Scott Jennings: The Kentucky Kid Who Conquered Politics
If you’ve ever flipped on CNN and seen a guy with a sharp suit and sharper opinions holding his own against a panel of talking heads, chances are you’ve caught Scott Jennings in action. At 47, he’s a political strategist, commentator, and writer who’s as comfortable in the halls of Washington as he is back home in Kentucky. His story is one of grit, smarts, and a knack for knowing what makes people tick whether they’re voters, viewers, or CEOs. So, who is Scott Jennings, and how did a kid from Dawson Springs end up shaping the Republican playbook? Let’s break it down.
Growing Up in the Heartland
Born on October 26, 1977, in Princeton, Kentucky, Scott grew up in nearby Dawson Springs, a speck on the map in Western Kentucky. Think rolling hills, pickup trucks, and diners where the coffee’s always brewing. It’s the kind of place that sticks with you, and for Scott, it shaped his worldview hard work, community, and a no-nonsense approach to life. He was curious from the get-go, the kind of kid who’d rather ask “why” than just go along.
In high school, Scott found his voice literally through journalism. He started working in radio, and by the time he got to the University of Louisville, he was already a pro. As a McConnell Scholar (yep, named after that Mitch McConnell), he studied political science, graduating in 2000. But he wasn’t just hitting the books he was on the air at WHAS Radio, anchoring news and reporting stories. One series on Louisville’s homeless community even snagged him an Associated Press award. Young Scott was already showing he could tell stories that hit home, a skill that’d serve him well in politics.
Kicking Off a Political Career
Scott didn’t waste time after college. In 2000, at just 23, he jumped into the deep end as the political director for George W. Bush’s presidential campaign in Kentucky. Now, Kentucky wasn’t exactly a swing state, but it had gone for Bill Clinton twice, so flipping it red was no small feat. Scott helped Bush pull it off, winning 56.5% of the vote. That win put him on the map as a guy who could get things done.
From there, it was like Scott was playing political pinball, racking up wins. In 2002, he ran Mitch McConnell’s re-election campaign, and the senator crushed it with 65% of the vote a Kentucky record. A year later, Scott was the political director for Ernie Fletcher’s gubernatorial run, helping him become the state’s first Republican governor in over 30 years. By 2004, Scott was in New Mexico, running Bush’s re-election campaign in a state Al Gore had won by a razor-thin 366 votes. The local Republican Party was a mess think resignations and infighting but Scott and his buddy Jay McCleskey turned it around. They recruited 15,000 volunteers, built a grassroots machine, and flipped New Mexico red. That’s the kind of hustle that gets you noticed.
White House Days
Scott’s work in New Mexico was his ticket to the big leagues. In 2005, he landed a gig in the White House as an associate director in the Office of Political Affairs, working under Karl Rove, the mastermind behind Bush’s campaigns. By October, he was promoted to special assistant to the president and deputy director of political affairs. His job? Be the glue between the White House, Congress, and local leaders. He also had a hand in getting Supreme Court Justices John Roberts and Samuel Alito confirmed pretty heady stuff for a guy in his late 20s.
There was a small hiccup in 2007 when Scott’s name popped up in a report about a General Services Administration meeting. The Office of Special Counsel said the GSA head, Lurita Doan, broke the Hatch Act by mixing politics with government business during a briefing Scott attended. But the report didn’t pin anything on Scott himself his presentation was standard White House fare, and the Bush team brushed it off as business as usual. It was a blip, not a scandal, and Scott kept moving forward.
From Politics to PR and Punditry
After his White House stint, Scott headed back to Kentucky, joining Peritus Public Relations in Louisville as a senior strategist. In 2012, he co-founded RunSwitch Public Relations with some partners, and it’s now the biggest PR firm in the state. RunSwitch isn’t just about politics they work with Fortune 25 companies, handling everything from media strategy to crisis management. Scott’s secret sauce? He’s got a politician’s gut for what people care about and a data nerd’s love for crunching numbers.
Around the same time, Scott started writing. In 2013, he kicked off a column for the Louisville Courier-Journal, which often gets picked up by USA Today. His pieces cut through the noise, tackling politics and policy with a clear, conservative lens. In 2018, he won a Society of Professional Journalists award for his work proof he’s got a way with words. That same year, he joined CNN as a political contributor, stepping into the lion’s den of cable news. Whether he’s debating policy or sparring with liberal pundits, Scott’s cool-headed and quick on his feet. The Washington Free Beacon even dubbed him their 2024 “Man of the Year” for his ability to “own the libs” without breaking a sweat.
Scott’s media game doesn’t stop at CNN. He writes for the Los Angeles Times, CNN.com, and RealClearPolitics, and he’s a regular on Fox News and MSNBC. In 2022, he launched Flyover Country with Scott Jennings, a podcast where he chats politics with big names like McConnell, Daniel Cameron, and Erick Erickson. It’s a love letter to Middle America, blending national issues with a heartland perspective.
