The fascinating evolution of Matt Drudge

Witnessing the evolution of conservative media mogul Matt Drudge on Donald Trump has been fascinating. Weird, but fascinating.

In case this is your first day on the internet, Matt Drudge is conservative news. Period. He influences what conservative media — and even some media that’s not so conservative, if they’re willing to admit it — write because they covet the eyeballs that his website, The Drudge Report, sends their way if he chooses to link to them.

A little-known journalism figure who exploded to popularity in the late 1990s by breaking the Monica Lewinsky scandal, Drudge became something of a god in conservative circles for helping to topple the legacy of then-President Bill Clinton. And he has remained there ever since. The 53-year-old is worth somewhere north of $150 million, a fortune that he built with a website that was outdated in the late ’90s and hasn’t been updated since. It could be argued that The Drudge Report was a precursor to blogging … but he was certainly the original human aggregator. He rarely breaks stories or writes original content, and even less so in recent years. Rather, he wields influence in conservative politics simply through the stories he links to. His political views are difficult to pigeonhole — he has a libertarian, populist tint that makes him quite a bit like Trump, and he also tends to hinge towards conspiracy theories and far-flung beliefs such as the dangers of artificial intelligence taking over the earth, while also harboring a flair for the dramatic.

There isn’t a conservative media figure anywhere — any media figure, for that matter — who wouldn’t love to command the eyeballs that Drudge commands … somewhere around 10 billion — yes, billion with a “B” — pageviews each year. It’s quite a paradox. He doesn’t write stories, he doesn’t break news … but so many people turn to him to tell them what they should be reading that he is a millionaire many times over simply by linking stories, and he commands the respect of the Republican establishment as a result.

Early during the 2016 presidential primary season, Drudge got on the Trump train. It could easily be argued that Drudge is the single biggest reason why Trump won the presidency — though Trump would never admit it.

That’s what makes Drudge’s evolution from 2016 to 2020 so oddly fascinating. Because now, quite obviously, Matt Drudge detests Trump and would love to see him out of the White House — apparently at any cost. There has never been an ounce of love lost between Drudge and the Democrats, but one senses from reading the damaging headlines that Drudge serves up on Trump that he wouldn’t mind seeing a Democrat in the Oval Office if it meant Trump’s demise.

The mainstream media began to catch on that something was wrong last fall, when Drudge began dishing up unflattering headlines on the president during the impeachment saga. In late November, the Daily Beast pondered, “What’s going on with Drudge?” I had been asking the same question at least that far back. What in the world was going on, indeed? Trump and Drudge were quite the marriage during the 2016 election cycle. When Trump would brand one of his political opponents, Drudge would employ Trump’s nicknames for his adversaries. When Trump began attacking Ted Cruz — his biggest challenger during the primary season — Drudge began attacking Cruz. I blogged at the time that Drudge was using The Drudge Report as an arm of the Trump campaign. Drudge made Trump a viable candidate, and he also shoved the GatewayPundit blog into the mainstream by constantly linking their content.

And the marriage didn’t end with Trump’s election. Drudge was a frequent early visitor to the White House after Trump took office.

But at some point, and for some reason, the honeymoon ended. Apparently, the split wasn’t amicable.

If reports are to be believed, Trump had no idea it was coming. In November, he directed his advisor and son-in-law, Jared Kushner, to investigate. There was no word on what Kushner uncovered.

Freelancer Bob Norman took it upon himself to drive to Drudge’s South Florida estate in an effort to corner the reclusive Drudge. Like everyone else, Norman didn’t get much out of Drudge.

After going back and forth for several more minutes, he finally asked me what I wanted to talk about. I told him I was curious about his current thoughts on Trump.

“You and everybody else,” he said.

I noted that he went all in on Trump during the election.

“That was three years ago,” he said.

There has been plenty of speculation that Drudge has soured on Trump over the border wall — or lack thereof. But anyone’s guess is apparently as good as anyone else’s.

Whatever the reason, Trump hasn’t gone after Drudge the way he goes after most of his rivals — which says something about the respect that Drudge commands. But things have become even more strained during the coronavirus pandemic. Drudge’s choice of headlines have made it clear that he’s pulling no punches … so why, then, would Trump keep quiet in an effort to avoid invoking Drudge’s ire?

Finally, late last month, Trump could contain himself no longer. He took a shot at Drudge through his favorite medium — Twitter — and Drudge, in a rare move, fired back. Sorta.

It’s worth noting that Drudge isn’t the only conservative media figure who has soured on Trump. Far from it. Ann Coulter was once one of Trump’s staunchest allies in the media. She even wrote a book entitled, In Trump We Trust. But she abandoned him over immigration issues — which was perhaps the same straw that broke Drudge’s back — and the two became bitter enemies last year, tweeting insults at one another. (Trump called Coulter a “wacky nut job”; she called him “lazy and incompetent.”)

Even Michael Savage, while still supportive of Trump, has at times voiced his doubts. Savage once bragged that he and Drudge had done more than anyone else to get Trump elected.

But the evolution of Matt Drudge is certainly the most interesting of the three. He probably isn’t too worried about potential fallout from a feud with Trump … he started his working life as a convenience store night clerk, and he’s since made enough money to live more than comfortably. Given his reclusive nature, he probably isn’t overly concerned about fame.

Still, it was conservatives and their voracious hunger for the written (and spoken) word that made Matt Drudge … and that same conservative base may have remained loyal to him through the years, but they’re also loyal to Trump — and it seems likely that Trump can do far more to damage Drudge than Drudge can do to damage Trump (which is what makes Trump’s relative silence on Drudge somewhat interesting). In his efforts to bring Trump down, the familiarly unapologetic conservative tone of The Drudge Report has changed considerably, which makes it a wonder that he’s still maintaining the number of eyeballs that he is. At one point, before I began to understand that Drudge now has an open disdain for Trump, I wondered out loud if Drudge might have quietly sold out to a liberal curator. So deep is his dislike for Trump that he’s apparently willing to stake the very legacy of his empire on his campaign against the president.

If Drudge did, in fact, elect Trump, can he also un-elect him? Given his actions thus far, it seems that he’s going to do everything in his power to try. But it also seems like he’s created a monster he will not be able to put back in its cage.

Ben Garrett

Ben Garrett is a journalist from East Tennessee. He is publisher of the Independent Herald, a weekly newspaper serving the Big South Fork region of the Cumberland Plateau, with a sideline in website development and digital marketing. He is also an erstwhile blogger.

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