Trump told a room full of investors he likes hanging around losers, but that wasn’t the most eyebrow-raising thing he said all speech

President Donald Trump made a surprising comment at the Future Investment Initiative in Miami, telling a room full of investors that he likes to “hang around with losers” because it “makes me feel better.” The event gave Trump a wide platform to speak freely, and he certainly used it.

During a Q&A session after his main speech, Trump was asked what leadership trait the world is currently missing. His answer was direct: “Well, it’s winning.” He compared it to sports, saying it’s easy to spot a winner from a loser, and added, “You got a lot of losers, mostly losers, fortunately.” He then said, “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.” The audience laughed at the remark.

According to Mediaite, Trump followed up by saying, “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.” He briefly said he was joking, “I’m only kidding, I wanna say that,” but then pulled back on that, adding, “Eh, sort of.”

Trump calling Soleimani a ‘mad genius’ was arguably the most striking moment of the event

Beyond his comments on winners and losers, Trump also called Iranian military official Qasem Soleimani a “great leader” and a “mad genius” during the speech. This is particularly notable because Trump himself ordered the killing of Soleimani in January 2020. Trump has made several bold claims recently, including an insider secret about JFK Jr.’s political ambitions that he says would have reshaped history.

During the Q&A, Trump also told the audience they could ask about anything, saying, “You can talk sex” and “whatever the hell you want,” signaling a completely open discussion. It was an unusual invitation from a sitting head of state.

On the topic of leadership, Trump concluded, “People that win, it’s much easier to lead when you’re successful, and you win.” He brought up legendary NFL coach Vince Lombardi as an example, calling him “very tough” and “sort of a violent guy.”

Trump noted, however, that Lombardi’s winning record was what ultimately mattered, saying “he won, and he got away with things because he won.” In Trump’s view, success and winning appear to override most other concerns about a leader’s behavior or personality. 

His administration has also been aggressive on other fronts, with Trump’s deportation costs straining city budgets across the country even as Congress approved record funding to expand those operations. The full event in Miami produced a long list of notable moments and comments, with Trump speaking openly on topics ranging from leadership philosophy to geopolitics without much reservation.