Still in the Political Trenches
Even with his media gigs, Scott’s never left the campaign trail. He’s advised McConnell in three more races (2008, 2014, 2020), worked with Congressman Brett Guthrie since 2008, and ran Mitt Romney’s Ohio operations in 2012. In 2014 and 2016, he helped a Super PAC called Kentuckians for Strong Leadership, which dropped millions to keep McConnell in the Senate and flip the Kentucky House red for the first time in 100 years. He also advised Jeb Bush in 2015 and produced ads for Daniel Cameron’s 2019 attorney general race, helping make history as Cameron became Kentucky’s first Black statewide officeholder.
Scott’s also giving back through teaching. Since 2018, he’s been an adjunct lecturer at Harvard’s Kennedy School, teaching a course on modern American politics. He’s a fellow at the University of Chicago’s Institute of Politics and has taught at Tufts, too. His classes dive into campaigns, tribalism, and how to talk politics in a polarized world stuff he’s lived firsthand.
Life Outside the Spotlight
Scott’s not just a political wonk he’s a family man. He’s married to Autumn Stiff from Whitesville, Kentucky, and they’ve got four boys: Everett, Winston, Thatcher, and Harlan. They live in Prospect, Kentucky, where they’re raising chickens and looking after a basset hound named Rufus and a parakeet called Luna. It’s the kind of life that keeps Scott grounded, even when he’s jetting to D.C. or L.A.
He’s also big on community. Scott’s on the boards of the Louisville Forum and Leadership Louisville, and he’s been part of Leadership Kentucky and the Bingham Fellows. For all his national clout, he’s still a Kentucky guy at heart.
The Haters and the Fans
Scott’s got his critics, like anyone in the public eye. Some folks on X have grumbled that he’s flipped on issues like calling Trump a threat one day and defending him the next to score media points. But those claims are thin, and in today’s polarized world, that kind of noise comes with the territory. On the flip side, conservatives like Dan Bongino cheer Scott for standing tall in “enemy territory” on CNN, delivering Republican talking points with clarity and guts.
What’s Next for Scott Jennings?
At 47, Scott’s nowhere near done. He’s got his hands in everything campaigns, PR, media, teaching and he’s showing no signs of slowing down. His podcast is growing, his columns keep sparking conversation, and his political instincts are as sharp as ever. Whether he’s shaping the next big Republican win or breaking down the news for millions, Scott Jennings is a force. He’s proof that you can come from a small town, stay true to your roots, and still play ball on the national stage. Here’s to watching where this Kentucky kid goes next.
If you’ve ever flipped on CNN and seen a guy with a sharp suit and sharper opinions holding his own against a panel of talking heads, chances are you’ve caught Scott Jennings in action. At 47, he’s a political strategist, commentator, and writer who’s as comfortable in the halls of Washington as he is back home in Kentucky. His story is one of grit, smarts, and a knack for knowing what makes people tick whether they’re voters, viewers, or CEOs. So, who is Scott Jennings, and how did a kid from Dawson Springs end up shaping the Republican playbook? Let’s break it down.
Growing Up in the Heartland
Born on October 26, 1977, in Princeton, Kentucky, Scott grew up in nearby Dawson Springs, a speck on the map in Western Kentucky. Think rolling hills, pickup trucks, and diners where the coffee’s always brewing. It’s the kind of place that sticks with you, and for Scott, it shaped his worldview hard work, community, and a no-nonsense approach to life. He was curious from the get-go, the kind of kid who’d rather ask “why” than just go along.
In high school, Scott found his voice literally through journalism. He started working in radio, and by the time he got to the University of Louisville, he was already a pro. As a McConnell Scholar (yep, named after that Mitch McConnell), he studied political science, graduating in 2000. But he wasn’t just hitting the books he was on the air at WHAS Radio, anchoring news and reporting stories. One series on Louisville’s homeless community even snagged him an Associated Press award. Young Scott was already showing he could tell stories that hit home, a skill that’d serve him well in politics.
Kicking Off a Political Career
Scott didn’t waste time after college. In 2000, at just 23, he jumped into the deep end as the political director for George W. Bush’s presidential campaign in Kentucky. Now, Kentucky wasn’t exactly a swing state, but it had gone for Bill Clinton twice, so flipping it red was no small feat. Scott helped Bush pull it off, winning 56.5% of the vote. That win put him on the map as a guy who could get things done.
From there, it was like Scott was playing political pinball, racking up wins. In 2002, he ran Mitch McConnell’s re-election campaign, and the senator crushed it with 65% of the vote a Kentucky record. A year later, Scott was the political director for Ernie Fletcher’s gubernatorial run, helping him become the state’s first Republican governor in over 30 years. By 2004, Scott was in New Mexico, running Bush’s re-election campaign in a state Al Gore had won by a razor-thin 366 votes. The local Republican Party was a mess think resignations and infighting but Scott and his buddy Jay McCleskey turned it around. They recruited 15,000 volunteers, built a grassroots machine, and flipped New Mexico red. That’s the kind of hustle that gets you noticed.
