Taking Offense
| May 27, 2025CNN’s Scott Jennings is the personal voice for the unheard masses
Photos: Naftoli Goldgrab
The yellow ribbon pinned to his lapel in every appearance symbolizes not only his solidarity with the Jewish hostages in Gaza — it’s a bold expression of the unapologetic authenticity he believes is the future of politics
Shortly after 10 p.m. on an otherwise unremarkable April night two years ago, the control room doors at CNN’s New York headquarters swung open.
Scott Jennings peered inside and felt his pulse quicken. The political analyst — a Kentucky native whose tailored suits complement his Appalachian twang — spotted an unexpected guest sitting at the panel beneath the klieg lights: Randi Weingarten, president of the American Federation of Teachers.
At the last minute, the producers decided they would keep Weingarten on set after her interview with host Alisyn Camerota. It was a break from standard protocol. Typically, guests exit after their segment. But this time, she would stay — joining the post-interview panel. Jennings, the lone conservative, would be seated just inches from her. The timing could not have been more charged: America’s parents were still seething over the prolonged Covid school closures, and Weingarten had spent the week on Capitol Hill defending her role in them.
“I looked at the stage manager and said, ‘You’re putting her out there with me?’ ” Jennings recalls. “He nodded. I had about 60 seconds to channel every frustrated mom and dad in America.”
He did just that.
The moment wasn’t loud. It wasn’t performative. But it was real, and unmistakably personal.
“We don’t know each other,” Jennings began, looking directly across the table at Weingarten, “but speaking on behalf of millions of American parents, I am stunned at what you have said this week about your claiming to have wanted to reopen schools. I think you’ll find that most parents believe you were the tip of the spear of school closures.”
Jennings’s voice was steady, but the emotion just beneath the surface was unmistakable as he continued.
“There are numerous statements you made over the summer of 2020 scaring people to death about the possibility of opening schools. And I hear no remorse whatsoever about the generational damage that’s been done to these — I have two kids with learning differences. Do you know how hard it is for them to learn at home and not in a classroom that was designed for them?
“And for you to sit in front of Congress and the American people and say, ‘Oh, I wanted to open up the whole time’ — I am shocked. I’m stunned. I’m stunned. And there are millions of parents who feel the exact same way.”
It didn’t take long for the verbal offensive to find a second life. Clips of the exchange ricocheted across social media — spreading through WhatsApp chats, X posts, YouTube recaps, and the endless churn of podcast highlight reels. Fox News ran a segment hailing Jennings as a “MAGA star,” while the Washington Free Beacon summed it up with a headline that simply read: “BEASTMODE: Conservative Dad Torches Randi Weingarten Over School Closures.”
For many parents, it was less about the politics and more about the emotional release — someone, finally, saying what they had felt for years. For CNN, it was a rare breach of script in the overwhelming sea of liberal coverage.
For Scott Jennings, those 60 viral seconds were a breakout moment when he emerged as an unfiltered, unmistakably conservative voice on the national stage.
That moment encapsulated what makes Jennings unique in today’s political media landscape. Over the past few years, he has built a reputation not just as a sharp conservative analyst, but as a voice for viewers who feel unheard — parents, voters, and working Americans who don’t necessarily want bombast, but clarity. In a medium built on noise, he’s managed to stand out by staying steady — speaking plainly, often personally, and always with a sense of what’s at stake beyond the Beltway.
“If I had to take one lesson out of that moment with Randi, it was that I delivered all the raw, authentic emotion that any dad could,” he says. “And it reminded me that there’s a craving for that in our culture right now, for authenticity, and that’s what I’m trying to channel every day.”
Smooth Operator
Up close, it’s easy to see why Scott Jennings thrives on TV. His CNN persona — that affable, all-American adult-in-the-room who calmly, but forcefully, chimes in as the voice of reason only once everyone else at the table is done bickering — is the same one you experience when you sit across from him.
