Keen On America

What kind of leadership can hold a fractured democracy together?
About the Guest
Stephen Schlesinger is an American historian, author, and foreign policy analyst. The son of Arthur Schlesinger Jr.—Pulitzer Prize–winning historian and special assistant to President John F. Kennedy—and grandson of Arthur Schlesinger Sr., he grew up at the centre of one of America's most distinguished intellectual families. Schlesinger is the author of Act of Creation: The Founding of the United Nations, and has written widely on American foreign policy and international institutions. He knew both John and Robert Kennedy personally, and brings a rare insider perspective to the history of American liberalism.
About This Episode
"He went around the table asking us, 'Do you still believe in God?' — this was 1967, he was already being considered for the presidency. Why would a man of this intensity and ambition be talking about these issues?" - Stephen Schlesinger
After two days exploring the surveillance state and the ethics of unmasking—with Andrew Guthrie Ferguson on how your data will be used against you and Christopher Mathias on the fight to expose the radical right—Andrew Keen steps back to ask a larger question: What kind of leadership can hold a fractured democracy together?
Stephen Schlesinger joins the show from the Upper West Side of New York to offer a historian's perspective—and a personal one. From his father's role in Camelot to his own memories of playing touch football with Bobby Kennedy at Hickory Hill, Schlesinger reflects on what made the Kennedy brothers effective leaders in a divided country, and what lessons their example holds for progressives today. The conversation moves from the founding of the republic (one-third pro-British) through the Civil War to the present fracture, and asks whether elections remain democracy's "great solver"—or whether something has fundamentally changed.
Chapters:
00:00 Introduction
 On the road in New York, beside Columbia University
01:10 What Has Happened to America?
 Schlesinger’s 250-year view of national fracture
03:40 The One-Third Fracture
 Why a leader with minority support cannot impose ideology on 330 million
05:15 Elections as the Great Solver
 Except for the Civil War, the ballot box has resolved every American crisis
07:30 An Intellectual Aristocracy
 Harvard, the Schlesinger legacy, and the view from inside the American elite
10:45 The Romance of Camelot
 Meeting JFK, the magnetism of youth, and the television presidency
14:20 Bobby’s Vulnerability
 The dinner where RFK asked, “Do you still believe in God?”
17:45 Touch Football at Hickory Hill
 Bobby’s toughness and the bullet pass Schlesinger had to catch
20:30 Jackie vs. Hickory Hill
 Two styles of Kennedy parenting
22:15 Composed Jack, Emotional Bobby
 Arthur Schlesinger Jr.’s perspective on the two brothers
24:40 The Assassinations
 The White House, Lyndon Johnson’s motorcade, and the bar exam Schlesinger failed
28:15 Could Bobby Have Won?
 Humphrey, the nomination, and what might have been
30:30 The Kennedys and Internationalism
 From Joe Kennedy’s isolationism to JFK’s UN vision and RFK during the Cuban Missile Crisis
34:00 Chris Matthews and the Bobby Kennedy Cenentary
Lessons for Today
36:30 The Perpetual Civic Duty
Why each generation must defend constitutional freedoms anew
38:45 Closing
Advice to grandchildren and the enduring fight for democracy
Links & References
Mentioned in this episode:
Act of Creation: The Founding of the United Nations by Stephen Schlesinger
A Thousand Days: John F. Kennedy in the White House by Arthur Schlesinger Jr.
Robert Kennedy: His Life by Evan Thomas
Bobby Kennedy: A Raging Spirit by Chris Matthews
The Power and the Glory by Graham Greene — the novel Bobby Kennedy mentioned reading at a 1967 dinner Schlesinger attended
Why England Slept by John F. Kennedy (1940)
Previous episode: Andrew Guthrie Ferguson on Your Data Will Be Used Against You (Episode 2794)
About Keen On America
Keen On America is a daily podcast hosted by Andrew Keen, the Anglo-American writer and Silicon Valley insider named by GQ magazine as one of the world’s “100 Most Connected Men.” Every day, Andrew brings his sharp Transatlantic wit to the forces reshaping the United States — interviewing leading thinkers and writers about American history, politics, technology, culture, and business. With nearly 2,800 episodes since the show’s founding on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website | Substack | YouTube

A man was convicted by his own heartbeat — and that's just the beginning of our digital dystopia.

