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
01:10 What Has Happened to America?
03:40 The One-Third Fracture
05:15 Elections as the Great Solver
07:30 An Intellectual Aristocracy
10:45 The Romance of Camelot
14:20 Bobby’s Vulnerability
17:45 Touch Football at Hickory Hill
20:30 Jackie vs. Hickory Hill
22:15 Composed Jack, Emotional Bobby
24:40 The Assassinations
28:15 Could Bobby Have Won?
30:30 The Kennedys and Internationalism
34:00 Chris Matthews and the Bobby Kennedy Centenary
36:30 The Perpetual Civic Duty
38:45 Closing
Links & References
Mentioned in this episode:
Act of Creation: The Founding of the United Nations by Stephen Schlesinger
https://www.stephenschlesinger.com/act-of-creation/
A Thousand Days: John F. Kennedy in the White House by Arthur Schlesinger Jr.
https://bookshop.org/p/books/a-thousand-days-john-f-kennedy-in-the-white-house-arthur-m-schlesinger/2d20d4bf175b02e6
Robert Kennedy: His Life by Evan Thomas
https://bookshop.org/p/books/robert-kennedy-his-life-evan-thomas/e3f537554ba7c80a?ean=9780743203296&next=t
Bobby Kennedy: A Raging Spirit by Chris Matthews
https://bookshop.org/p/books/bobby-kennedy-a-raging-spirit-chris-matthews/e605247e875df9ed?ean=9781501111877&next=t
The Power and the Glory by Graham Greene — the novel Bobby Kennedy mentioned reading at a 1967 dinner Schlesinger attended
https://bookshop.org/p/books/the-power-and-the-glory-graham-greene/10575d6868dd30d4?ean=9780143107552&next=t
Why England Slept by John F. Kennedy (1940)
https://bookshop.org/p/books/why-england-slept-john-f-kennedy/5ce2f82362f43c39?ean=9798350501667&next=t
Previous episode: Andrew Guthrie Ferguson on Your Data Will Be Used Against You (Episode 2794)
https://www.keenon.tv/your-data-will-be-used-against-you-andrew-guthrie-ferguson-on-policing-in-the-age-of-self-surveilla/
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: https://www.keenon.tv/
Substack: https://keenon.substack.com/
YouTube: youtube.com/@KeenOnShow