Those interactions are marked by a thoughtful openness, even as he maintains a firm grasp on his message. The smoothness feels steady but natural, not performed — a byproduct of speaking genuinely and without needing to remember what he’s “supposed” to say.
“Let me tell you something about authenticity,” Jennings says, pausing for a moment. “It’s the coin of the realm in politics and media. The politicians and the media people who succeed in the future are going to be the ones who speak their own minds, and not somebody else’s.
“The scripted era is over,” he continues. “That’s why these podcasters and these YouTubers and these new media people are succeeding, because there is an authenticity in what they’re doing. They’re not the most polished. They’re not out here reading scripts. They’re just being themselves. They’re being raw. They’re being authentic.”
Authenticity is the tie that binds Jennings to President Trump as well, and how he understands the president’s ability to connect with people he doesn’t otherwise seem to have any commonality with.
“Trump’s campaign in 2016,” he says, “was kind of the beginning of the war on pablum” — the word Jennings uses to describe bland, generic, or overly sanitized political speech. “All the politicians used to speak the same pablum. He comes along and just talks like you might talk. I think there are millions of people — especially non-political people who hear in his voice phrases and words and statements that they think, ‘Oh, I might have said it that way if someone had asked me.’
“So he’s speaking for them, not just in terms of policy but in terms of language. And you know, I hear all the media people and all the professionals to this day going after Trump for the way he speaks, and I just think, ‘You don’t get it.’ He is speaking to people in the way they imagine they might speak. And there’s an authenticity in it… it’s like connective tissue. People ask me a lot, ‘How does a rich New York real-estate guy get so liked by poor Appalachian coal miners?’ That’s it — the language and the willingness to display it. That’s the connective tissue. And the elites don’t get it. They never will.”
In a media landscape where such authenticity is increasingly scarce, Jennings’s remarkably novel approach resonates deeply with viewers who have felt starved of it. Study after study has shown that with every passing year, Americans’ trust in the legacy media, broadly defined as the media institutions that have been around for years, keeps declining to alarming levels.
The most recent example of this is the Gallup poll, which has measured this for over half a century. Their latest poll found that 69 percent of Americans say they have either not very much or no confidence at all in mass media to report news fully, accurately, and fairly. Trust has fallen so low that it trails even the three branches of the federal government, institutions not exactly enjoying a golden era of credibility.
But perhaps most importantly to what Jennings almost stumbled across, the primary driver of this distrust is the 59 percent of Republicans and 42 percent of independents who say they have no trust in newspapers and television at all.
And yet, among the media “elites,” there remains a sort of performative indignation rather than introspection.
Just this past November, Axios CEO Jim VandeHei accepted an award at the National Press Club — using the post-election moment not to reflect on the trust gap, but to lash out at Elon Musk.
Responding to Musk’s post on X that “You are the media now,” VandeHei thundered, “That’s nonsense! Being a reporter is hard — really hard. You have to care. You have to do the hard work… You don’t do that by popping off on Twitter [and] by having an opinion!”
But as Jennings — and millions of regular Americans see it, that is completely missing the point. The problem isn’t that reporters don’t work enough — it’s that they don’t listen enough.
As Batya Ungar-Sargon writes in her 2021 book Bad News: How Woke Media Is Undermining Democracy, “There’s a simple reason why Americans feel so alienated from the media and journalists who are supposed to be writing the first draft of American history: The reason is because they are alienated from them.”
Ungar-Sargon methodically details how media itself underwent what she calls a “status revolution,” where it transformed from an undertaking on the part of the working class to one dominated by the upper class and “elites.” What was once the pursuit of the “regular person” and a way for them to hold the powerful to account, essentially became a pursuit for the rich and upper-class, and a way for them to create a medium in which they controlled what “reality” is.
But selling that sort of story, Jennings says, just doesn’t pass the smell test for millions of Americans.
