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Why Matt Drudge’s Feud With Donald Trump Matters

The falling-out says a lot about the state of conservative media in 2020—and may herald some good news for Joe Biden.

Evan Agostini/Getty Images, Jamie Squire/Getty Images

In the summer of 2016, Matt Drudge hammered the same story again and again on his eponymous news aggregation website, the Drudge Report: Hillary Clinton was not well. She was old and sick and feeble, unable to navigate even a small set of steps without the help of multiple aides. These stories, often coupled with the hashtag #HillaryHealth, complemented the narrative that Clinton was, with her husband, a symbol of the decaying, corrupt political establishment.

Drudge had already helped Donald Trump immensely, earlier in the campaign cycle, by focusing his ire on primary rivals like Jeb Bush and Ted Cruz. While many news outlets stressed the role that newer conservative publications, particularly Breitbart, played in Trump’s surprise victory in 2016, none played a more decisive role than the Drudge Report.

Four years later, it is Trump who is being depicted as a deranged, infirm maniac. In just the last week, Drudge has hailed Joe Biden’s attacks against the president and amplified Trump’s bizarre, unprovoked denial that a series of mini-strokes sent him to Walter Reed Hospital last fall.

What happened? Trump’s allies in conservative media think they know. In June, Tucker Carlson described Drudge as “firmly a man of the progressive left” and suggested that the site was now comparable to The Daily Beast or “any other woke propaganda outlet posing as a news company.” Radio host and Fox News regular Mark Levin has described the Drudge Report as a “NeverTrumper” site. On Tuesday, the president himself weighed in, incorrectly claiming, “Drudge didn’t support me in 2016.”

The exact details of the Trump-Drudge divorce remain shrouded in mystery, thanks in large part to Matt Drudge’s status as the Howard Hughes of media. Ensconced in south Florida, he rarely grants interviews and hasn’t commented on the split. (When a Columbia Journalism Review reporter told him that he was curious about his thoughts on his president, Drudge replied, “You and everybody else.”) But a closer look at Drudge and his role as a media impresario reveals clues both to his own behavior and the current state of the conservative infotainment complex.

Drudge’s sensibility has always been more tabloid than ideological. He has broken some huge stories—most famously Bill Clinton’s affair with Monica Lewinsky—but the precise nature of his influence has always been hard to pin down. John Harris and Mark Halperin whiffed when they described him as the “Walter Cronkite of our era.” Brian Williams came closer when, in 2007, he described the Drudge Report as “America’s bulletin board, and much more than that.” Obsessed over by reporters and politicians alike, it has greater influence and a bigger audience than tip sheets like Politico’s Playbook. Drudge’s knack is for turning gossip into news, whether it is trivial but real (John Edwards’s $400 haircut during the 2008 primary) or fake and malicious (a Bill Clinton Black love child, a claim that Barack Obama’s birth certificate was forged).

Much of Drudge’s early success came from filling a void. The early online political press skewed left; Drudge appeared as a correction and, as a result, instantly gained millions of readers who were looking for a different perspective. At the same time, Drudge is idiosyncratic and obsessed with things that rarely feature in the political press: the box office, celebrity gossip, weird sex, and conspiracy theories, particularly involving government surveillance. He is not here, like Fox News, solely to do conservative agitprop. He’s a muckraker and gossip hound fixated on the buttoned-up press’s failures to report all that’s lurid and controversial—i.e., the good stuff. He’s less Walter Cronkite than some unholy cross between Gawker and Milo Yiannopoulos (an old Drudge favorite).

Does Drudge even have a political viewpoint? He loved Hillary Clinton before he hated her. As Philip Weiss wrote in New York in 2007, “The one person Drudge seems to believe can lead is Hillary Clinton. Though Drudge often savages Hillary, he is convinced that she will make history, and he seems determined, in spite of himself, to empower her.” He fixated on Clinton’s rivals that year in much the same way he focused on Trump’s eight years later. “That House is going pink,” Drudge said in 2007.

Drudge claimed in 2017 that he had long admired Trump. “I liked Donald the man even before he ran,” he told radio host Michael Savage. “He is one of the most fascinating Americans that have ever lived in the modern era. He is a throwback. He’s old school.… Charisma. Charisma is needed in this job.”

Trump’s anti-establishment leanings also endeared him to Drudge, who sees himself as a crusader against the decadent, corporate media. As a result, writes Matthew Lysiak in his book about Drudge, “Matt focused the vast powers of his website on methodically taking down everyone that stood in Trump’s path.” When bad polling came in, the Trump campaign’s reaction was to call Drudge. “Fuck the corporate media,” he reportedly told them, adding, “They’ve been wrong on everything. They’ll be wrong on this.”

Although he hated Steve Bannon, he was welcomed into the inner circle by Jared Kushner. In the first two years of Trump’s presidency, Drudge served as one of Kushner’s key allies, fighting proxy wars on his behalf. “Drudge was treated by the campaign and Kushner like he was the pope,” a former campaign official told Lysiak. In a comment laced with homophobia, another said that he suspected Drudge had a “crush” on Kushner.

At first, the break with Trump appeared to be ideological. Like Anne Coulter, Drudge was disappointed that the president had failed to live up to his xenophobic campaign promises to build The Wall. Over the last two years, that rift has grown deeper and more personal. In his interview with Savage in 2017, he said that he wished Trump would focus on leading: “Nixon wasn’t in your face. Since when did the president become someone who was in your face daily?”

Whatever the case might be, Drudge has had his finger on the pulse of a certain political zeitgeist for decades. His falling out with the president, though certainly personal, appears to speak to a widespread disillusionment with Trump, even among people who aren’t revolted by him and had hoped he would shake things up.

Most of the rest of conservative media has made the opposite conclusion. Trump has a devoted audience, and pissing them off comes with serious consequences for the bottom line. Spinning Trump’s failures to his base is a lucrative cottage industry. The more slavishly devoted you are to the president, the more you are rewarded. One’s conservative credentials are now based on following the president’s whims wherever they lead. Drudge, always the self-styled outsider, is thumbing his nose at the establishment once again. This time, however, it’s the conservative media establishment he helped create.