“He didn’t just say it, he meant it, he felt it — and the combination of the power guy, the ruthless power guy, and the profound idealist was fascinating, and also hard for him.” — Evan Thomas on Bobby Kennedy

Who was the greatest riddle in 20th century American political life? Judging from the ever-expanding library of Bobby biographies, Robert Francis Kennedy ranks very high on that list. Indeed, according to Evan Thomas, one of RFK’s most acclaimed biographers, this third Kennedy son is, indeed, the most sphinx-like riddle in 20th century America.

In his classic 2000 biography, Robert Kennedy: His Life, Thomas unravels the good and the bad Bobby. But, rather than presenting parallel narratives, his portrait treats the Machiavellian and the idealist as the same riddle. Raised by his father to exercise raw power, RFK discovered that mid-century America wasn’t living up to its own ideals. The contradiction of the ruthless Kennedy machine politician and the profound idealist was what continues to make him so intriguing to Americans of every political stripe.

Bobby concurred with Churchill’s dictum that courage is the greatest virtue because, without it, you can’t have the other virtues. So he lived a life of ridiculous physical and moral courage — taking insane risks that would terrify ordinary mortals. And, of course, his most insanely courageous act was his last — running for President in 1968 knowing that he was likely to be assassinated. Where have you gone, Bobby Kennedy? A nation turns its lonely eyes to you.

Five Takeaways

• The Central Paradox. The ruthless Kennedy machine politician and the profound idealist were the same man. Raised to be the henchman. Genuinely felt the injustice he found in mid-century America. Permanently at war with his own nature. That’s what made him so fascinating.

• Courage: The Only Word That Mattered. Churchill: it’s the greatest virtue, because without it you can’t have the others. Bobby believed it. Runty kid at the wrong end of the dinner table. Kicked out of prep school. Real courage comes from suffering. It took courage just to overcome being the loser.

• Making Up for Missing the War. Jack is a war hero. Joe dies trying to replicate it. Bobby scrapes a destroyer deck in the Caribbean. He spends the rest of his life making up for it — swimming the Colorado River, jumping overboard to save Jack’s jacket. Sometimes stunts. Increasingly, moral courage.

• The Mob, Joe Kennedy, and the Beehive. Poking around in the mob as Senate aide: Hoover points out it leads back to Joe Kennedy. Whether conscious or unconscious rebellion, Bobby starts grazing against his own father. Hoover uses it to blackmail the Kennedys. It never fully landed. But it started.

• The Ripple of Hope, and RFK Jr. as Tragedy. South Africa, 1966: every time somebody does something brave, it causes a ripple. Margaret Marshall was in the audience. He gave us hope where there was none. Hickory Hill today: nothing. RFK Jr.: his own family has disavowed him. Caroline accused him of crimes. The idea of Robert Kennedy Jr. is tragic.

About the Guest

Evan Thomas is an American writer and historian, former Washington bureau chief of Newsweek, and the author of Robert Kennedy: His Life (Simon & Schuster, 2000) and nine other books. His Churchill biography is forthcoming in December 2026.

References

Robert Kennedy: His Life by Evan Thomas (Simon & Schuster, 2000): simonandschuster.com/books/Robert-Kennedy/Evan-Thomas/9780743203296
Bobby Kennedy’s Ripple of Hope speech, Cape Town, June 6, 1966

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:

00:00:30 Introduction: Andrew in Washington DC
00:01:34 Why write another Bobby Kennedy biography?
00:02:22 The central paradox: power guy and idealist
00:03:27 Courage: the most important word
00:04:40 The runty kid at the wrong end of the dinner table
00:05:29 Making up for missing the war
00:07:11 Not valuing his own life
00:09:04 Taking on his father: the mob investigations
00:11:00 Hoover blackmails the Kennedys
00:25:00 JFK’s assassination and Bobby’s transformation
00:31:39 Hickory Hill: the ghost of Camelot
00:33:08 The ripple of hope speech
00:34:24 RFK Jr.: tragic and disavowed
00:37:21 Bobby Kennedy and the Shakespearean epithet
00:37:21 Churchill biography out December 1, 2026