“If you’re constantly presenting information in a way that 80 percent of Americans disagree with, doesn’t that inherently drive down your trust levels?” he asks. “You keep saying, ‘You have to believe in this — if you don’t believe in this, you’re bigoted. You have to believe in this — if you don’t believe in this, you’re bad.’ All the while, everyone you know and everyone around you believes these things and holds these very opinions that those in media tell you is beyond the pale.
“And then you see it on your television, and you wonder, what is happening here? It’s like a funhouse mirror, and it’s distorted.”
And that distortion has created a vacuum — one Jennings has almost unwittingly stepped right into, where authenticity rules the day.
Rising on the Right
That realization has certainly been good for Jennings, giving him almost cult-hero status in conservative circles. His popularity has skyrocketed, and he’s become a frequent panelist on CNN, to the point that people begin to wonder whether he’s become a co-anchor.
That visibility is a far cry from June 2017, when CNN first signed him as an on-air political contributor — at the time, one of several GOP communications pros the network rotated through its bench.
Clips of his “confrontations” on the show now live well beyond the hour it is on the air. Almost every time he is on, his work floods social media, being shared all over X and WhatsApp, and finding a second life on YouTube shows and podcasts, which have become increasingly popular as people turn away from traditional media.
(As if to illustrate this, the conversation was interrupted by a passerby who needed to confirm that it was actually Scott Jennings he spotted, and to say hi to him.)
If it feels like he is everywhere, it’s because he almost is. Jennings has become a fixture on the speaking circuit, crisscrossing the country with recent stops in states like Indiana, Florida, Georgia, Utah, Texas, and Minnesota. He headlines events such as the Young America’s Foundation national student conference, the Kansas Chamber of Commerce’s annual dinner, and the National Association of Realtors’ legislative meetings. Audiences often tell him how much they “love the debate” from his CNN appearances — though some seem to enjoy more that he’s “owning the libs.”
He’s accompanied President Trump on Air Force One, has a book coming out that the president himself promoted, and recently signed a three-year contract extension with CNN (whom he has nothing but good things to say about), meaning he will be a part of that family for over a decade. That is, unless he does what a growing number of insiders whisper he should do, and jumps into the Kentucky Senate race to replace retiring majority leader Mitch McConnell, whom he has known personally since the age of 16 and to whom he feels deeply indebted for where he is today.
Perhaps the most interesting part of the Jennings phenomenon is the inherent contradiction he represents. While Jennings is a fresh voice in a world that seems to have moved on and no longer trusts legacy media, he is doing it on possibly the most “legacy” cable news networks that ever existed. It’s almost counterintuitive that he is having the success he has on such a network, when “his people” largely do not have any sort of regard for CNN at all.
It’s been good for CNN too, that’s for sure. Adweek reports that the show he’s most prominently featured on is the network’s top show in the most important demographic, and has grown over 30 percent from the previous year.
Jennings’s success on CNN, a network often viewed skeptically by his audience, underscores the network’s paradoxical strength.
“CNN still matters,” he says.
While trust in legacy media has eroded, CNN’s brand recognition and reliability during crises continue to draw massive audiences. For instance, on Election Day 2020, CNN averaged over two million viewers, its best day in nearly four years, and during the January 6 Capitol riot, it recorded its most-watched day ever with over five million viewers.
These spikes demonstrate that when urgency trumps skepticism, CNN remains the go-to source. Moreover, CNN’s digital platforms extend its reach, facilitating wide exposure and engagement across demographics. This digital presence, coupled with its longstanding reputation, allows CNN to maintain relevance in a fragmented media landscape.
For Jennings, being part of CNN means tapping into this infrastructure and audience, even as he represents a fresh perspective. This synergy between legacy strength and new voices is what makes CNN a valuable platform, he argues, as he leverages its reach to connect with viewers who might otherwise dismiss his message — or the network. The clips of his “highlights” exemplify how CNN can blend its established brand with innovative content, setting the stage for a media model that traditional outlets can adopt to thrive in a digital era.
