Comparing Roosevelt and Trump

Historian David S. Brown joins the Chuck ToddCast to unpack why Theodore Roosevelt remains a gravitational force for understanding American power—and why his era echoes so loudly today. Drawing from his book In the Arena, Brown explores what pulled him to Roosevelt, how TR reshaped the presidency, and the surprising parallels (and sharp limits) between Roosevelt and Donald Trump. From narcissism and disruption to populism, primaries, and the rise of the imperial presidency, the conversation digs into how Roosevelt’s wealth, ambition, and genuine concern for the working class produced a uniquely transactional style of politics at home and abroad.

The episode also zooms out to ask what Roosevelt might make of modern challenges like AI, extreme wealth concentration, and great-power competition—and whether he’d thrive or flounder in the television age. Brown traces Roosevelt’s foreign policy legacy in Latin America, the roots of American global policing, and how early 20th-century realignments mirror today’s fractured coalitions. The discussion closes with a hard look at the political center, the future of the Trump coalition, under-studied presidents, and how Americans should think about their country as it approaches its 250th anniversary.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 David S. Brown joins the Chuck ToddCast

02:00 Teddy Roosevelt is a magnet for historians

03:15 Research process for writing “In The Arena”

04:30 What drew you to Teddy Roosevelt as a book subject?

07:15 Large number of similarities between Roosevelt and Trump

08:15 Both Trump & Roosevelt are narcissists 

09:15 Trump doesn’t have the crossover appeal of Roosevelt

10:30 Presidential primaries started under Roosevelt

11:45 Roosevelt was the rich guy who went after rich guys

14:00 Roosevelt never called himself a populist

14:30 Roosevelt wanted to do right by the working class

16:00 How would Roosevelt handle AI & concentration of wealth?

17:15 Roosevelt was very transactional in foreign affairs

17:45 He manufactured a separatist movement in Colombia

20:00 America didn’t have power to enforce Monroe Doctrine until 1900

21:15 Roosevelt wanted to police governments in western hemisphere

22:45 Goal was to indebt Latin American countries to the U.S.

23:30 He was always considered a disrupter despite wealthy connections

25:45 Roosevelt became a regular politician in 1884

26:15 Roosevelt was not a fan of William Jennings Bryan

27:45 Roosevelt was jealous of Bryan’s oratory skill

28:45 Would Roosevelt struggle in the TV era?

30:45 The imperial presidency originated under Roosevelt

33:15 Wilson & Roosevelt lamented not leading during seminal event

34:30 A Roosevelt government likely enters WW1 earlier

35:30 Roosevelt might have started the U.N. framework sooner

37:30 Political realignment was happening under Roosevelt

38:15 Parallels between now & Roosevelt era?

40:00 Roosevelt & Trump are mavericks not embraced by old guard

42:00 Multiple variables will affect the future of the “Trump coalition”

44:00 How do you define “the center” in American politics?

45:30 There are more base Republicans than Democrats, Dems need moderates

47:00 How much of the electorate resides in the political center?

48:15 The parties themselves are basically multi-party coalitions

50:15 Which president do we not have enough scholarship on?

54:00 How should citizens celebrate the 250th anniversary of America

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