Trump Unleashes Scathing Critique of 'Loser' Mar-a-Lago Loyalists

The former president lashed out at his closest associates, revealing his apparent insecurity around successful people.

Mar. 28, 2026 at 4:51pm

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In a candid speech at an investor forum in Miami, former President Donald Trump offered a glimpse into his personal relationships, criticizing members of his inner circle as 'losers' and expressing a preference for surrounding himself with less successful people to make himself feel better. Trump's remarks touched on his long-standing associations with controversial figures like Jeffrey Epstein and Roy Cohn, as well as current allies such as Charles Kushner and Steve Witkoff.

Why it matters

Trump's comments provide a rare window into his psyche, suggesting an underlying insecurity that drives him to surround himself with loyalists rather than high-achievers. This insight into his leadership style and interpersonal dynamics could have broader implications for understanding his political motivations and the dynamics within his inner circle.

The details

During the speech, Trump lamented about having to 'listen to [the] success stories' of 'very, very successful' people, saying 'I like people that like to listen to my success.' He also referred to some of his closest associates as 'losers,' though he did not specify who he was talking about. Trump's relationships with controversial figures like Jeffrey Epstein and Roy Cohn have been well-documented, and he currently counts Charles Kushner and Steve Witkoff among his close allies.

  • Trump delivered the remarks on Friday, March 28, 2026 at an investor forum in Miami.

The players

Donald Trump

The 79-year-old former president of the United States, known for his brash and divisive leadership style.

Jeffrey Epstein

The disgraced financier and convicted sex offender who once described himself as Trump's 'closest friend.'

Roy Cohn

Trump's personal fixer and lawyer, also known as Senator Joseph McCarthy's sinister sidekick and a ruthless prosecutor who is credited with shaping Trump's 'never-admit-fault' approach.

Charles Kushner

A convicted felon and the father-in-law of Ivanka Trump, who serves as U.S. ambassador to France.

Steve Witkoff

A billionaire real estate developer who has known Trump for more than four decades and serves as a special envoy.

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What they’re saying

“'You got a lot of losers, losers. Fortunately, it's a good thing to have a lot of losers. I always like to hang around with losers, actually, because it makes me feel better.'”

— Donald Trump, Former President

“'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.'”

— Donald Trump, Former President

The takeaway

Trump's scathing critique of his closest associates reveals an underlying insecurity that appears to drive his leadership style and interpersonal dynamics. His preference for surrounding himself with 'losers' rather than high-achievers sheds light on his motivations and the power dynamics within his inner circle.