Trump’s fear of smart people explains absolutely everything: biographer

U.S. President Donald Trump reacts on the day of delivering remarks at Rockland Community College in Suffern, New York, U.S., May 22, 2026. REUTERS Kylie Cooper

In his 1513 political treatise "The Prince," Italian philosopher and statesman Niccolò Machiavelli wrote that truly great leaders surround themselves with the best and brightest advisers they can find. Indeed, he famously summed up his perspective by saying that “the first method for estimating the intelligence of a ruler is to look at the men he has around him.” More than four centuries later, a Republican president named Dwight Eisenhower was rumored to have privately made a similar observation, reportedly saying that "the greatest leaders are the ones smart enough to have people smarter than them around them."

By contrast, according to a journalist with multiple inside sources into President Donald Trump's White House, America's current chief executive has the different philosophy — he surrounds himself with incompetence.

"Speaking on the Inside Trump’s Head podcast, Trump biographer Michael Wolff said, 'This is not a secret,'" reported The Daily Beast's Erkki Forster on Thursday, describing a conversation between Wolff and co-host Joanna Coles. Wolff pointed to Trump's Secretary of Defense, telling Coles that “Pete Hegseth is a... blithering incompetent... yes-man, a suck-up, a man who... knows nothing, and no logic would say he would know enough to run the military-industrial complex."

He added that Hegseth's "primary qualification is that he was... a weekend television co-host. So what in the name of God would he know about running... the United States military... at a moment... in which we are in the middle of a, basically, a revolution in terms of munitions, logistics, and supply.”

Wolff concluded, “Pete Hegseth is in this job because Donald Trump is intimidated by competence. It’s not just that he doesn’t want to be bossed around by people; it’s that he can’t deal with people who know things because—for the obvious reason—because he doesn’t know things.”

This is not the first time Wolff has observed that Trump seems to actively avoid smart people. In August he observed that “he’s filled the administration of the second term with unqualified people, morons of one variety or another, because he can’t have people who are clearly smarter than he is.”

Similarly-famed entrepreneur and investor Jason Calacanis said earlier in September that Presidential Rule No. 1 should be "don't start a never-ending war in the Middle East. Americans have PTSD from them. Presidential Rule No. 2: it's the economy, always has been. Leadership Rule No. 1: Surround yourself with competent people who tell you uncomfortable truths – not sycophants or loyal incompetents. The sycophants will do you in every time. Never get high on your own supply.”

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