Good Bobby, Bad Bobby: Evan Thomas on the Greatest Riddle in 20th Century American Politics

“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: Power Guy and Idealist in the Same Man: Bobby Kennedy was raised by his father to be the henchman of the Kennedy machine — doing the dirty stuff in Boston politics to keep Jack floating free and grand. He was pretty ruthless about it. At the same time, in mid-century America, he discovered that the country was not living up to its own constitution, and he wanted to make things right, and genuinely felt it. The combination of the machine politician and the profound idealist was what made him so endlessly fascinating. It also made him hard for himself: a man permanently at war with his own nature. • Courage: The Only Word That Mattered: No word was more important to Bobby Kennedy than courage. Churchill: it’s the greatest virtue, because without it you can’t have the others. Kennedy believed in physical courage, emotional courage, mental courage. He was a runty little kid at the wrong end of the dinner table — Jack and Joe and Kick at the golden end with the father, Bobby with the nuns and the mum. He got kicked out of prep school for cheating. He was not the athlete, not the golden one. Real courage comes from suffering. It took courage just to overcome being the loser. That was the source. • Making Up for Missing the War: Physical and Moral Courage: Bobby missed World War Two, basically. He got in at the very end and ended up scraping the deck of a destroyer in the Caribbean, far from combat. His brother Jack is a war hero on steroids — PT boat cut in half by a Japanese destroyer, rescues his men, written about in The New Yorker and Reader’s Digest . Joe volunteers for a secret dangerous mission to replicate Jack’s glory and dies. Pretty high bar of courage. Bobby spends the rest of his life making up for it — swimming the Colorado River, climbing Mount Kennedy in the Yukon, jumping overboard off the coast of Maine to save Jack’s jacket. Sometimes stunts. But increasingly, moral courage — which is the greater thing. • The Mob, Joe Kennedy, and the Beehive: When Bobby starts poking around in the mob as a Senate aide, J. Edgar Hoover is only too happy to point out: keep going here, you know where it’s going to end up. With Joe Kennedy. Bobby’s investigation of Giancana and Frank Sinatra starts grazing against his own father. Thomas’s reading: whether conscious or unconscious, there is an element of rebellion. Bobby, appointed henchman, doing the dirty stuff for pop, resenting it, starts poking the beehive that might expose him. It never fully landed. But it started. And Hoover used it to blackmail the Kennedys. • The Ripple of Hope, and RFK Jr. as Tragedy: Bobby’s trip to South Africa — apartheid everywhere, the freedom movement barely existing, everybody in prison. His speech: every time somebody does something brave or heroic, it causes a ripple, and that gives you hope. A young Margaret Marshall, later Chief Justice of the Massachusetts Supreme Judicial Court, was in the audience. He gave us hope where there was none. That is the ghost Andrew went looking for at Hickory Hill and didn’t find. The contrast with RFK Jr. is, for Thomas, simply sad. Poignant. His own family has disavowed him. Caroline Kennedy made a broadcast accusing him of crimes. The idea of Robert Kennedy Jr. is tragic. About the Guest Evan Thomas is an American writer and historian. He was Washington bureau chief of Newsweek for ten years and a writer and editor there for thirty-three years. He is the author of ten books, including Robert Kennedy: His Life (Simon & Schuster, 2000), Being Nixon , Road to Surrender , and, with Walter Isaacson, The Wise Men . He has taught at Harvard and Princeton. His biography of Churchill is forthcoming from Simon & Schuster in December 2026. References: • Robert Kennedy: His Life by Evan Thomas (Simon & Schuster, 2000). • The Wise Men by Evan Thomas and Walter Isaacson (Simon & Schuster, 1986) — referenced in the closing. • Robert Coles — Bobby Kennedy’s psychologist friend, referenced in the conversation. • Hickory Hill, McLean, Virginia — the Kennedy family home Andrew visited on this trip to Washington DC. • Bobby Kennedy’s “Ripple of Hope” speech, University of Cape Town, South Africa, June 6, 1966. About Keen On America Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America , Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 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

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Good Bobby, Bad Bobby: Evan Thomas on the Greatest Riddle in 20th Century American Politics is an episode from Keen On by Andrew Keen.

This episode is 37:48 long.

This episode was published on Jun 5, 2026.

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