Jennings’s rising star at the network is evidence of a shift underway at CNN, whose bosses are trying to reposition themselves as a forum for balanced debate rather than an all-liberal shout-fest. It also provides a template for an evolving legacy media, he says, where a place like CNN will still drive the narrative and create primary content for a second life in a digital world.
The outspoken conservative believes that Republicans should engage with that process.
“I don’t believe in conceding these spaces,” Jennings says. “I’ve had some people suggest to me that there’s really no value in being part of the mainstream media. But I just don’t think people with my background and my values can concede or recede at all — because those spaces will ultimately be filled by people who are not of that value set.”
Standing for Sanity
If you’ve ever seen a clip of Jennings on CNN or delivering a speech, you’ve seen the symbol that becomes that much more meaningful in this context of authenticity.
On his left lapel, every single time without fail, Scott Jennings wears the yellow ribbon pin that has become the universal expression of solidarity with those still being held hostage by Hamas in Gaza — irrespective of whether they are in the news or not. The ribbon is not for show; it’s a small act of witness that reflects a worldview grounded in reality, not abstraction. It seems almost curious that someone who was born, raised, and still lives in Kentucky — which isn’t known for its Jewish community by any stretch of the imagination — would embrace that symbol the way he has.
For Scott, there was never any question about it.
“For starters,” he says, “I think what happened on October 7 is the clearest line of demarcation of whether someone can tell right from wrong. I just don’t understand how people are trying to rationalize this or make excuses for it. It’s one of the most awful things that’s happened in our lifetime. It is the clearest front in the war on Western civilization.”
And so he began wearing the ribbon, without fail, every time he is on air (and often even when he isn’t). He does so, he says, “to just send a message that I can tell the difference between right and wrong.
It’s a tangible reminder — on air, on the record — that clarity regarding good and evil isn’t negotiable or performative.
“If we can’t tell the difference,” he says, “between civilization and savagery and barbarism, then we are lost.”
He approached his friend and coworker, Van Jones, and told him his plan, asking him to join him. And join him he did. And since then, every single time either of them is on air, they openly wear the symbol of solidarity with the Jewish people, as we wait desperately for our brothers and sisters still in Gaza to come home.
For a liberal like Jones, it was somewhat harder. He gets intense pushback from the left for it, and clearly, his stance has earned him some enemies. But from Jennings’s point of view, it is well worth it.
“I think it’s great to see one guy on the right and one guy on the left coming together on a clear moral issue. It’s crazy to me that people have looked at this and somehow decided the victims are the bad guys and the bad guys are the victims. Israel’s our ally, the Jewish People are our friends, and the barbarians are at the gate. We’ve got to figure out where we stand.”
The yellow ribbon stays on his lapel even when the headlines move on — a quiet but unmistakable declaration that some truths don’t change with the news cycle — even if it starts to seem so from the coverage.
And that is a problem he can’t solve entirely on his own. The mainstream media constantly misrepresents the opinions of Americans in general, Jennings says, acting as though there are two equal perspectives — or even worse, only one — on issues that the overwhelming majority of Americans see a certain way.
Take, he says, the issue of Israel and the Palestinians, and the conflict with Hamas in Gaza.
“I truly think that the Hamas cheerleaders are way over-indexed on cable news.”
The term he uses, “Hamas cheerleaders,” is not coincidental. It was only March of last year that he came under fire, when following an interview with Ilhan Omar about the Gaza war, for referring to her as “a public relations agent for Hamas sitting in United States Congress.”
He smiles as he recalls that moment. “Oh, they were mad. The whole Squad called for me to be fired and so on and so forth.”
But despite that, he points out — as if to justify the reason for him being at CNN — his employer never wavered and always stood behind him.
What was left, Jennings says, was a teachable moment — and not just about the media.
“What ought to worry us is that so many people are so easily taken in by absolute propaganda and brainwashing,” he says. “That’s number one.”
He points to the recent activity on college campuses as being especially revealing for many Americans who wouldn’t otherwise be exposed to it.
