How Greg Gutfeld Went From Fox’s Most Irreverent Host to Its Most Servile

Evan Agostini/Invision/AP

Fox News host Greg Gutfeld is on top of the world right now, at least professionally. He co-hosts The Five, his network’s top-rated show that pulls in more than four million viewers every weeknight. Roughly three million people watch his late-evening show, Gutfeld!, earning him the moniker of “The King of Late Night” (which is also the title of his bestselling book). Earlier this month, his guest appearance on The Tonight Show Starring Jimmy Fallon, drew the program’s biggest ratings of the year.

Indeed, Gutfeld’s come a long way since his hosting duties on Red Eye, Fox’s satirical, take-no-prisoners 3 a.m. program that debuted in 2007. The show was extraordinary departure from other Fox programming at the time. When viewers tuned in, they entered a bizarre world of sharp-witted political tomfoolery, lengthy animal videos, talking makeshift props, masochistic treatment of “repulsive” sidekicks, and jaw-dropping tales of house boys locked in basements.

It was must-see-TV, and featured a variety of fresh-faced guests from across the cultural spectrum, including pundits, political figures, comedians, musicians, and strait-laced journalists who seemed to relish the opportunity to finally let their hair down.

What perhaps stood above all else was the political irreverence of Gutfeld and his on-air accomplices, Bill Schulz and Andy Levy. They didn’t just tamp down partisan hackery and conspiratorial nonsense, but openly (and quite cleverly) mocked it.

Of course, nothing lasts forever. Gutfeld left Red Eye in early 2015 to focus on bigger things at the network: The Five and a new weekend show of his own, where he showcased his wit and mix of conservative and libertarian views to a much broader (and more awake) audience.

His future was bright. But as well know, Donald Trump’s entrance into politics a few months later turned the conservative media on its head. The celebrity businessman’s hostile takeover of the Republican Party pitted many commentators against a rapidly changing, increasingly populist base. Conservative pundits who “adapted” to the situation by surrendered their long-preached principles and standards of conduct managed to hold onto (and even their grow) their audience. The dwindling number of those who held strong watched their viewership, listenership, and readership evaporate before their eyes.

To Gutfeld’s credit, he stuck to his guns longer than most. Throughout the election, he debunked Trump’s lies, openly called out the hypocrisy of his Fox colleagues (many of whom brazenly served as Trump cheerleaders), and critiqued the absurd amount of airtime Fox was devoting to Trump’s campaign.

“When Trump breaks wind, we cut in,” a frustrated Gutfeld once quipped as Fox broke away from regular programming to live-cover a Trump campaign speech.

A particular Gutfeld monologue in 2015, right after Trump mocked John McCain for his capture, imprisonment, and torture as a prisoner of war, is what many still remember from the Fox host during that time. Gutfeld spoke directly and candidly to the Fox audience about the importance of holding Trump to standards:

Donald’s not to blame for being Donald. The fault lies with those who yield to his rules — that either you’re a groupie or a traitor. But in reality, critics beat both. Groupies offer little insight — just rope and dope. His repeat defenders always paint Trump’s gaffes as blunt honesty, which turns them into Bill Maher’s audience: compliant; they let stuff slide… When you perceive criticism as disloyalty, you turn fans into minions. But criticism is your guardrail.

It’s hard to think of anyone who could use that message more than the Greg Gutfeld of today.

After Trump unexpectedly won the presidency in November of 2016, and it was clear the conservative media’s election-season foray into MAGA fandom would settle into a long-term business model, Gutfeld began a rather fast journey from Fox’s most irreverent on-air personality to arguably its most servile.

By the time Trump was sworn into office, Gutfeld had (as he had once warned against) yielded to the new president’s rules. He largely abandoned his criticism of Trump, and took on the role of loyal fawner and flatterer, turning reflexively hostile toward Trump’s critics (including pretty much anyone on the right who had the gall to speak negatively about him).

It’s steadily gotten worse.

Earlier this month, Gutfeld, in defending Trump, went from merely downplaying the violence of January 6, 2021, to outright denying that Capitol police were meaningfully assaulted that day. This, of course, would come as a surprise to the almost 150 cops that were injured during the riot (some so badly that they had to retire from the force).

And just last week, Gutfeld openly considered that the FBI’s search of John Bolton’s home and office was an act of political retribution… right before justifying it as such.

“Some people say it’s retribution, I say who cares,” he said on The Five. “Don’t lecture me on timing of lawfare. Don’t lecture me on politically motivated investigations. You guys invented this stuff. You loved doing it to Trump… The Dems never expect it to happen to them. They’re like home invaders who didn’t expect a well-armed occupant when they showed up. And Trump is well-armed.”

There were some obvious flaws, even in his “eye for an eye” rationale. Bolton is hardly a Democrat, and he had nothing to do with any of the criminal cases against Donald Trump. Even if one subscribes to the notion that charging a former and possibly future U.S. president with a crime (no matter how compelling the evidence) is inherently “lawfare,” and therefore fair game for reprisal, what exactly is the argument for dragging a third party into the crossfire?

It’s also hard to overlook some personal significance to Gutfeld’s comments. Bolton, as some may remember, was a revered regular guest on Red Eye. In fact, Gutfeld and company felt so highly of him that they dubbed him “The President of Red Eye.” Now, it seems Gutfeld is perfectly comfortable condoning the use of government force to inflict retribution on his old pal… for the crime of being a Trump critic.

So much for “criticism is your guardrail.”

John Bolton with Greg Gutfeld on Fox News show Red Eye.

But Gutfeld wasn’t done. He followed up his comments by advocating for even less constraint from Republicans, while taking a stiff shot at traditional conservatives who still support institutional guardrails.

“This is kind of an ongoing masterclass for the Republican Party — the new Republican Party,” he said. “The conservative movement, which I loved for a longest time… They were kind of happy to fritter away their influence and power on the notion that they were always above returning fire.” In a mocking tone, he added, “’Uh, I write for National Review. This is disgusting! Let’s write a 4,000-word piece on judicial reform.’ Then they don’t do anything. They go back and smoke their cigar.”

It’s unclear what Gutfeld expects political commentators to “do,” exactly, besides offer critiques and present arguments and ideas. Does Gutfeld, a commentator himself, do more than that? Has he been using his “influence and power” for anything beyond marveling at Trump’s greatness, slamming his critics, and taking home a big paycheck? Is smoking weed more productive than smoking cigars?

Gutfeld surely used to think that sound arguments mattered. The old Greg wrote an entire book on the importance of persuading others. It was called, How to Be Right: the Art of Being Persuasively Correct, and included the chapters “Discard Your Outrage” and “Outcompassion Them.” The book’s marketing blurb reads: “To survive, the right must learn how to express nonliberal principles as effectively as possible and persuade others of their point of view.”

Apparently, in practice, that sort of thing is just too much work. It’s way easier (and better for ratings) to point a finger at Democrats and defend your guy’s worst behavior with a hearty, “They did it first!”

With Gutfeld drifting deeper and deeper into “anything goes” territory, it will be interesting to see what he’s saying six months from now. He hasn’t quite reached the level of reckless abandon that Tucker Carlson achieved at Fox before his unceremonious exit, so there’s possibly still room to grow.

What we do know is that there will be an audience for it.

John A. Daly is a political writer, podcaster, and thriller novelist who writes primarily for BernardGoldberg.com.

This is an opinion piece. The views expressed in this article are those of just the author.