Red Flags In Karoline Leavitt And Donald Trump's Working Relationship We Can't Ignore

The White House Press Secretary Karoline Leavitt has a unique working relationship with President Donald Trump. The two appear to be very close, with Leavitt going to bat for Trump with the press. For example, recall the contentious moment when Leavitt got into a text fight with a journalist who asked if Trump understood the significance of choosing Budapest as a location to meet Russian President Vladimir Putin. When the journalist asked who chose the spot, Leavitt wrote back, "Your mom did," followed by a pretty heated argument. She's willing to fight for Trump, but their curiously close relationship has also led to rumors and jokes on the internet that it all isn't as it seems, with many hinting that there's a romantic undercurrent to their professional collaboration.

They've been plagued by affair rumors, exacerbated by the fact that Leavitt has a 32 year age gap with her husband, and Trump has been involved in several cheating scandals. After all, there have been several occasions when Donald and Melania Trump sent divorce rumors flying. To make matters worse, Trump and Leavitt have also spoken about each other in strange ways, using language that seems a little too close and intimate. They're also photographed together quite often, smiling and close, with their spouses nowhere in sight.

Karoline Leavitt can't escape rumors about her love life, and things got really out of control after she accompanied President Donald Trump on a trip to Scotland in July 2025. She posted a carousel of photos on Instagram, sharing pictures of the two in action — as well as taking some R&R on the golf course. The two sat in on meetings together, and rode in a golf cart side by side. In fact, it seems like they spent a good chunk of the trip in each other's company.

Unsurprisingly, people on the internet had a lot to say about it, throwing around remarks that the two were having an affair. Referring to Donald and Melania Trump's child, Barron Trump, someone commented: "[Barron's] future stepmom. Does Melania know?" Another commenter referred to the scandal that marred President Bill Clinton's era: "Monica Lewinsky 2.0? Who knows?" "Sugar Daddy and his sweet lil Girl," another said. The comments showed an undercurrent of mistrust around Trump and Leavitt's working relationship.

Donald Trump didn't help the situation when he made some inappropriate comments about Karoline Leavitt's lips. During a flight on Air Force One in October 2025, Trump spoke to reporters about his unyielding loyalty to Leavitt. This all started because one reporter asked if the press secretary would ever be replaced.

Trump said no, and gave his reasons. "[Leavitt'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," he said (via People). "I don't think anybody has ever had a better press secretary than Karoline. She's been amazing," Trump added. Unsurprisingly, people were very uncomfortable with the way Trump spoke about Leavitt. "In the public sector, this is called 'sexual harassment' and a 'hostile working environment' — Trump's comments are sick and twisted!" a viewer commented on X. "This is just so creepy," another netizen said. "Who talks like this about their employees?!? Call HR. WTF," a third chimed in.

While Donald Trump made questionable comments in praise of Karoline Leavitt's physical appearance, the press secretary shows her own loyalty to Trump through her social media. A casual scroll through Leavitt's Instagram page is overtaken by photos of Trump and their shared White House world. There are hardly any photos of Leavitt's husband, Nicholas Riccio.

It's not just that Leavitt primarily posts Trump. It's also the fact that the captions for her posts are so full of praise and adoration. Sure, it's nice to feel a sense of pride in one's work, but Leavitt's posts read as heavy fangirling with a touch of flirtation. In one photo posted in December 2024 of Leavitt with Trump, she wrote: "The boss." In another post of Leavitt whispering something to the president in the Oval Office, she wrote: "Briefing the boss." In another photo of Leavitt watching Trump speak to the press, she wrote: "Most transparent President in history." While these aren't the most outrageous things to say, Leavitt is talking about her employer and place of work, not running a fan account. Trump might have said some curious things about Leavitt out loud, but Leavitt isn't shy about lavishing her admiration for Trump all over the internet.

Karoline Leavitt returned to work four days after giving birth to her son. She delivered her baby on July 10, 2024, and her maternity leave was cut short because of the assassination attempt made on Donald Trump on July 13, 2024, when he was speaking at an open-air rally near Butler, Pennsylvania. Leavitt discussed the experience with The Conservateur. "I had just brought my newborn, my three-day-old baby home from the hospital. And I said, 'I'm going to turn on the television and watch the rally today,'" she explained.

Leavitt said that she saw the shooting, and made a decision there to return to her job. "I looked at my husband and said, 'Looks like I'm going back to work,'" Leavitt said. So four days after giving birth to her son, Leavitt made a TV appearance. "I felt compelled to be present in this historic moment," Leavitt added. "The president literally put his life on the line to win this election. The least I could do is get back to work quickly." It was a huge decision for Leavitt to make. With no interest in mom-shaming, it's important to note that the National Library of Medicine states that ideally, women take a minimum of 12 weeks off after giving birth for their physical wellbeing. The fact that Leavitt only gave herself four days shows a substantial degree of dedication to her job — as well as the president.

The fact that Karoline Leavitt's husband, Nicholas Riccio, is 32 years older than her doesn't help the red flags in her working relationship with Donald Trump. Add to this fire the fact that Riccio is rarely seen with Leavitt. This huge age gap, along with Trump's notorious cheating record, makes their working relationship ripe for jabs and comments from outsiders.

People online often make hints about Leavitt's penchant for older men, assuming that this interest extends to Trump, as well. "Karoline like them old," someone commented on her Instagram. Another made a jab when Leavitt shared photos next to Trump: "Can't tell if that's her husband or not," they wrote. Ouch. While Leavitt hasn't given these jokes the time of day, the age gap in her marriage does take a toll on her professional life. She's often criticized for wearing dowdy, aging outfits. In fact, Leavitt's worst outfits all have one thing in common, and it makes so much sense: she's dressing for her husband's age bracket, not her own. So while the jabs about red flags in her working relationship with Trump go unaddressed, Leavitt's marriage is stirring the pot in its own way.