“College campuses are awash in foreign students who have come here with extreme anti-American and anti-Western views, and I fully support Rubio revoking their visas [and removing them]. We don’t need them here. There is no value to importing people who want to destroy our country.”
The bigger picture, he adds, is about how quickly the oldest hatred spreads — and how familiar it feels.
“The real lesson here is how quickly hateful ideology and propaganda can spread — and how right under the surface anti-Semitism always is… look how fast it bubbles up.”
He ties that observation directly to national leadership and campus culture alike. “It was infecting the Democratic Party in the last election. Vice President Harris wouldn’t even go to Prime Minister Netanyahu’s speech to Congress. They’re our ally!… It’s not just random activists or random college kids. It’s bad.”
Recognizing this simple fact, he says, carried with it an immense sense of responsibility. “When you’re in a position of public opinion responsibility like I am,” he reflects, “you cannot equivocate.”
Plucky from Kentucky
Scott Jennings is clearly a media natural, but his path to the CNN studio was anything but a given. He grew up in a poor household in Kentucky. His parents were both laid off from factory jobs; his father worked in a garbage dump, while his stepmother cleaned houses and worked overnight shifts at a gas station just to make ends meet.
A lifeline appeared when, as a high-school senior, he won a full-tuition place in Senator Mitch McConnell’s newly founded McConnell Scholars Program at the University of Louisville. “Without him,” he says, “there’s no Scott going to college.”
Campus bills still had to be paid, so the freshman took an overnight shift at WHAS-AM, a Kentucky radio station. Four years later, as a senior journalism major, he won first place for “Continuing News Coverage” for a radio series on Louisville’s homeless population, who were then living in soon-to-be-demolished stockyards.
“My job as a journalist is to tell people about their world,” he explained in a 2000 interview. “I wanted to shed some light on a group who literally had no place to go,” giving an early hint of the plain-spoken empathy and focus on average Americans that now powers his on-air commentary.
The Kentucky senator and outgoing majority leader gave Jennings his first job in politics. After working on the Bush campaign, Jennings went on to the White House, where he served as a special assistant to President Bush. In 2012, he worked on the Romney campaign and established his own political consulting firm, which has won multiple races in Kentucky. That rags-to-relative-riches background has shaped Scott Jennings’s politics.
“I still have nightmares about my parents, from when I was a kid,” he says, “wondering whether they were going to be able to keep the house. I remember it like it was yesterday. These are seminal moments, and you carry them with you and within you — the way it shapes your worldview and keeps you grounded in how politics affects real people, and how real people analyze these things. So I think it gives me a unique ability to absorb the news and analyze the news from a perspective that a lot of people don’t have.”
Jennings credits his upbringing not just for his perspective, but for the way he connects on air and off. “I don’t look down on my fellow Americans. I do think that’s a problem in politics and media. Sometimes I think we look down on people… I don’t, because those are my people, and I sort of feel responsible to stand up for them and give them some kind of a voice in these venues.”
The diversity in his background took a twist with the rise of Donald Trump. One would not often see a career working for McConnell, Bush, and Romney as part of a natural progression leading to the “most visible defender of the Trump agenda on cable news.”
He says that despite the personal differences his mentors have with the president — and the fact that he hates that they are estranged from each other — he doesn’t see contradiction. In fact, he sees the opposite.
“Working for President Bush… I watched the media paint a caricature of them that simply wasn’t true. Bush was dumb, and Cheney was some Darth Vader character… Then I look at Trump, and I see the way they portray him, and I think they’re doing the same thing.” Jennings admits he’s “somewhat defensive of Trump, actually, over some of the ways he’s caricatured and some of the things he’s called in the media today.”
And McConnell and Trump are “linked in history” if for no other reason than the impact they had — together — on the future of the Supreme Court and standing firm as “a bulwark against the insanity of the left.”
While the elites in politics and media just don’t get how people can regard President Trump as authentic (“people will forgive you your trespasses and people will forgive you your contradictions, and people will forgive you your mistakes if they think you’re being real”), that’s not the only thing they don’t get about this current moment — which Jennings believes he has figured out.
