Karoline Leavitt's Latest Trump Photo Backfires As People Side-Eye Their Cozy Relationship

Karoline Leavitt and Donald Trump appear to have a pretty tight connection. An April video tour of Leavitt's office showcased a prominent portrait of Trump, revealing his high status in her life. In July, Leavitt accompanied the president to Scotland, tagging along as Trump seemingly cheated at golf. To document the trip, she posted a photo of the two of them on Instagram. Leavitt's shown her fondness for Trump in pics before, and this time she cozied up to Trump's shoulder while they beamed at the camera. Another shot in the same carousel showed the pair leaning towards each other, deep in conversation as Trump drove their golf cart.

Not surprisingly, some commenters took the opportunity to swing off topic and reference the drama surrounding Trump and the Epstein files. While a few expressed admiration of Leavitt and Trump's bond, many others made snarky remarks. "Looks like you like him more than Melania," commented one. Another made a shady reference to drama from Bill Clinton's presidency, writing, "Melania come get your husband from Monica Lewinsky."

As White House Press Secretary, it's part of Leavitt's job to travel with the president. When sharing behind-the-scenes details about their dynamic, however, Leavitt mentioned a nickname some would find off-putting. "Every time every time before I take the podium, he always says, 'Just have fun, honey,'" she divulged to the "Ruthless" podcast. Although this moniker is out of place in a professional conversation, Leavitt's casual inclusion of it seems to indicate she isn't bothered.

Earlier in July, Karoline Leavitt pivoted into mom life, and it appeared she might be experiencing burnout in her stressful job as White House press secretary. However, Leavitt's recent pics with Donald Trump seem to indicate their chummy connection is going strong. Leavitt's fandom for Trump developed when she was in college. Beyond voting for him when she was 18, Leavitt was busy defending him in her college newspaper. Eager to work with him, Leavitt was also motivated to seek out a White House internship. Eventually she worked even closer with the president as assistant press secretary.

After Trump lost the 2020 election and they went their separate ways, Leavitt reconnected with him in 2022 during her congressional campaign. While they weren't buddies back then, less than two years later, their friendship really took off after Leavitt became Trump's campaign press secretary. After Leavitt's son was born in July 2024, she was delighted that Trump took time offer his best wishes via phone.

In a March interview with The Daily Signal, Leavitt mentioned how Trump had championed her becoming press secretary at such a young age. He'd noted their common ground in both being very young and working in high-profile careers. Leavitt also took her Trump fangirling to new heights. "A great storyteller. I've had many dinners sitting with him and just listening to his life story," she gushed. "He's hilarious. Literally one of the funniest people I've ever met."