“I deliver it with the credibility of having won a district that Trump carried by 13 points. Not only how to speak to these voters, but how to win them back.” — Joe Cunningham

Yesterday’s guest was Alexandra Natapoff, co-editor of America Unfinished — a collection of essays by illustrious Harvard Law School professors grading the march toward justice in the United States over the last 250 years. America got about a C+ from this progressive clique. “Could do better” their report cards suggested.

Today’s guest is a very different kind of Democrat. Joe Cunningham is a lawyer and personal injury attorney in Charleston, South Carolina, a one-term US representative, and the author of Life of the Party: How Democrats Lost America’s Trust and How They Can Win It Back. Cunningham got his law degree at Northern Kentucky University’s Salmon P. Chase College of Law. Harvard, he jokes, was his safety school.

In contrast with Harvard Law professors, Cunningham’s credibility is hard to dress up. He was the first Democrat to win South Carolina’s 1st Congressional District in over forty years, in a seat Trump carried by 13 points. He was also the first Democrat in elected office to publicly warn against Biden seeking re-election. His diagnosis of what went wrong is that the Democratic Party abandoned kitchen-table economic issues in favour of culture wars, dismissed legitimate voter concerns as bigotry, and told people what they should care about rather than listening to what they actually cared about. The party, he argues, replaced empathy with arrogance. It’s as if it’s been colonized by morally prickly Harvard Law professors. Professor Cunningham gives the Dems a D+. Could do significantly better.

Five Takeaways

• Winning Trump +13: The Credibility Argument: Cunningham’s case for why his diagnosis should be taken seriously is not his ideology but his record. He won South Carolina’s 1st Congressional District in 2018 — a heavily gerrymandered seat that Trump had carried by 13 points — making him the first Democrat to hold it in over forty years. He was also the first elected Democrat to publicly warn against Biden seeking re-election. His prescriptions don’t come from a think tank or an op-ed page. They come from a man who has actually won where Democrats can’t win, and lost where Democrats keep losing.

• The Party Replaced Empathy with Arrogance: Cunningham’s central diagnosis: the Democratic Party stopped listening and started lecturing. It told people what they should care about — immigration wasn’t an issue in West Virginia because West Virginia is far from the border. It told people the economy was fine when they couldn’t afford their bills. It dismissed legitimate concerns about crime, immigration, and cultural change as bigotry rather than trying to understand them. The result: voters who felt condescended to left. The party that was founded on speaking for ordinary people no longer speaks their language.

• Big Publishing’s Progressive Insularity: The book didn’t get picked up by a major publisher. Cunningham was told, more or less directly, that a book this critical of the Democratic Party — of Biden, of Harris, of the party’s leadership — was too much. He published it himself, through South Battery Press, named for a street in Charleston. Andrew’s observation: isn’t this itself evidence of what the book argues? If progressive culture controls big media and big publishing, those institutions will inevitably filter out self-criticism and reinforce the insularity that caused the problem in the first place.

• The Geriatric Oligarchy and the Technology Frontier: Cunningham uses the phrase “geriatric oligarchy” — the same phenomenon Andrew has been calling a gerontocracy — to describe Congress’s inability to grapple with technology, AI, and social media. The vast majority of members of Congress cannot understand the problems that are emerging: social media preying on children, identity theft, artificially inflated prices, the environmental impact of data centres. The party needs new leaders who understand these issues. The answer to data centres is not a blanket ban — it’s community-level decisions and proper regulation.

• The Party Needs Bloodletting, Not Just Rebrand: Cunningham’s sharpest prescription for the Democratic Party: a coming-to-Jesus moment or genuine accountability for what led to 2024. After the debate, Democratic officials stood outside the White House claiming Biden was fine. His staff said he’d go to bed earlier, wake up later, and shorten his workday — as if this would reassure Americans. Cunningham’s verdict: lessons will be repeated until they’re learned. The party needs a Newsom-level confrontation — real winners and real losers — not the bloodless triangulation it currently offers. Only then can it earn back trust.

About the Guest

Joe Cunningham is a personal injury attorney and former US Representative from South Carolina’s 1st Congressional District, the first Democrat to win that seat in nearly forty years. An attorney and ocean engineer by training, he was the Democratic nominee for Governor of South Carolina in 2022. He is the author of Life of the Party: How Democrats Lost America’s Trust and How They Can Win It Back (South Battery Press, May 20, 2026). He lives in Charleston, South Carolina, with his wife Ashley and their children.

References:

• Life of the Party: How Democrats Lost America’s Trust and How They Can Win It Back by Joe Cunningham (South Battery Press, May 20, 2026). Available at lifeofthepartybook.com.

• Episode 2922: Alexandra Natapoff on America Unfinished — the preceding episode referenced at the opening; the Harvard Law contrast.

• Episode 2912: Michael Clinton on Longevity Nation — the gerontocracy argument directly referenced.

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.

Chapters:

(00:31) - Introduction: Natapoff’s Harvard Law vs Cunningham’s Charlesto...