a “thud” for many observers. Late-night host Jimmy Kimmel, known for his relentless roasting of the former President, seized on the moment, labeling it “the creepiest moment in presidential history.”

“You know that feeling when someone says something so inappropriate, so jaw-droppingly wrong, that the entire room goes silent?” Kimmel asked his audience. “He’s openly musing about this woman’s lips… I feel like if I live to be a thousand years old, I won’t ever see anything as weird as this man running a country.”

For critics, the comment was a disturbing reminder of Trump’s history of objectifying remarks about women in his orbit. But for Kimmel, it was just the opening salvo in a much broader takedown of Leavitt’s sudden rise to power.

The 32-Year Age Gap

During his monologue, Kimmel pivoted from the “lips” controversy to a detail about Leavitt’s personal life that has largely flown under the radar: her marriage to Nicholas Riccio, a real estate developer 32 years her senior.

Leavitt, 27, married Riccio, roughly 60, in January 2025, just days before the inauguration. Kimmel didn’t pull any punches regarding the dynamic, pointing out the uncanny parallel between Trump’s own marriage and that of his spokesperson.

“She’s 27 years old… she’s married to a much older real estate magnate,” Kimmel quipped. “Which, you know, in that case: You’re hired!”

Kimmel highlighted the irony of Trump, who is 24 years older than Melania, hiring a Press Secretary in an almost identical situation. “It’s like he’s building an administration based on his own creepy preferences,” Kimmel joked, sending the audience into hysterics. The host even flagged a “Freudian slip” from a past Leavitt interview where she described her husband as “the best dad I could ever ask for”—before quickly clarifying she meant “dad for their son.”

The age gap has become a hot topic on social media, with internet sleuths noting that Riccio is closer in age to Leavitt’s parents than to her. Reports even surfaced that when influencers toured her office, a framed photo of Trump was prominently displayed, while photos of her husband were notably absent—a detail that has only fueled the “cult of personality” narrative surrounding the administration.

The War on Reality: Fake Videos and Fabricated Deployments

Beyond the personal jabs, the controversy has highlighted a more dangerous trend: the spread of verifiable lies and “fanfiction” propaganda.

Kimmel exposed a bizarre online phenomenon where Trump supporters have been circulating videos with titles like “Karoline Leavitt Kicked Off Jimmy Kimmel’s Show After Fiery Confrontation.” These videos, often garnering hundreds of thousands of views, depict a debate that never actually happened.

“One problem,” Kimmel noted dryly. “It never happened. Leavitt has never appeared on Jimmy Kimmel Live. There’s no footage, no guest list appearance, nothing.”

The host argued that these “deep fake” style narratives are a sign of desperation. “They literally invented a confrontation that never occurred. Think about how pathetic that is. They can’t actually defend Trump’s creepy behavior… so they create fantasy scenarios where she wins arguments that never happened.”

But the fabrications aren’t limited to YouTube titles. The article notes that Leavitt herself has been caught in significant falsehoods from the podium. In her very first press briefing, she allegedly claimed that Trump had deployed the U.S. military to California to “turn on the water” during a wildfire crisis.

“This is not liberal versus conservative,” Kimmel stated, dismantling the claim. “It didn’t happen. The military did not enter California. There was no ‘water to turn on.’ It was a complete fabrication, and she delivered it like it was fact.”

A “New Normal”?

The cumulative effect of these scandals—the “creepy” comments, the normalizing of massive age gaps in power dynamics, and the casual use of disinformation—paints a chaotic picture of the current White House.

Analysts suggest that the strategy is to flood the zone with so much noise that the public becomes numb. Leavitt’s recent announcement that she would prioritize press credentials for “content creators,” “podcasters,” and “influencers” over traditional journalists seems to confirm this shift. By replacing adversarial reporters with friendly internet personalities who “worship” the President, the administration aims to curate a reality where “machine gun lips” are a compliment and fake military operations are accepted as truth.

As Kimmel concluded in his viral segment, the danger isn’t just the jokes—it’s what lies beneath them. “We’ve become so numb to the dysfunction that a President fantasizing about his employee’s lips barely makes headlines,” he warned. “But if we forget, if we let them normalize this insanity, then they win.”

For now, the war between the late-night host and the White House press room shows no signs of cooling down. But one thing is certain: with every “bizarre” comment aboard Air Force One, the world is watching closely, wondering just how much stranger things can get.