White House Days
Scott’s work in New Mexico was his ticket to the big leagues. In 2005, he landed a gig in the White House as an associate director in the Office of Political Affairs, working under Karl Rove, the mastermind behind Bush’s campaigns. By October, he was promoted to special assistant to the president and deputy director of political affairs. His job? Be the glue between the White House, Congress, and local leaders. He also had a hand in getting Supreme Court Justices John Roberts and Samuel Alito confirmed pretty heady stuff for a guy in his late 20s.
There was a small hiccup in 2007 when Scott’s name popped up in a report about a General Services Administration meeting. The Office of Special Counsel said the GSA head, Lurita Doan, broke the Hatch Act by mixing politics with government business during a briefing Scott attended. But the report didn’t pin anything on Scott himself his presentation was standard White House fare, and the Bush team brushed it off as business as usual. It was a blip, not a scandal, and Scott kept moving forward.
From Politics to PR and Punditry
After his White House stint, Scott headed back to Kentucky, joining Peritus Public Relations in Louisville as a senior strategist. In 2012, he co-founded RunSwitch Public Relations with some partners, and it’s now the biggest PR firm in the state. RunSwitch isn’t just about politics they work with Fortune 25 companies, handling everything from media strategy to crisis management. Scott’s secret sauce? He’s got a politician’s gut for what people care about and a data nerd’s love for crunching numbers.
Around the same time, Scott started writing. In 2013, he kicked off a column for the Louisville Courier-Journal, which often gets picked up by USA Today. His pieces cut through the noise, tackling politics and policy with a clear, conservative lens. In 2018, he won a Society of Professional Journalists award for his work proof he’s got a way with words. That same year, he joined CNN as a political contributor, stepping into the lion’s den of cable news. Whether he’s debating policy or sparring with liberal pundits, Scott’s cool-headed and quick on his feet. The Washington Free Beacon even dubbed him their 2024 “Man of the Year” for his ability to “own the libs” without breaking a sweat.
Scott’s media game doesn’t stop at CNN. He writes for the Los Angeles Times, CNN.com, and RealClearPolitics, and he’s a regular on Fox News and MSNBC. In 2022, he launched Flyover Country with Scott Jennings, a podcast where he chats politics with big names like McConnell, Daniel Cameron, and Erick Erickson. It’s a love letter to Middle America, blending national issues with a heartland perspective.
Still in the Political Trenches
Even with his media gigs, Scott’s never left the campaign trail. He’s advised McConnell in three more races (2008, 2014, 2020), worked with Congressman Brett Guthrie since 2008, and ran Mitt Romney’s Ohio operations in 2012. In 2014 and 2016, he helped a Super PAC called Kentuckians for Strong Leadership, which dropped millions to keep McConnell in the Senate and flip the Kentucky House red for the first time in 100 years. He also advised Jeb Bush in 2015 and produced ads for Daniel Cameron’s 2019 attorney general race, helping make history as Cameron became Kentucky’s first Black statewide officeholder.
Scott’s also giving back through teaching. Since 2018, he’s been an adjunct lecturer at Harvard’s Kennedy School, teaching a course on modern American politics. He’s a fellow at the University of Chicago’s Institute of Politics and has taught at Tufts, too. His classes dive into campaigns, tribalism, and how to talk politics in a polarized world stuff he’s lived firsthand.
Life Outside the Spotlight
Scott’s not just a political wonk he’s a family man. He’s married to Autumn Stiff from Whitesville, Kentucky, and they’ve got four boys: Everett, Winston, Thatcher, and Harlan. They live in Prospect, Kentucky, where they’re raising chickens and looking after a basset hound named Rufus and a parakeet called Luna. It’s the kind of life that keeps Scott grounded, even when he’s jetting to D.C. or L.A.
He’s also big on community. Scott’s on the boards of the Louisville Forum and Leadership Louisville, and he’s been part of Leadership Kentucky and the Bingham Fellows. For all his national clout, he’s still a Kentucky guy at heart.
The Haters and the Fans
Scott’s got his critics, like anyone in the public eye. Some folks on X have grumbled that he’s flipped on issues like calling Trump a threat one day and defending him the next to score media points. But those claims are thin, and in today’s polarized world, that kind of noise comes with the territory. On the flip side, conservatives like Dan Bongino cheer Scott for standing tall in “enemy territory” on CNN, delivering Republican talking points with clarity and guts.
What’s Next for Scott Jennings?
At 47, Scott’s nowhere near done. He’s got his hands in everything campaigns, PR, media, teaching and he’s showing no signs of slowing down. His podcast is growing, his columns keep sparking conversation, and his political instincts are as sharp as ever. Whether he’s shaping the next big Republican win or breaking down the news for millions, Scott Jennings is a force. He’s proof that you can come from a small town, stay true to your roots, and still play ball on the national stage. Here’s to watching where this Kentucky kid goes next.
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