SILO RED, SILO BLUE: Kayleigh converted, and so did Greg!

FRIDAY, OCTOBER 17, 2025

They're now part of Numbskull Chic: There they sat, enjoying themselves! Two Fridays ago, on The Five, they engaged in some Numbskull Chic.

They were engaged in American Numbskull Chic—in the familiar gong-show stylings of Fox News Numbskull Chic. 

She had emerged from Harvard Law School; he rates as the channel's top numbskull. Despite their differences, there they sat, citing disputed claims about health care—and on this nation's most-watched "cable news" show, they behaved like a pair of clowns.

It started out like this:

GUTFELD (10/3/25): This is a process that was gamed by illegals, OK? First of all, I looked back and I found out— 

Do you know what has more views that [the Democratic Party's health care] livestream? Rosie O'Donnell's colonoscopy!

PANELISTS: [Laughter]

WATTERS: No!

GUTFELD: And it wasn't—it wasn't even recorded!

WATTERS: Ha ha ha!

GUTFELD: That was four hundred real person views [of the Democratic livestream].

For background, see last Friday's report.

That is typical fare on this dimwitted, garbage can forum. Moments later, up jumped the Harvard Law School grad:

MCENANY: I can't stop thinking about Rosie's colonoscopy. I'm trying to get that image out of my mind.

GUTFELD: Here, you want to see some stuff on my phone? 

[Leans over, shows phone to McEnany]

Looks like the Holland Tunnel. 

MCENANY [Delighted laughter]: Greg downloaded it!

There were no images on the phone. That was just an enjoyable insult aimed at the fading hope of maintaining a viable American nation.

No modern nation can hope to survive these purveyors of Imbecile Chic. Nor can some such nation survive the refusal of elites inside Silo Blue  to report and discuss this daily and nightly behavior.

Kayleigh McEnany, 37 years old, had long been a high achiever. She has no lack of requisite smarts.

We'd be willing to say that she's smart as a whip. We've shown you the basics before:

Kayleigh McEnany 

Kayleigh Michelle McEnany (born April 18, 1988) is an American political commentator, media personality, and former political spokesperson who served as the 33rd White House press secretary during the first Trump administration from 2020 to 2021.

Early in the 2016 Republican Party presidential primaries, she was a critic of Donald Trump but over time became one of his staunchest defenders. 

[...]

McEnany attended the Academy of the Holy Names, a private Catholic preparatory school in Tampa. After graduating, she majored in international politics at Georgetown University's School of Foreign Service in Washington, D.C., and she studied abroad at St Edmund Hall, Oxford...

McEnany attended the University of Miami School of Law for her first (1L) year before transferring to Harvard Law School. At the Miami School of Law, McEnany received the Bruce J. Winick Award for Excellence, a scholarship awarded to students in the top 1% of their class. She graduated from Harvard in 2016.

After studying at Oxford and graduating from Georgetown, she crushed it at Miami Law School, then moved on to Harvard. 

Today, she's one of President Trump's "staunchest defenders"—but that's not the way it started. According to that same leading authority, she experienced a conversion at one point, as quite a few others have done:

While in law school, McEnany appeared on CNN as a paid commentator. She supported Donald Trump in the 2016 presidential election. In early 2015, before becoming a Trump supporter, McEnany was highly critical of him, declaring on CNN and Fox Business that "Donald Trump has shown himself to be a showman" and it was "unfortunate" and "inauthentic" to call him a Republican. McEnany called his comments about Mexican immigrants "racist." 

According to Michael Marcantonio, a fellow summer [2015] associate at a law firm, she began supporting Trump after accepting Marcantonio's advice, which he gave to her over cocktails. In an interview with the New York Times, Marcantonio recalled telling McEnany, "Donald Trump is going to be your nominee," and that if "a smart, young, blond Harvard graduate" wanted "to get on television and have a career as a political pundit, you would be wise to be an early backer."

On August 5, 2017, McEnany left her position at CNN. The following day, she hosted a 90-second webcast, Real News Update on Trump's personal Facebook page. She praised Trump throughout the segment, saying she had brought the "real news" to the American people.

And so on from there. 

We can't vouch for the perfect accuracy of everything said in that brief history. But if you click some links within that overview and read about her initial views, it sounds like McEnany was close to being "woke-adjacent" back when she was anti-Trump.

Today, she's MAGA all the way down, which is her perfect right—and she has her own weekend show on the Fox News Channel. The conversion may have been completely sincere—but there she was on October 3, the Harvard Law School grad, pretending to peer up a good person's colon for the amusement of Silo Red.

What a freaking embarrassment! But then, according to the New York Times, the Trump-worshipping Young Master Gutfeld is a convert too—and it sounds like the CEO may have decided to clue him.

The profile appeared in June 2023:

How Fox News (Yes, Fox News) Managed to Beat ‘The Tonight Show’

[...]

[During calendar year 2015], he also often did something that feels disorienting to rewatch, given the host’s present disdain for those who moralize about Mr. Trump: He moralized about Mr. Trump.

