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Karoline Leavitt trolled by Donald Trump as he makes brutal ‘losers’ dig live on air

- March 29, 2026


Karoline Leavitt is just one of many Republicans who found themselves being humiliated by President Donald Trump as he said he likes to ‘hang around with losers’

It’s not the first time Karoline Leavitt has been ridiculed by Donald Trump – and it likely won’t be the last.

The White House press secretary, 28, was among a number of Republicans who found themselves being inadvertently called out by the president. The 79-year-old addressed attendees at the Future Investment Initiative in Miami on Friday, March 27, as he boasted about how he likes to surround himself with “losers.”

At the event, Trump was asked, “What is missing in leadership?” His response aired live on C-SPAN as he said, “Well it’s winning, you gotta win. You know, I’ve watched a lot of people, leaders, great leaders. And you know, the one thing about sports is you break it down into two hour periods, something nice.” Trump also bragged about how open he thinks he is with the media.

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The president continued, “You don’t have to wait a lifetime to find out if somebody’s a winner or a loser. You got a lot of losers, mostly losers, fortunately. It’s a good thing they have a lot of losers.

“I always like to hang around with losers actually, because it makes me feel better. I hate guys that are very, very successful and you have to listen to their success stories. I like people that like to listen to my success.”

A clip of the C-SPAN broadcast was shared on X, where viewers were quick to point out Trump appeared to mock those close to him, including Leavitt. “This is the most Trump quote of all time. It sums him up perfectly. It also explains his cabinet,” one person joked.

Another suggested, “He’s literally telling the world he surrounds himself with incompetent people — because they stay loyal to him, even as he ruins the country,” as a third viewer laughed, “Losers LOVE Losers ..that explains his Administration.”

“Trump just admitted—out loud, on camera—that he deliberately surrounds himself with losers because successful people make him feel small. He can’t stand hearing their stories; he only wants an audience for his own,” someone else fumed.

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They added, “This isn’t leadership. It’s the textbook confession of a malignant narcissist too insecure to grow, too fragile to compete, and too childish to lead. Pathetic.” A fifth person posted, “The way I just snort laughed at Trump calling everyone in his orbit losers. Pappy dementia is in rare form tonight.” Other viewers shared pictures of Republicans, including Leavitt, to suggest these are the “losers” Trump was referring to.

It’s not the first time Trump has drawn attention for his comments about Leavitt. In December, the 79-year-old raised eyebrows for comments he made about her appearance.

Speaking at a rally in Pennsylvania, the president was supposed to speak about the economy. He seemed to get distracted by Leavitt, however, as he turned his attention to her “beautiful face and those lips that don’t stop.”

In October, he also spoke about Leavitt’s lips while speaking to press on Air Force One. When asked about if Leavitt will ever be replaced, Trump said, “It’ll never happen. That face…and those lips. They move like a machine gun, right?”



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