Intro

On November 20, 1925, Robert Francis Kennedy was born in Brookline, Massachusetts. A hundred years later, Bobby might matter more than ever. Chris Matthews, longtime host of MSNBC’s “Hardball”, is already the author of one bestselling RFK biography, Bobby Kennedy: A Raging Spirit. And today, to celebrate the centennial of his birth, the pugnacious polemicist has a new book about RFK’s abiding relevance. In Lessons From Bobby, Chris Matthews gives us ten reasons why Robert Francis Kennedy still matters. Matthews’ favorite lesson? Bobby’s willingness to concede defeat. After losing the 1968 Oregon Democratic primary to Gene McCarthy, Kennedy graciously acknowledged his loss and paid tribute to his opponent. Matthews argues this is essential to democracy. “The loser is the only one who can give credential to the winner,” he notes. “Without that, the American people always have doubts.” Yes, in November 2025, Bobby matters more than ever.

1. Bobby’s Vulnerability Was His Strength Unlike JFK’s aloof, almost royal demeanor, Bobby identified with victims rather than observing them from a distance. He “seemed to have identified with people’s troubles and thought of himself as one of the victims,” making him relatable in ways his more polished brother never was.

2. Personal Experience Transformed His Politics Bobby’s commitment to civil rights deepened dramatically after his assistant John Seigenthaler was beaten nearly to death during the Freedom Rides in 1961. “Something turned in him,” Matthews notes—he realized someone close to him had been left to die in the streets, radicalizing his approach to racial justice.

3. The Kennedys Became Liberals Strategically Neither Jack nor Bobby started as liberals. After narrowly losing the 1956 VP nomination, JFK realized “I got a lot of Southern support, but I don’t have any liberal support.” The Kennedys understood that power in the Democratic Party was liberal, so they “married” figures like Arthur Schlesinger and John Kenneth Galbraith to reposition themselves.

4. Bobby Could Separate Good from Bad Matthews emphasizes Bobby’s ability to “granulate the good from the bad”—whether distinguishing corrupt labor bosses like Jimmy Hoffa from reform leaders like Cesar Chavez, or understanding how riots after King’s assassination could be both morally motivated and criminally wrong. This nuanced thinking set him apart.

5. Conceding Defeat Defines Democracy Matthews’ most important lesson: Bobby’s gracious concession after losing Oregon to Gene McCarthy exemplifies democratic virtue. “The loser is the only one who can give credential to the winner,” Matthews argues, contrasting this sharply with Trump’s 2020 election denial and warning that without honest concessions, “the American people always have doubts.”

Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe