Free Thinking Through the Fourth Turning with Sasha Stone
Free Thinking Through the Fourth Turning with Sasha Stone
What Really Happened to Matt Drudge?

What Really Happened to Matt Drudge?

Chris Moody's odyssey to track down the elusive media star makes for a great binge.

In the new podcast series, Finding Matt Drudge, Chris Moody wants to know two things: why Matt Drudge dropped out of sight and why he turned on Donald Trump.

If it is still really Drudge running the DrudgeReport now, and not some paid lackey to push links, then it would not be unreasonable to think he’s hanging on for one last job, to do what Joe Biden, the Lincoln Project, Liz and Dick Cheney, Mike Pence and every other Never Trumper has been trying to do for the last eight years: stop Trump for good.

I got online right around the same time Drudge did. For early internet pioneers, Drudge was our hero who forged a path to success by removing the middleman. Just start a website, and people will come. I was living in a guest house in Van Nuys, California, with a baby on my hip, a 1200 baud modem, and a really good idea.

I launched my site, in 1999, two years after the DrudgeReport launched. The Academy sued me in 2006, and I had to change it to But that was a sign I’d found success, five years after I started. For Drudge it happened instantly and almost overnight. He broke the story of the century: Bill Clinton was having a sexual affair with his intern, Monica Lewinsky.

We all wanted to be Drudge. His success told us we could follow in his footsteps and maybe get that big overnight. It didn’t quite work out that way for most of us. There was only ever going to be one Matt Drudge. But everyone who came after him bit off a little piece of the Drudge legacy.

We would crash the party and upstage traditional media, which was still scrambling to keep up with the fast-moving internet. Drudge was suddenly a reliable source for news. People like me pretended to be journalists, but because we had websites that reported the news, we became reliable sources, too.

And yes, we all wanted a link from Drudge’s site. My memory confuses me sometimes and I think I actually did get linked from him once in the past 25 years, but if that had happened, it would have shut down my site. I would have remembered that.

The closest thing I get to a Matt Drudge story is my good friend Jeff Wells of Jeff was friends with Matt back in the 90s and even went to see Titanic with him in 1997. Drudge linked to Jeff’s site forever until September 2019, when it mysteriously disappeared.

I listened to Finding Matt Drudge slightly differently than most people would. Matt and I are the same species. We’re both creatures of the internet who escaped real life for a life online. That means I understand his need to escape it all probably better than most.

But the podcast itself makes for a compelling listen. Drudge is an enigma, to be sure, and a person I hadn’t thought much about for many years now. As a former Democrat, I didn’t even know he’d been partly responsible for Trump’s rise and that he mysteriously turned on Trump heading into 2020.

After listening to Chris Moody on Megyn Kelly’s show, I started checking the Drudge Report again. It’s still a site full of sexy links, even if most of us now use Twitter in the way we used to use the Drudge Report. I am bothered by the anti-Trump slant because that’s all we see almost everywhere else online.

Like today’s headline:

Trump’s comments related directly to the auto industry, but that didn’t stop many online from running with the casual association to political violence. Why would Drudge link out to that obvious clickbait lie? He must either hate Donald Trump that much (note the sudden absence of the black and white images talked about in the podcast) or his “one last job” is to finish the Trump presidency he maybe feels partly responsible for.

I still have yet to see any violence from the Right, even January 6th, that came close to what Trump supporters have endured:

A headline I would have liked better:


A podcast about Matt Drudge probably wouldn’t be all that interesting if Drudge hadn’t disappeared from the map. Where did he go? Why did he disappear? Did he lose his mind like Howard Hughes or the Unabomber? Or is it something far more mundane, like he just got bored with it all, so he stopped turning up?

His entire career has been shaped by politics, starting with almost bringing down Bill Clinton, then turning his sights to working against Barack Obama, with his friendship with Tracy Sefl - a young Hillary staffer doing oppo research. Hers is one of the best interviews on the podcast:

After Obama’s reign, Drudge turned to Trump as the most exciting thing in politics. He saw what almost no one else could see — a rising star.

Right around this time, in 2015 or so, Drudge interviewed Alex Jones. This was one of his last interviews, and the media devoured it, accusing Drudge of trafficking in “conspiracy theories.” I didn’t see it that way. To me, Drudge seems like a guy who, once again, could see things other people could not.

The interview is not easy to track down, but someone did put it on Youtube once:

Drudge’s reaction to Trump seems personal, unlike “he didn’t build the wall like he said he would.” In the podcast, Moody suggests that maybe the Trump White House slighted him in some way, dissed him, or disregarded him. Or, they suggest, maybe once he got up close and personal with Trump, he didn’t like what he saw.

The story reminds me of a great film called The Year of Living Dangerously, in which a character named Billy (played by Linda Hunt) sees himself as a god-like figure orchestrating Mel Gibson's behavior in the film. Gibson gets a lead for a breaking story, and he’s told to keep quiet about it, or else it will threaten the life of Sigourney Weaver. Gibson, being a journalist, breaks it anyway, and Billy feels betrayed.

Of course, Drudge is not Linda Hunt, and Trump is not Mel Gibson, but you get the general idea. Be careful of people you make into gods - they might only be human.

It’s also possible that Drudge didn’t want to continue as a sycophant for Trump and feels more comfortable in the role of contrarian or provocateur. It’s hard to know why since he won’t talk about it.

The most interesting episode, at least to me, involved Bob Norman, the author of a Columbia Journalism Review piece on Drudge that tries to solve his reasoning behind turning on Trump.

It’s interesting because it gives us an image in our head - a place where Drudge lived and how he reacted when a journalist knocked on his door.

I can tell you this: We internet people don’t like having our personal spaces invaded. We have escaped real life largely because of that, so I understood Drudge’s reaction probably more than most people would.

And that house mentioned in the podcast is easily found online.

And here is the CJR story:

The podcast suggests that Drudge may have outsourced control of his site, but it also suggests that he never would and that once he is no longer interested in doing it, he will disappear, along with the site. Moody talks to people who knew Drudge, like Tucker Carlson and Steve Bannon.

Moody isn’t the only person chasing Matt Drudge, though it is the most entertaining. There are several stories out there, which I will list here, Drudge style:

Shock book: Drudge vs. the algorithms
Investigating the mysterious man behind the Drudge Report
The mystery and intrigue of Matt Drudge's Twitter feed
Drudge, Alex Jones 'Played Crucial Roles' Electing Trump
Matt Drudge Gives A Rare And Really, Really Weird Interview To A Conspiracy Theorist
Who Is Matt Drudge
Drudge Report, a Trump Ally in 2016, Isn't in 2020
What happened to the Drudge Report?

Even if he does take his site offline, the Wayback Machine has it preserved in amber in perpetuity. There, I found this beauty:

By the way, if anyone is interested, you can also find all of Drudge’s now-deleted tweets on the Wayback Machine.

Most people don’t understand us internet types—we see our jobs as playing characters in a way. We have to do so because we have to have a compelling voice. I was the “Oscarwatch” person for many years before anyone knew I was even a female.

The character I play on this Substack, for instance, is the disaffected Liberal who trashes the Left and defends Trump and MAGA. I play that role because it’s interesting to me, but is it everything I am as a person? No. It’s one part of it.

Drudge is the same way. He plays the Drudge guy when he puts on his hat and scrolls the news for links (if he’s even doing it himself). But he obviously has many different facets of his life. He goes to Sweden, Israel, and Vegas—he doesn’t do all that as the Drudge Report guy, I can assure you.

One of the more interesting things you can find on YouTube is a short film of Drudge’s headlines in 2014. Why that year? I have no clue. Even weirder, the video only has around 200 views in total. That might be the best answer to why Drudge disappeared. Maybe he thinks his time has come and gone.

Pinning him down might be harder than one might imagine. It could also be a case of “never meet your heroes.” Maybe people are expecting the Drudge Report guy and maybe he isn’t that guy anymore. Maybe he’s outgrown it.

But I also think now would be a great time for Drudge to return and do what Tucker Carlson is doing on X - speak to the world with a monologue. He’s too bright and observant to just disappear.

Then again, if all he would do was try to put Biden in power for four more years, then no thanks.

Escaping Virtual Life

I listened to Finding Matt Drudge slightly differently than I might have if I hadn’t more or less lived my life the same way he did, as someone who escaped real life and migrated online, then lived there for the next several decades, for better or worse. I tried to have a real life, too, by raising my daughter, dating, and traveling.

It’s harder to build a life offline when you build your whole life online. I have tried to do both, but they are not easy. You have to give yourself over to one or the other to be really good at either.

But a part of me felt sad for Matt Drudge because I know what an isolating, lonely life it can be to interface with the world through a screen. I know he knows that too and I suspect that, more than anything, is motivating him now to switch it off.

Maybe one day, Drudge will disappear as mysteriously as he appeared. And perhaps he will lead an exodus of us internet creatures finding our way back to real life.

Something he couldn’t get or something he lost…

Finding Matt Drudge follows the narrative line of Orson Wells’ Citizen Kane, which starts with one question—what was Rosebud?

If the journalist in that film could answer that question, it might unlock the key to who Kane really was. He doesn’t find out what Rosebud was, but we do. Rosebud was the name of the sled from Kane’s childhood, the last time he felt happy before his life was destroyed by power and wealth.

What might be Drudge’s Rosebud? A matinee in Hollywood in the middle of the day? An old computer? A life without the internet? We’ll never know, and he doesn’t want us to know. We can only guess. The breadcrumbs left in Finding Matt Drudge suggest it’s something as uncomplicated as a good drink and a slot machine in Las Vegas.

You can find the whole podcast on or wherever you get your podcasts.

Free Thinking Through the Fourth Turning with Sasha Stone
Free Thinking Through the Fourth Turning with Sasha Stone
Essays on politics and culture from Sasha Stone's Substack. A former Democrat and Leftist who escaped the bubble to get to know the other side of the country and to take a more critical look at the left.