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

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

Keen On America

June 5, 2026

“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?
Speakers: Andrew Keen, Evan Thomas
**Andrew Keen** (0:00)
Hello, my name is Andrew Keen. Welcome to Keen On America, the daily interview show about the United States.
Hello, everybody, we're on the road today in Washington, DC in conversation with an old friend of the show, Evan Thomas, a distinguished American writer, historian, commentator, last on the show talking about his book about President Truman and his decision to bomb Hiroshima. He's also the author of one of my favorite books, certainly my favorite biography of Robert Kennedy, His Life, which came out in 2000 Evan, welcome back to the show. Why did you write this Bobby Kennedy book? It certainly wasn't the first or the last biography.

**Evan Thomas** (1:04)
Endlessly fascinating person. I mean, it's hard to find a more interesting person in 20th century American politics than Bobby Kennedy because he's a Kennedy but also because of who he was. I thought I can't write that because Arthur Schlesinger has written the biography of Bobby Kennedy. But Walter Isaacson, actually, a friend of mine and co-author of mine, said, no, no, no, the world is ready for another Bobby thing. Also Schlesinger, who was brilliant, was too close to Bobby. He was practically a member of the Kennedy family.
There's room for another and there was. So I spent three or four years reporting and wrote the book.

**Andrew Keen** (1:44)
You say he's one of the most interesting men in 20th century American history. What does that mean to be an interesting man, Evan?

**Evan Thomas** (1:52)
Well, it means that he's torn between conflicting impulses. One is a power impulse. He's a Kennedy raised by his father to exercise raw power. And he was pretty good at that and pretty harsh about it and pretty ruthless about it. At the same time, mid-century American, he's discovered iniquity and race.
He's discovered that our wonderful country was not living up to its own constitution and its own heritage, and he wanted to make things better. And he really, he didn't just say it, he met 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.

**Andrew Keen** (2:42)
He used the word interesting.
Other words come to mind as well, heroic, tragic. There is a heroic, tragic quality to his life. Well, there was. Is that fair?

**Evan Thomas** (2:57)
Absolutely. He loved heroes. I mean, he was always an actor on his own stage because he was fascinated with heroes, and he was fascinated with the idea of courage. There was no more important word to him in the English language than courage.
What did Churchill say? That's the greatest virtue because without it, you can't have the others.
So he believed that. I believe in physical courage, emotional courage, mental courage, and he wanted to be an actor on the stage. It was complicated because he starts out as the helper of his brother. He's the behind the scenes guy. He's not on stage. He's behind the scenes making it happen. Then his brother Jack dies. Suddenly, he's got to be front and center. This was hard for him. It wasn't natural for him. But in his own kind of awkward, touching way, he embraced it. And just at the time he was killed, he was coming into it.

**Andrew Keen** (3:51)
Where does courage come from? Where did it come from in Bobby? I know you spent some time with Robert Cole, his psychologist friend, a man who gave Bobby Kennedy's inner life a great deal of thought professionally and personally.
Is courage a consequence of dysfunctionality?

**Evan Thomas** (4:10)
Yes, I mean, courage comes from suffering. Real courage comes from being afraid.
And when Bobby was little, he was afraid. He was a runty little boy, sort of down at the wrong end of the dinner table. The good end of the dinner table with the father is Jack and Joe and Kick. They're the golden kids.

**Andrew Keen** (4:31)
The golden trio.

**Evan Thomas** (4:32)
The golden trio. Down at the other end of the table with the nuns and mom and all that are the other kids. Bobby was the runty one, regarded himself as a loser. He gets kicked out of prep school for cheating.
He's not the athlete. He's not as good looking. So he suffers as a kid. He has to overcome a lot. And that is a source of courage because it took courage just to overcome being a loser.

**Andrew Keen** (4:59)
What was it, Evan, about physical courage that marks Bobby out? Of course, in your book, you write about a number of remarkable episodes. And he did the 50-mile walk. He climbed Mount Kennedy in plimsolls, never having trained. This seems to be an astonishing quality.

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