About the Guest
Andrew Guthrie Ferguson is Professor of Law at George Washington University Law School and a national expert on surveillance technologies, policing, and criminal justice. He is an elected member of the American Law Institute and the author of the PROSE Award–winning The Rise of Big Data Policing. His new book, Your Data Will Be Used Against You: Policing in the Age of Self-Surveillance (NYU Press, March 2026), examines how smart devices and digital surveillance are transforming criminal prosecution — and what the law must do to catch up.
About This Episode
Following yesterday’s conversation with Christopher Mathias about doxxing and the ethics of unmasking, Andrew Keen turns to the legal side of the same question: what happens when the data we generate about ourselves becomes evidence? Andrew Guthrie Ferguson joins the show from Washington, D.C. to discuss his new book — a deeply researched investigation into how pacemakers, smartphones, smart cars, and doorbell cameras are being used to convict people in court, and why the law has almost nothing to say about it.
The conversation moves from a man convicted by his own heartbeat to AI-powered real-time crime centres, from Eric Schmidt’s infamous privacy defence to masked ICE agents in Minneapolis, and from Bentham’s panopticon to Ferguson’s proposed “tyrant test” — a framework for designing data protections by imagining the worst leader with access to your most intimate information.
Chapters:
00:00 Introduction: Digital privacy and unmasking
The theme of digital privacy and what it means to be unmasked in a data-driven world
01:25 Meet Andrew Guthrie Ferguson
 Introducing the guest and his new book on privacy, surveillance, and the law
02:10 The Dual-Edged Sword of Digital Devices
 How our everyday devices expose everyone and the complicated trade-offs that creates
03:40 From “Don’t Be Ashamed” to Privacy Nuance
 The shift from early Silicon Valley privacy optimism to a more complex reality
04:45 Regulating Government, Not Google
 Ferguson’s focus on keeping personal data out of court rather than off corporate servers
05:55 The Pacemaker Data Court Case
 How personal medical device data was used as evidence in a criminal trial
07:30 Convicted by His Own Heartbeat
 An arson and insurance fraud case where heart-rate data contradicted the suspect’s story
09:40 Google’s Three-Part Warrant System
 How tech companies helped shape rules for law enforcement access to location data
11:15 The Fourth Amendment Digital Gap
 What reasonable expectations of privacy mean in the modern digital environment
12:45 Digital Privileges and Intimate Data
 Whether certain types of personal data should be legally protected like confidential relationships
14:20 Surveillance Battles on the Ground
 Protests, law enforcement, and the evolving intelligence dynamic in Minneapolis
16:05 “Just Doing Our Job” and State Surveillance
 The common defence of surveillance practices and why it remains controversial
18:10 The Texas Drone Fleet
 Drones as first responders and the expansion of aerial policing technology
20:45 Real-Time Crime Centers and Mass Cameras
 Integrated camera networks, data fusion, and the lack of clear oversight
22:50 The Tyrant Test for Privacy Laws
 Designing privacy protections assuming the worst possible leader has access to the data
25:15 AI Supercharges Surveillance
 How artificial intelligence turns ordinary cameras into powerful tracking tools
27:30 AI-Assisted Police Reports
 Using body-camera audio and AI tools to generate reports and the implications for justice
29:10 No Turning Back From Technology
 Why abandoning digital tools isn’t realistic and why new laws may be needed instead
31:15 Closing: Every Smart Device Is Surveillance
 The idea that modern connected devices inherently function as surveillance tools

Links & References

Mentioned in this episode:
Your Data Will Be Used Against You — NYU Press
Andrew Guthrie Ferguson — GW Law School faculty page
Perplexity for Public Safety — free AI tool for law enforcement
Previous episode: Christopher Mathias on To Catch a Fascist (Episode 2793)
Carpenter v. United States (2018) — Supreme Court ruling on cell-site location data and the Fourth Amendment

About Keen On America
Keen On America is a daily podcast hosted by Andrew Keen, the Anglo-American writer and Silicon Valley insider named by GQ magazine as one of the world’s “100 Most Connected Men.” Every day, Andrew brings his sharp Transatlantic wit to the forces reshaping the United States — interviewing leading thinkers and writers about American history, politics, technology, culture, and business. With nearly 2,800 episodes since the show’s founding on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website | Substack | YouTube

An anti-fascist spy handed American officials evidence of murderous intent from a Nazi planning server — and they declined to act.

About the Guest
Christopher Mathias is a journalist covering the far right, formerly a senior reporter at HuffPost, with work appearing in The Guardian, The Nation, MSNBC, Zeteo, and WNYC. His reporting has helped unmask white supremacist cops, soldiers, teachers, and politicians, and he was a Deadline Awards finalist for feature writing. He is originally from Gettysburg, Pennsylvania and lives in New York. His new book, To Catch a Fascist: The Fight to Expose the Radical Right (Atria Books), is out now.

