President Donald Trump offered an unusually candid window into his social philosophy last Friday, March 27, 2026, telling an audience of international investors that he prefers surrounding himself with people who lose — because successful people talk too much about themselves.
Trump, 79, was speaking at the Future Investment Initiative forum in Miami Beach, a summit run by Saudi Arabia’s Public Investment Fund, when he was asked about the qualities he values in leadership. His answer veered quickly into a meditation on the company he keeps.
“You got a lot of losers, losers,” Trump told the crowd. “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.” He went on to explain his distaste for high achievers, saying he dislikes listening to other people’s success stories and prefers an audience willing to listen to his own.
It was not clear who specifically Trump had in mind, and the White House did not respond to requests for clarification. But the remarks landed with particular resonance given the well-documented cast of characters who have cycled through the president’s inner circle over the years. His Mar-a-Lago estate in Palm Beach has long served as a hub for loyalists, donors, and influence-seekers eager to curry favor with whoever holds power in Washington.
Among the most scrutinized of Trump’s past associations is his years-long friendship with Jeffrey Epstein, the disgraced financier and convicted sex offender who died in a Manhattan jail cell in 2019 while awaiting federal sex trafficking charges. Epstein had described himself as Trump’s closest friend for over a decade. Also prominent in Trump’s history is Roy Cohn, the attorney who served as Sen. Joseph McCarthy’s aggressive right-hand man before becoming Trump’s personal fixer and lawyer in the 1980s. Cohn is widely credited with shaping Trump’s instinct to never admit fault and to attack relentlessly. He died of AIDS-related illness in 1986, having spent much of his career publicly opposing gay rights while living as a closeted gay man.
Trump’s current orbit includes Charles Kushner, a convicted felon and father-in-law to Ivanka Trump who now serves as the U.S. ambassador to France, as well as Special Envoy Steve Witkoff, a billionaire real estate developer who has known the president for more than four decades.
The Miami forum produced several other notable moments. At one point, Trump referred to the Strait of Hormuz as the “Strait of Trump” before catching himself — then insisting the slip was intentional. “The Fake News will say, ‘He accidentally said.’ No, there’s no accidents with me,” he told the crowd. He also invited the audience to ask him anything, adding: “You can talk sex.” On the subject of the ongoing U.S.-Iran conflict, which he launched in coordination with Israel on February 28, Trump declared that Iran was “on the run” from American forces.
Hours after those remarks, the Associated Press reported that at least 10 U.S. service members had been wounded at a military base in Saudi Arabia, with two listed in serious condition — a development that cast a sharper light on the president’s buoyant assessment of the war’s progress.