The Republican Party’s traditional coalition — as formed by Ronald Reagan — has been described as the “three-legged stool,” fusing together social conservatives, war hawks, and fiscal conservatives. But Trump has overturned that entirely and reordered the political landscape so that the GOP consists of an eclectic group of people who believe in a new triad: a return to common-sense governance, a defense of Western civilization, and a firm commitment to free speech.
A big part of being authentic, he argues, is recognizing this shift as well. And it’s why the old playbook of attacks are virtually toothless when his interlocutors try coming at him with them on the show. When former New York Times columnist Charles Blow tried to cite a 2016 column Jennings wrote as inconsistent with his support for the president now, he parried it easily.
“I was thinking in that moment that more people read my nine-year-old columns than ever read Charles Blow’s [columns] before he got fired by the New York Times,” Jennings only half jokes. “But it’s true. I was, like a lot of Republicans, not sure what to make of it — it worried me, and I wasn’t trained to understand what he was doing. Honestly, I did not get it, and it took me a while to get it. But I have happily voted for him three times, and this is what I voted for.”
Work in Progress
Like anyone who has adapted himself to the new GOP, assimilating Trumpian ideas has meant having to be flexible on previously unassailable conservative orthodoxy.
“I wasn’t trained to believe tariffs are a good thing… [But] what Trump is trying to do here politically is very interesting. It’s like an organ transplant… he’s grafting new DNA into the party.… I used to think this was super audacious. Now I’m starting to think, ‘Well, is it actually just responsible to try to be responsive to a constituency?’ ”
It is important, he contends, to acknowledge the reality of a changing party. It is also important not to follow the path of those who were previously Republicans but were “broken by Trump” — to the extent that they have now realigned themselves with people inimical to everything they formerly believed, advancing policies and politicians who stand directly athwart everything they always claimed to care about politically.
Interestingly, on tariffs specifically, even if they unnerve him reflexively, Jennings strikes a hopeful and optimistic tone. China, he points out, is “the enemy” and it is in the national interest to deal with them, once and for all. As for the other countries, he is adopting a “wait-and-see” position.
“This man,” he says, referring to President Trump, “was put on the face of this earth to make deals, and now he set up a situation where he has to make deals. So, I guess I have a lot of confidence in that.”
While Jennings acknowledges actual shifts in his own thinking since 2016 — and even since some points during the Biden presidency — he cannot understand the thought process of the people who once identified as conservatives but are now (and forever) “Never Trump.”
“Listen to what their argument was in the election. To save conservatism, you have to vote for Kamala Harris. Man, is that the craziest thing you’ve ever heard? Of course it is!”
There is an interesting parallel to be made, however.
While the Republican Party is more “ideologically elastic,” and it encompasses people from Rand Paul to RFK Jr., and Tulsi Gabbard to Tom Cotton, and, Jennings says, “it doesn’t mean I’m going to always agree with everything everybody says, on the big stuff, I think everybody who’s in this coalition is in full agreement. The left has gone too far here and around the world, and it has to be stopped.”
The Democratic Party has one core and animating issue, and that’s what has drawn these people who once called themselves conservatives into that tent as well.
“I was asked by [CNN anchor] Kasie Hunt, ‘Who do you think is in charge of the Democratic Party?’” he recalls. “I said, ‘I don’t know who’s in charge, but I know who runs it. Donald Trump.’ He runs both parties, ours and theirs. And it’s true, they’re only oriented around him.”
If Trump remains the focal point of American politics, the fulcrum of Scott Jennings’s life is being a father. It elevated his media career, and is also one of his main motivations to continue — after all, he jokes, he will have four college tuitions to pay someday.
“Being a parent,” he says, “means clawing and scraping for every possible opportunity for your children.”
And he will continue to fight anyone who gets in the way of that — whether it is Randi Weingarten or Hamas apologists, every step of the way.
(Originally featured in Mishpacha, Issue 1063)
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