Composed Jack versus emotional Bobby

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
Nobody asks more impertinent questions than the Anglo-American writer, filmmaker and Silicon
Valley entrepreneur Andrew Keen. In Keen On America , Andrew brings his sharp Transatlantic
wit to the forces reshaping the United States — hosting daily interviews with leading thinkers
and writers about American history, politics, technology, culture, and business. With nearly
2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most
prolific intellectual interview show in the history of podcasting.
Website | Substack | YouTube