A single glance has ignited a firestorm of speculation across social media, with users drawing uncomfortable parallels between President Donald Trump’s relationship with his 27-year-old press secretary and one of the most infamous political scandals in American history.
The controversy erupted when the Jerry Can Crew posted a clip from Trump and Karoline Leavitt’s July 15 emergency press conference on the North Lawn, setting the footage to Mariah Carey’s “Heartbreaker” with the eyebrow-raising tagline “Trump Interview with a Side of Romance.”
The 15-minute impromptu session, which covered weighty topics including Trump’s warnings to Russia, the Epstein files, and New York City’s mayoral race, took on an entirely different tone in the edited clip.
Viewers fixated on a particular moment where Leavitt appeared to gaze at the 79-year-old president with what many interpreted as more than professional admiration. Her slight smile and the way her eyes seemed to follow Trump’s movements sparked immediate commentary across social platforms.
The online reaction was swift and unforgiving when Jerry Can Crew posted it.
“She’s looking at him like ‘ohh, daddy’!” one user commented, while another drew direct historical parallels: “Total Monica in the White House we all know how you got that job sweetheart!”
The comparisons to former President Bill Clinton’s infamous affair dominated the discourse, with one particularly pointed observation stating, “I swear she looks at him like Monica looked at Clinton,” followed by another user’s cheeky advice: “Monica Lewinsky vibes …..keep that dress,” referencing the garment the former intern kept after one of their romantic liaisons.
Perhaps most tellingly, one commenter noted the age dynamics at play: “Her husband’s same age or close to it lol,” highlighting the 52-year age gap between Trump and his 27-year-old press secretary, who recently married real estate developer Nicholas Riccio just days before Trump’s second inauguration.
The speculation gains additional context when viewed against Trump’s well-documented history of controversial comments about women.
During the recent Newsmax interview with host Rob Finnerty, Trump’s response to questions about Leavitt’s professional performance took an unsettling detour into physical descriptions.
“She’s become a star. It’s that face, it’s that brain, it’s those lips, the way they move, they move like she’s a machine gun,” Trump said, lingering notably on the word “lips” in a manner that made many viewers uncomfortable.
This pattern of behavior extends far beyond his current press secretary.
Trump’s inappropriate comments about women date back decades, including a particularly disturbing 2007 Learning Annex event where he cuddled with a female audience member on stage while reminiscing about hiring a “beautiful girl who was 17 or 18” as a waitress simply because of her appearance. During that same event, he compared his attraction to women to alcoholism, telling the crowd that having an attractive woman work on his plane would be “like a death wish for me.”
Even more troubling are the documented inappropriate comments Trump has made about his own daughters over the years.
Former Trump administration official Miles Taylor alleged in a 2023 book that Trump made lewd comments about daughter Ivanka’s appearance in front of White House staff, remarks so shocking that then-chief of staff John Kelly reportedly had to remind Trump that Ivanka was his daughter.
The controversy has even caught the attention of popular culture.
South Park’s Season 27 premiere, “Sermon on the Mount,” satirized the Trump administration with cartoon Trump and Leavitt. Scenes showed Trump getting updates on Canadian tariffs and supporter backlash. The satire stirred enough controversy that White House Assistant Press Secretary Taylor Rogers dismissed the show’s creators as lacking “authentic or original content.”
For Leavitt, who holds the distinction of being the youngest person ever to serve as White House press secretary, the scrutiny comes at a challenging time. Beyond navigating the intense media attention, she’s dealing with significant financial pressures from her failed 2022 congressional campaign, with her campaign owing more than $326,000 to creditors and currently under Federal Election Commission audit for illegal campaign contributions.
While chatter swirls about Trump and Leavitt’s dynamic, one thing is certain — in politics, even a simple smile from a young staffer to her boss can spark a storm of ugly jokes and speculation.
The Saint Anselm grad’s fleeting glance may have been harmless, but given the president’s history of womanizing and objectifying, and the White House’s long trail of scandals, the public is bound to think the worst.
And once again, Monica Lewinsky’s name gets dragged back into the fray, despite her decades away from Washington and her attempts to change the narrative around her life.
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