About the Episode
Days after Jonathan Rauch’s influential Atlantic essay announced he’d moved from fascism skeptic to fascism believer, Christopher Mathias joins the show to discuss his new book — a deeply reported investigation into the decentralized network of anti-fascist activists who infiltrate, monitor, and expose neo-Nazis and white supremacists operating in positions of power across America.
The conversation quickly moves beyond whether Trump is a fascist to the harder questions his book raises: Who gets to decide who is exposed? What rights to privacy do members of extremist groups retain? Is unmasking community self-defense or vigilantism? And does the same logic that justifies exposing a neo-Nazi EMT extend to the tens of thousands of ICE agents now conducting raids on American streets?
Timeline
00:00 Introduction
 Jonathan Rauch’s Atlantic essay and the renewed fascism debate
01:10 Meet Christopher Mathias
 Introducing the book and the journalist behind it
01:45 The Greenville Moment
 When Mathias first used “fascist” in a headline after watching Trump whip a crowd into chanting “Send her back”
02:40 Defining the F-Word
 Fascism as a right-wing politics of domination; Langston Hughes recognizing it in the 1930s before the word arrived
04:15 The Hard Question
 If MAGA is a fascist movement, are the 70-plus million who voted for Trump fascists too?
05:55 The Worst of the Worst
 Why the book targets explicit neo-Nazis in positions of power, not ordinary Trump supporters
08:15 Who Decides?
 Privacy, accountability, and whether everyone at Charlottesville deserves exposure
10:45 Antifascist Amnesty
 Leave the movement and we leave you alone; return and we publish
12:30 The Equivalence Trap
 Why Mathias rejects the idea that this is just radicals exposing radicals
14:05 From Neo-Nazis to ICE
 How anti-fascist tactics are now used to identify masked federal agents
17:15 Where Does It End?
 Drawing lines between violent enforcement and bureaucratic participation
19:40 “Just Following Orders”
 Why some orders shouldn’t be followed, and the occupation of Minneapolis
21:30 The Battle Over Shame
 Competing databases, surveillance, and what America should be ashamed of
23:15 The Spy Who Warned Charlottesville
 An infiltrator uncovers plans for violence that officials ignore
26:00 Minneapolis as Model
 “We protect us” and a blueprint for grassroots resistance
28:45 The Underground War
 Intelligence, counterintelligence, and the personal cost of exposure
30:30 Closing
 Fascism as a snake eating its own tail and the urgent task of limiting the damage

Links & References

Mentioned in this episode:
Jonathan Rauch, “Yes, It’s Fascism” — The Atlantic (January 2026)
To Catch a Fascist: The Fight to Expose the Radical Right by Christopher Mathias (Atria Books, February 2026)
Christopher Mathias reporting archive
Follow Christopher Mathias: BlueSky | X

About Keen On America
Keen On America is a daily podcast hosted by Andrew Keen, the Anglo-American writer and Silicon Valley insider named by GQ magazine as one of the world’s “100 Most Connected Men.” Every day, Andrew brings his sharp Transatlantic wit to the forces reshaping the United States — interviewing leading thinkers and writers about American history, politics, technology, culture, and business. With nearly 2,800 episodes since the show’s founding on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website | Substack | YouTube

Can meat save the planet? That’s the paradoxical promise of the longtime vegan activist Bruce Friedrich, founder of the Good Food Institute. In his new book, Meat, Friedrich argues that plant-based and cultivated meat can satisfy the craving of the most hardline carnivore while simultaneously fixing the apocalyptic environmental consequences of industrial farming. So new tech, particularly the latest technology that magically mimics meat, will enable the regeneration of the (real) natural world. For this vegan advocate of meat, this next agricultural revolution will not only transform humanity’s favorite food but also our planet’s environmental future. 
Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

There’s something absurdly Strangelovian about the American quest for a perfect weapon. As Jeffrey Stern warns in The Warhead, his new history of The Paveway, the first “smart” bomb, weapons are always, like their human engineers, imperfect. “It’s always exploding somewhere,” Stern dryly notes, and those explosions in the Texas Instruments developed Paveway were not only unexpected, but often tragically imperfect. So for example, the Second Gulf War was the most precise air war in history and yet within a year, more civilians died than in Hiroshima and Nagasaki combined. The conceit of “perfection”, Stern warns, might be as quintessentially American as the fatally flawed Walt Disney corporation or the Kennedy dynasty (both part of the Paveway story). Which is why this history of smart weapons makes such chilling reading in an AI age when Americans are once again being promised perfect military technology. 
Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe