“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. Cunningham won South Carolina’s 1st Congressional District in 2018 — a seat Trump had carried by 13 points, the first Democrat to hold it in forty years. He was also the first elected Democrat to publicly warn against Biden seeking re-election. His prescriptions come from someone who has actually won where Democrats can’t win.
• The Party Replaced Empathy with Arrogance. Told people the economy was fine when they couldn’t afford their bills. Dismissed concerns about immigration and crime as bigotry. Told West Virginia that immigration wasn’t its issue. The party stopped listening and started lecturing. Voters left.
• Big Publishing’s Progressive Insularity. The book was too critical of the Democratic Party for major publishers. Cunningham published it himself. Andrew’s observation: isn’t this itself evidence of what the book argues?
• The Geriatric Oligarchy and Tech. Most members of Congress can’t grapple with AI, social media, or data centres. The party needs leaders who understand these problems. Community-level decisions, not blanket bans. Proper regulation: liberty to wolves is death to lambs.
• The Party Needs Bloodletting. After the debate, Democratic officials said Biden was fine. His staff said he’d go to bed earlier. Cunningham’s verdict: lessons will be repeated until they’re learned. The party needs a genuine coming-to-Jesus moment, not bloodless triangulation.
About the Guest
Joe Cunningham is a personal injury attorney and former US Representative from South Carolina’s 1st Congressional District. He is the author of Life of the Party (South Battery Press, May 20, 2026). Available at lifeofthepartybook.com.
References
Life of the Party by Joe Cunningham (South Battery Press, May 20, 2026): lifeofthepartybook.com
About Keen On America
Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen.
Website: https://keenon.tv/ Substack: https://keenon.substack.com/ YouTube: https://youtube.com/@KeenOnShow
Chapters:
00:00:31 Introduction: Natapoff’s Harvard Law vs Cunningham’s Charleston
00:01:44 Harvard was my safety school
00:02:18 Americans don’t like either party
00:03:02 What’s wrong with the Democrats?
00:03:55 Winning a Trump +13 district
00:04:15 Why big publishing didn’t pick up the book
00:05:51 America as an arc of justice
00:07:09 Charleston and the Civil War
00:15:00 Immigration: the issue in West Virginia
00:25:00 Bidenomics: the economy is fine
00:30:00 The debate and Democratic officials outside the White House
00:35:00 Gerrymandering
00:41:01 Technology, AI, and the geriatric oligarchy
00:44:06 The midterms: bloodletting within the party
00:45:15 A coming-to-Jesus moment
00:46:16 A Joe Cunningham run in 2028?
00:46:59 Number one in elections on Amazon