The Challenge of Covering Donald Trump in Modern Journalism

Engaging with Donald Trump is, I suppose, a persistent challenge for journalists, for various reasons. His temperament, for one. The speed of his actions. And let’s not overlook the volume he brings—his capability to generate multiple news cycles before most reporters finish their morning coffee is remarkable.

But there’s one aspect that often slips under the radar, and it might just be the most significant of all. Donald Trump seems to possess a deeper understanding of the news business than any recent president, perhaps even more than some of those working within it.

This might come as a surprise—or perhaps it shouldn’t.

Changes in the Media Landscape

CNN, for instance, is expected to see its viewer ratings drop significantly from the boost it received during Trump’s presidency in 2017, as we move toward 2025.

Trump didn’t grow up in a space that was particularly welcoming to his political views. Before diving into political campaigning as a Republican, he was a businessman and reality TV figure known for indulging in juicy, often exaggerated gossip, as demonstrated by a column from New York Post’s Cindy Adams. His playful rapport with the press helped craft his larger-than-life persona.

Once he entered the realm of politics, however, things took a turn. Just like George W. Bush earlier, Trump had to learn how news organizations operate in an adversarial atmosphere. No unconditional support came his way. He faced skepticism and had to navigate the system meticulously to thrive.

He adapted, and quite effectively.

President Trump regards the media as a challenger, an adversary, a tactical platform, and at times, a target. He studies it like an astute student of political science and tests it like a boxer gauging his rival’s defenses.

The Nature of Trump’s Relationship with Media

Previous Democratic presidents, such as Bill Clinton, Barack Obama, and Joe Biden, operated within media environments that were, by and large, sympathetic—even if not wholly favorable. Though they faced criticism, it often came with understanding and context. Their errors typically received some cushion from interpretative leniency.

Trump, however, didn’t have that privilege.

Before he announced his candidacy in 2015, he had been watching the media closely. Observing patterns, he took note of who garnered genuine attention and who was labeled as “dangerous.” He became adept at recognizing which stories gained traction and which were quickly forgotten.

In his analysis, he identified a cultural bias—a perception that sometimes impacted reporting standards. Not every article or journalist might be biased, but there was definitely an overarching atmosphere. Trump perceived assumptions about what was considered normal versus extreme, concluding that many conservatives felt threatened and alienated, which struck a chord with millions.

He also noted elitism: newsrooms predominantly situated in coastal cities cultivated an insular culture. Journalists shared similar backgrounds and circles rather than connecting with the “ordinary Americans” they so often discussed. Many in the media struggled to grasp how issues like illegal immigration impacted communities and why trade agreements felt personally detrimental in manufacturing towns.

Thirdly, he recognized a failing business model. Traditional media outlets had faltered during the digital transformation, leading to downsizing and financial instability. Some adapted, but many didn’t; layoffs became a regular occurrence, and survival began to look uncertain.

These intertwined problems paved the way for a crisis of trust.

When audiences perceive bias, distance, and despair, their trust erodes. And reestablishing that trust is a gargantuan challenge.

The Paradox of Trump’s Media Strategy

Ironically, as Trump criticized media shortcomings, he didn’t rectify them; he amplified them.

His critiques forced journalists into a defensive posture. They tightened their ranks and became increasingly ideological and closed-minded. With each attack, their conviction about doing the right thing only grew stronger, even if the result was the opposite.

Trump transformed his disputes with the press into a persistent political weapon. While previous Republican leaders might grumble about media coverage, he turned that frustration into a spectacle. He fundamentally altered the dynamic, conceiving not just the stories themselves but making the press a character in his narrative—a villain operating in the shadows.

With humor, exaggeration, and showmanship, he effectively utilized the media.

This wasn’t by chance.

Understanding Modern Journalism

Behind the scenes, Trump and his team learned what drives today’s journalism. They figured out which outlets chase clicks, which reporters thrive in controversy, and the phrases that attract attention. They understood the mechanisms of news circulation and how to manipulate them.

Anger fuels engagement. Conflict serves as currency. Attention equates to influence.

Importantly, their supporters take delight in watching this all unfold. Criticism is often viewed as a sign of persecution, while coverage validates their significance. Attacks on Trump serve as motivation.

In politics, knowledge equates to power, and Trump’s savvy approach to media has granted him considerable leverage over them and his political base.

He plays within the framework as it exists, not as journalists envision it.

He sees the media not just as a political opponent but as a competitor, vying for the same audience and attention.

Trump approaches the press as a rival—a platform, and yes, a punching bag. He meticulously studies it, probing for weaknesses.

In a world where trust is scarce and attention spans are fleeting, his understanding of these dynamics might just be his greatest political asset.

Donald Trump exhibits a grasp of the news business’s inner workings that is arguably unmatched, leveraging this insight to his advantage.