“I’ve heard people defend him about making fun of a disability, making fun of John McCain, making fun of women,” he said on “The Five” in December 2015, accusing a Fox colleague of “Trumpsplaining” away his behavior. “No one will ever stop defending the crass stuff he says.”

Say what? Was this numbskull woke back then too? Candidate Trump was making fun of women—and he didn't even seem to like that!

We'll guess that he, like McEnany, was still voicing support for some degree of the standard Republicanism of the era before Candidate Trump changed the party's public profile.

That would only be a guess. But as he complained about how crass Trump was, this is what happened next:

Before the election, Suzanne Scott, now the chief executive of Fox News Media, hosted Mr. Gutfeld in her office.

Mr. Trump had no chance anyway, he told her.

“She was like, ‘Greg, you should maybe prepare,’” he remembered, “‘for what happens if he wins.’”

So it said in the New York Times in that June 2023 profile. We can't vouch for the perfect accuracy of that anecdote—but it sounds like the CEO called him into her office and suggested that he might want to reorder his stance.

In fairness, CEO Suzanne Scott was running a business. He was one of her corporate assets, and she may have delivered the word. We'll note that the story is sourced to Gutfeld. According to Flegenheimer and Peters, he told that story himself.

Today, this pair of clowns are the type of performers who like to laugh and giggle and play and pretend that they're peering up colons. This is classic Numbskull Chic—as is the silence of the Silo Blue lambs with respect to this ongoing Silo Red conduct.

We'll leave you today with one more point—a point which is skated past in that June 2023 profile.

We'll try to get back to a somewhat unlikely "Fox News feminist" before our discussions are through. But for today, let's return to the large role played by "comedy stylings" in the invention of Numbskull Chic.

That New York Times profile mentioned a book—a seemingly significant 2022 book which largely passed beneath the radar:

Mr. Gutfeld broadly validates the median Fox viewer on the issues that resonate most, including the fate of Mr. Trump, whom Mr. Gutfeld criticized sharply in 2016 before a well-timed recalibration.

He has accused others in late night of failing to adjust as he has and submitting instead to what he sees as an epidemic of left-wing humorlessness.

“It was like Trump was such an existential evil that even joking about it is unseemly,” Mr. Gutfeld said, seated inside his ample Soho apartment (previously occupied by Lindsay Lohan) with a vape pen between his fingers and a large painting of himself in plain view. “I was very anti-Trump up until when he won, and then I had to realize, ‘OK, do I continue as a broken person?’ Because he legitimately was breaking people. Because once the thing that you hate wins, what do you do?”

What Mr. Gutfeld did, in part, was capitalize on a defining talent that he and the former president share: a kind of insult conservatism that can frame any serious argument as a joke and any joke as a serious argument, leaving viewers to suss out the distinction.

“There’s sort of a nihilism at the core of that,” said Nick Marx, a Colorado State University professor and co-author of “That’s Not Funny,” a book about right-leaning comedy. He suggested that Mr. Gutfeld’s shtick was the troubling culmination of Fox’s commingling of news and entertainment.

The book in question emerged in June 2022. Here is a fuller profile:

That's Not Funny: How the Right Makes Comedy Work for Them
By Matt Sienkiewicz and Nick Marx 
May 3, 202
University of California Press

We don't think we heard of the book in real time. To the best of our recollection, we first stumbled upon it quite recently.

That said, it seems that conservative elements had been experimenting with humor as a messaging device, possibly stretching all the way back to Rush Limbaugh and his "feminazis."

For whatever reason, the Fox News Channel experimented with Gutfeld for years, dating back to his original shows at 2 [sic] and 3 [sic] in the morning. Today, CEO Scott sends in coffles of clowns one after another—and a Harvard Law school graduate is willing to behave in the way we've described on our floundering nation's most-watched "cable news" TV program.

Silo Blue gazes off into space. Writing about a different era, Professor Knox, in 1990, described the lesson all Greeks drew from the death of sacred Troy:

The images of that night assault—the blazing palaces, the blood running in the streets, old Priam butchered at the altar, Cassandra raped in the temple, Hector's baby son thrown from the battlements, his wife Andromache dragged off to slavery—all this, foreshadowed in the Iliad, will be stamped indelibly on the consciousness of the Greeks throughout their history, immortalized in lyric poetry, in tragedy, on temple pediments and painted vases, to reinforce the stern lesson of Homer's presentation of the war: that no civilization, no matter how rich, no matter how refined, can long survive once it loses the power to meet force with equal or superior force.

That's the stern lesson the death of Troy taught. Also:

No civilization, no matter how self-impressed, can really expect to survive the fury of the Fox News Channel's Dumbbell Clowncar Chic. 

In short, Silo Blue needs to fight back—and it needs to fight back the right way.

Final point:

The two conversions we've discussed may even have been sincere. But the embarrassing conduct called Numbskull Chic represents an assault on this flailing nation's hope to survive.

There's no excuse for what these people do. Will Silo Blue ever dare speak?

Probably tomorrow: Interruption of Jessica Chic