There are many reasons why covering Donald Trump is the journalistic challenge of a lifetime.
His temperament. His speed. Its volume. The mere fact that he can generate three news cycles before most reporters have had their first cup of coffee.
But there’s one often overlooked explanation that may be the most important of all: Donald Trump understands the news business better than any modern president — in many cases better than the people who work in it.
That may sound surprising. That shouldn’t be the case.
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Trump did not grow up in a politically friendly area. Things were different for him before he entered the campaign world as a Republican. As a businessman and then reality TV star, Trump enjoyed tasteless and generally glorifying gossip, including in the August columns of New York Post legend Cindy Adams. His friendly, bantering relations with the press helped transform him into a larger-than-life figure.
But that all changed when he entered the political fray. Like George W. Bush before him, Trump learned how the press really works in a hostile environment. He never automatically received goodwill. He was rarely given the benefit of the doubt. He had to study the system, test it, provoke it, and sometimes fight it to survive.
So he learned.
And he learned well.
Trump treats the media as a rival, a foil, a platform and a punching bag. He studies it as a brilliant Ph.D. student. He examines it like a boxer testing the defense.
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Other recent presidents – Democrats Bill Clinton, Barack Obama and Joe Biden – operated in a media climate that, while not always friendly, was structurally sympathetic. They were criticized, yes. But they were also understood. Generously interpreted. Given the time. Patience granted. Their mistakes were often mitigated by context and explanation.
Trump never had that luxury.
President Donald Trump knows exactly where the media is exposed and vulnerable. (Andrew Harnick/Getty Images)
Long before he descended the escalator in 2015 – long before demonstrations, red hats and chants – he was paying attention. To look. Noticing patterns. Examining how stories were framed. Which was treated as ‘serious’. Which was treated as ‘dangerous’. Which stories stuck. Some faded. What sins were forgiven. That were never forgotten.
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And he came to some conclusions.
He saw, first and foremost, a cultural bias — not necessarily in every article or reporter, but in the air those newsrooms breathe. In assumptions about what is normal and what is radical. In who is considered reasonable and who is considered reckless. The conservatives, he concluded, were playing uphill — and tens of millions of Americans knew it. It made them angry.
Second, he saw elitism: newsrooms clustered in a handful of coastal cities; journalists with similar educations, similar friends and similar politics. The press talked endlessly about “ordinary Americans,” growing further removed from them every year. It was difficult to understand why illegal immigration worried so many families, or why trade deals in factory towns felt like personal losses.
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Third, he saw a broken business model: newspapers and networks missing the digital revolution; revenues shrink; newsrooms are shrinking; panic struck. A few electrical outlets found lifelines. Most don’t. Layoffs became routine. Survival became uncertain.
And from these three problems arose the fourth: wavering confidence.
When the public sees prejudice, distance and despair, trust erodes. And once credibility is gone, it’s almost impossible to restore it.
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Here’s the great irony:
When Trump started attacking the media for these shortcomings, he didn’t fix them. He intensified them.
His criticism put news organizations on the defensive. They closed ranks. They hardened. They became more ideological, more insular and more fragile. Each attack convinced them that they must be doing something right. Often it meant the opposite.
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Trump, meanwhile, turned his feud with the press into a permanent political weapon.
Before him, Republicans sometimes complained about the reporting. But Trump transformed his displeasure into theater. He didn’t just dispute stories. He turned the media itself into a character in his drama: the villain, always lurking, always making plans.
With humor. With mockery. With exaggeration. With showmanship.
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And it worked.
It still works.
This was never a coincidence.
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Behind the scenes, Trump and his advisers learned the incentives of modern journalism. They know which outlets are hungry for clicks. Which reporters thrive on conflict. Which controversies spread the fastest? Which sentences become headlines. Which misdeeds reach the furthest.
President Donald Trump speaks to reporters before departing the White House in Washington, DC on February 6, 2026. (ANDREW CABALLERO-REYNOLDS/AFP via Getty Images)
They understand the machinery.
They know how to activate it. How to make it flood. How to redirect it. How to exhaust it.
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They know that outrage is oxygen. That conflict is a currency. That attention is power.
And they know their supporters will love watching it all unfold.
Criticism becomes evidence of persecution. The coverage becomes a confirmation of the importance. Attacks become fuel.
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Knowledge is power in politics. And Trump’s knowledge of the media has given him power – over the press and over his own movement.
He plays the system as it exists, and not as journalists wish.
President Donald Trump and first lady Melania Trump arrive for the premiere of “Melania” at the John F. Kennedy Memorial Center For The Performing Arts, Thursday, Jan. 29, 2026, in Washington. (AP Photo/Jose Luis Magana)
He understands that modern news is part information, part entertainment, and part martial arts. He understands that stories are more important than footnotes. That emotion wins over nuance. That speed beats reflection.
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So he moves quickly. He moves loudly. He moves relentlessly.
For reporters and news organizations, this is the real challenge:
Not just about what Trump says and does – but about someone who understands the financial, cultural and psychological vulnerabilities of their sector and is constantly putting pressure on them.
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Every weakness becomes a lever. Every habit becomes a pressure point.
Trump is not only running against and competing with Democrats.
He opposes and competes with the media.
President Donald Trump during an announcement in the South Court Auditorium of the Eisenhower Executive Office Building at the White House in Washington, DC, on Thursday, February 5, 2026. (Aaron Schwartz/CNP/Bloomberg via Getty Images)
He sees it as a rival, a foil, a stage and a punching bag. He studies it as a brilliant Ph.D. student. He examines it like a boxer testing the defense.
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And he knows exactly where it is vulnerable and vulnerable.
At a time when trust is scarce and attention is priceless, that knowledge could be his greatest political asset.
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Better than any president in modern history—perhaps better than almost anyone in public life today—Donald Trump understands how the news business really works.
And he knows how to use that insight to his advantage.
CLICK HERE TO BY MARK HALPERIN
