Karoline Leavitt Branded Trump As The ‘Coolest Boss Ever’ And Instantly Regretted It

Karoline Leavitt had some surprising praise for her boss, the president.


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Effusive praise for President Donald Trump, from White House Press Secretary Karoline Leavitt, is far from a rare occurrence. But Leavitt went a bit over the top this week, even by her standards.

Leavitt posted a video to X on Monday of Trump signing hats and other items at the U.S. Open in New York on Sunday. It included the caption “The People’s President and the coolest boss ever. Signing hats for fans at the #USOpen,” followed by smiling-face and tennis ball emojis. 

Social media users, however, let Leavitt know what they thought of her video.

Leavitt was mocked for something else this week: Her shifting explanations about the Jeffrey Epstein “birthday book,” and Trump’s letter that was included in it. The Wall Street Journal had reported on the existence of the book and the letter earlier this summer, at which point Trump and the White House denied that the letter was real, and went so far as to sue the Wall Street Journal, its owner Rupert Murdoch, and the reporters involved.

This week, Epstein’s estate made the book available, it was released by Congress, and it was exactly as the Journal described it. But Leavitt has continued to maintain the line that the letter from Trump was not real.

“The president did not write this letter. He did not sign this letter,” said Leavitt this week, per Politico.

Photo courtesy of the Political Tribune media library. 


Stephen Silver
Stephen Silver is an award-winning journalist, essayist and film critic, and contributor to the Philadelphia Inquirer, the Jewish Telegraphic Agency, Broad Street Review and Splice Today. The co-founder of the Philadelphia Film Critics Circle, Stephen lives in suburban Philadelphia with his wife and two sons. Stephen has authored thousands of articles that focus on politics, technology, and the economy.

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