Comparing Roosevelt and Donald Trump

In this episode of the Chuck ToddCast, Chuck unpacks what may be the most brazen presidential corruption scandal in modern history—Donald Trump allegedly selling U.S. foreign policy to the UAE for personal gain—barely registered in the public conversation, drowned out by louder, more sensational distractions. The discussion explores why Trump’s election-interference rhetoric breaks through while substantive corruption stories vanish, how media incentives favor spectacle over consequence, and why Trump responds selectively to political, market, and institutional pressure. Chuck argues that while some democratic guardrails still hold, the deeper danger isn’t a dramatic coup but the slow erosion of norms—one where kleptocracy becomes normalized, foreign policy is treated as a personal asset, and Congress, not voters, remains the only institution capable of stopping it before the damage becomes irreversible.

Then, Historian David S. Brown joins Chuck 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.

Finally, Chuck gives his ToddCast Top 5 states Democrats need to target prior to 2032, when census reapportionment will greatly change the electoral college math needed to win the presidency and answers listeners’ questions in the “Ask Chuck” segment. 

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Chuck Todd’s introduction

02:00 Worst presidential corruption scandal ever couldn’t break through

03:15 Trump sold American foreign policy to UAE for personal gain

04:15 Story was jaw dropping, but was completely overshadowed

05:30 Trump’s threat to federalize elections broke through over corruption

06:30 Should you worry about what Trump is saying, or what he’s doing?

07:30 Trump is desperate to sell the lie that he won in 2020

08:15 Election inference rhetoric can be as powerful as election interference

09:30 Trump shutdown Kennedy Center because he was being humiliated

10:45 Trump was losing control of Kennedy Center narrative, made a spectacle

11:45 Trump has turned America into a kleptocracy, THAT should be the story

13:15 The corruption story disappeared from news cycle after a couple days

14:00 Editors lean on stories that get more traction rather than importance

15:00 Some of the guardrails still work, some of the time

15:45 After two deaths in Minneapolis, Trump backed down a bit

16:30 Trump does respond to political pain in polling

17:00 Trump didn’t pick a sycophant for Fed Chair, cares about markets

17:45 Trump responds to three types of pressure

19:30 Worried less about Trump’s election rhetoric than his foreign policy

20:00 Trump doesn’t have the power to override state elections

20:45 Trump’s election threats supercharge opposition turnout

21:30 Voters won’t be the check on corruption, congress has to be

22:30 Democracies don’t fall from coups, they erode

23:15 The scariest stories get attention, the most consequential get ignored

27:45 David S. Brown joins the Chuck ToddCast

29:45 Teddy Roosevelt is a magnet for historians

31:00 Research process for writing “In The Arena”

32:15 What drew you to Teddy Roosevelt as a book subject?

35:00 Large number of similarities between Roosevelt and Trump

36:00 Both Trump & Roosevelt are narcissists

37:00 Trump doesn’t have the crossover appeal of Roosevelt

38:15 Presidential primaries started under Roosevelt

39:30 Roosevelt was the rich guy who went after rich guys

41:45 Roosevelt never called himself a populist

42:15 Roosevelt wanted to do right by the working class

43:45 How would Roosevelt handle AI & concentration of wealth?

45:00 Roosevelt was very transactional in foreign affairs

45:30 He manufactured a separatist movement in Colombia

47:45 America didn’t have power to enforce Monroe Doctrine until 1900

49:00 Roosevelt wanted to police governments in western hemisphere

50:30 Goal was to indebt Latin American countries to the U.S.

51:15 He was always considered a disrupter despite wealthy connections

53:30 Roosevelt became a regular politician in 1884

54:00 Roosevelt was not a fan of William Jennings Bryan

55:30 Roosevelt was jealous of Bryan’s oratory skill

56:30 Would Roosevelt struggle in the TV era?

58:30 The imperial presidency originated under Roosevelt

1:01:00 Wilson & Roosevelt lamented not leading during seminal event

1:02:15 A Roosevelt government likely enters WW1 earlier

1:03:15 Roosevelt might have started the U.N. framework sooner

1:05:15 Political realignment was happening under Roosevelt

1:06:00 Parallels between now & Roosevelt era?

1:07:45 Roosevelt & Trump are mavericks not embraced by old guard

1:09:45 Multiple variables will affect the future of the “Trump coalition”

1:11:45 How do you define “the center” in American politics?

1:13:15 There are more base Republicans than Democrats, Dems need moderates

1:14:45 How much of the electorate resides in the political center?

1:16:00 The parties themselves are basically multi-party coalitions

1:18:00 Which president do we not have enough scholarship on?

1:21:45 How should citizens celebrate the 250th anniversary of America?

1:25:00 Chuck’s thoughts on the interview with David S. Brown

1:25:30 Democrats will lose seats after 2030 census

1:28:00 Parties can work for realignment & flipping states

1:28:45 House of Representatives needs to be doubled in size

1:30:15 Base voters expect immediate results, leaders need to think long-term

1:30:45 Democrats need a Project 2032 and invest to win 5–10 new states

1:31:30 ToddCast Top 5 states Democrats should be targeting NOW

1:32:30 #1 North Carolina

1:35:00 #2 Texas

1:36:45 #3 Kansas

1:38:45 #4 Georgia

1:39:45 #5 Arizona

1:40:15 Honorable mentions

1:41:30 Democrats should use “first in the nation” primary status to advantage

1:42:15 Democrats had 12 states submit for first in the nation status

1:44:15 Tennessee as first in the nation would be interesting

1:46:15 Tennessee’s electorate seems gettable for Democrats eventually

1:48:30 Democrats have a major problem come 2032 if they don’t address it now

1:49:15 Ask Chuck

1:49:30 Thoughts on moving from network to independent journalist?

1:53:45 How to avoid being fatigued by the news and keeping hope alive?

1:54:15 Trump threatening troops to protect Iranians while attacking Minnesota?

1:59:00 What’s your take on NIL & transfer portal in college football?

2:03:30 Basis for your confidence in Jon Ossoff & thoughts on Auburn coach?

2:08:00 What issues will be top of mind for voters leading into midterms?

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