Weekend Plans is our exclusive lifestyle feature where we highlight the real off-duty routines of the most exciting people in culture.
The Daily Wire recently caught up with Scott Jennings at a bistro in Washington, D.C., just a stone’s throw from the Capitol. America’s self-proclaimed “favorite pundit,” Scott has made a name for himself as CNN’s contrarian (read: conservative) voice since 2017. When he’s not working to make level heads prevail, he’s at home in Kentucky raising four boys and 38 chickens. We talked about those press secretary rumors, stumping AI Teddy Roosevelt, and undertaking the not-so-simple task of saving Western civilization.
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Scott Jennings doesn’t normally dress up for Halloween, but he’s got an idea of who he could go as this year. And it’s only scary if you’re afraid of the truth.
“I might just try to dress up like the most rational person I can,” he quips.
It takes some guts to be the guy whom everyone else on live television is yelling at, but Scott doesn’t seem to mind. He enjoys being the one bringing some levity to the roundtable.
“I like the debates,” he says. “I like the debates when the debaters are good faith and informed and have some good nature about it. You know, a lot of people in politics these days are joyless. They never smile. They can’t make a joke or take a joke. It just gets a little tedious. The other night I was on TV, and these people were losing their minds about some AI video that Marsha Blackburn had sent out. You’d have thought we were on the brink of the apocalypse over it.”
Despite the “humorless scolds,” Scott is more of a happy warrior.
“Every single topic must be used to browbeat the joy out of you,” he says. “And I’m just determined not to let that happen.”
Scott Jennings
Having survived the Blackburn-pocalypse, Scott Jennings is on a mission to make common sense great again. When I mention the rumors that the White House could be considering him for the press secretary position, he demurs.
“I’ve read about it,” he says. “I haven’t spoken to anybody about it, and my only advice to them is I don’t think [President Donald Trump] needs to do anything before the election. And he needs to find the most credible, qualified, and capable person that he can.”
Between navigating the midterm election results and the final years of Trump’s second term, the press secretary will need to be “pretty skillful,” he adds.
Trump “is going to need all the help he can get, in my view,” Scott says. “And he deserves it. He’s the president, and the American people deserve a credible, qualified messenger to stand up there and set the record straight when necessary and give people information that maybe they wouldn’t otherwise get.”
Born In The Bluegrass State
Jennings isn’t like other pundits — at least, not the ones who spend their days taking the Acela between New York City and Washington. He’s spent much of his life in Kentucky, where he was born, attended college (at the University of Louisville), and has lived since 1996. The way he pronounces “Louisville” (loo-ah-vohl) tells you he’s not faking it.
He married his wife, Autumn Stiff Jennings, in 2010, and the couple has four boys: 17-year-old Everett, a senior in high school who wants to be a park ranger; 13-year-old Winston, a musician and lead singer in a band; 11-year-old Thatcher, who loves basketball, Legos, and chess (and has beaten his father “only occasionally”); and 9-year-old Harlan, who plays soccer.
All four boys attend different schools, which makes mornings pretty hectic. Throw in three dozen “laying hens,” and Scott is relying on a lot of coffee. His 68-year-old father lives in the Jennings household and helps with the chaos. The boys can be found playing driveway basketball or watching the St. Louis Cardinals lose. (“We’re having a bit of a disappointing run right now,” Scott laments.)
Somehow, he still finds time for the chickens, which have been a part of the family since 2020.
We get down to the nitty-gritty: He talks about his standard white Leghorns, Golden Laced Wyandotte (“It’s a beautiful chicken”), and Silver Laced Wyandotte (“which is also a beautiful chicken”), and shows me pictures.
Scott Jennings
“That’s my main hobby,” he admits. “I go home, and I take care of my chickens … It’s been a rewarding hobby, and the whole family participates in it. And we eat some of the eggs, and we give a lot of eggs away. Back when eggs were so expensive, we were very popular.”
There are no roosters, and that’s intentional.
“We got a rooster once by accident, and I learned two things: one, they crow all day, not just in the morning, and [two] they constantly sexually harass their coworkers,” Scott shares. “So, we actually named our rooster Governor Cuomo. But we impeached the governor.”
The People’s Pundit
Jennings keeps his easy manner while talking about pretty much anything, from chickens to his favorite presidents: Teddy Roosevelt and Abraham Lincoln, who, people forget, was born in Kentucky. Even when Scott is coming to your TV live from New York City, his bluegrass roots keep him grounded.
“I think having a family, living in Middle America, and experiencing our politics with that lifestyle is pretty unique in the punditry business,” he says, “and it’s good for family-focused Middle Americans to have somebody on TV that sees the world the way they do — not that we necessarily would all share politics, but we certainly share life experience, and that I think that matters a lot.”
Most American families are not going to waste their energy whining about an AI campaign ad. They’re too busy shuttling their kids to school — or in Scott’s case, four schools.
“I think sometimes that’s my job: to sit down there on the end of contrarian corner and maybe put a little dose of Middle America reality into these conversations about whether people would care about this or not,” he says.
He also travels the country constantly, and one of his top non-chicken-related hobbies is visiting national parks. His family marks their progress in a “passport book” with stamps from each park, and he guesses he’s been to at least 30. True to his love for the great outdoorsman, Scott speaks fondly of Theodore Roosevelt National Park, and he made it to the opening of the Theodore Roosevelt Presidential Library earlier this year.
Scott Jennings
This is where he stumped AI Teddy Roosevelt. Programmed to speak like the president based on his speeches, books, and other writings, the life-size avatar answers questions from curious visitors. But it missed a bit of trivia about Kentucky.
“I asked if he had any thoughts on the people of Kentucky or visiting Kentucky,” Scott says. “And he said, ‘Hmm, I don’t think I’ve ever had a proper tour of Kentucky,’ which is not true, because he did come to Kentucky right at the end of his presidency and laid the cornerstone of the Abraham Lincoln Birthplace Memorial.”
Jennings reported the error to the programmer at the library, whom he has also interviewed on his radio show. She quickly checked and returned to tell him he was correct. And when he’s right, Scott isn’t afraid to show it.
“I think there should be a plaque in that room noting that I corrected the AI,” he says.
This encyclopedic knowledge comes from listening, learning, and reading a lot of presidential biographies. To prepare to do battle on CNN, Scott treats his job like that of a reporter, reading voraciously and getting on the phone with sources.
“I want as much information as I can get to make the best argument that I can,” he says. “When you have five people yelling at you at the same time, you cannot afford to show up unprepared.”
Western Civ 101
Like the rest of us, Scott has been enjoying the Marco Rubio memes. But it’s the secretary of state’s recent speech about Western civilization that he finds truly inspiring. As rioters tear down monuments to Western greatness in Paris, Scott worries that kind of devastation could be coming stateside.
“Look at what’s happening in France and Italy right now, and ask yourself, do you want that in America? Because my view is they’re just a few steps ahead of us on the road to perdition here,” he says. “These aren’t school protests! These are people who are trying to overthrow the West.”
As far as the midterms go, this might not be a kitchen-table issue, but it may be the thing that keeps the kitchen table from being demolished.
“They’re destroying buildings that are hundreds of years old,” he says. “They’re destroying art. I mean, they are destroying the evidence of our culture and our own Western history. So, I think the defense of this is going to be at the center of our politics, and it’s the opposite of a day-to-day concern for a voter, but if you don’t get that right, what else do you have?”
Scott takes seriously his role in shaping national conversation, and this is the issue that, despite their infighting, he believes conservatives can address together.
“And so whatever differences Conservative A might have with Conservative B,” Scott says, “the thing that’s knitting us together in many cases is we’re all mortified at the idea that the West would crumble, and we’re committed to doing something about it.”
