Could Caribbean Territories Form a U.S. State?

On this episode of the Chuck ToddCast, Chuck breaks down the latest in Washington as the government shutdown nears its end—and the political fallout begins. Democrats have shown more backbone than expected, while Donald Trump’s strategy has Republicans quietly questioning his grip on power. From his push to cut SNAP benefits for his own voters to his increasingly distorted view of the economy, Trump’s disconnect from reality is starting to cost him. Chuck also looks at the Democrats’ strong showing in the recent elections, what it says about voter sentiment heading into 2026, and whether we’re witnessing the beginning of Trump’s lame duck era. Plus, the ripple effects of Trump’s policies—from affordability to the upcoming World Cup—and what Mike Johnson’s loyalty to Trump means for the GOP’s future.

Then, Chuck sits down with journalist and historian Garrett Graff, host of The Long Shadow, to unpack how America’s political scandals—from Watergate to Trump—have shaped the presidency and public trust. Graff reflects on the slow process of uncovering the truth about Nixon’s 1968 interference and how those lessons apply to Trump’s open defiance of the Presidential Records Act. The two dive into why history takes decades to judge leaders, how government secrecy really works, and why even the most shocking revelations—like Iran-Contra or January 6th—take years to fully understand.

Graff also discusses the ripple effects of past scandals, from Monica Lewinsky’s mistreatment to the rise of political figures forged during the Clinton impeachment, and how the legacy of Trump may take a generation to contextualize. The conversation ends on the future of media itself—how O.J. Simpson changed television forever, how algorithms broke the internet, and what it means for truth in an age where everyone’s chasing clicks.

Finally, Chuck hops into the ToddCast Time Machine to revisit the surrender of the Ottoman Empire after World War 1 and the lasting implications for peace in the middle east, answers listeners’ questions in the “Ask Chuck” segment and breaks down the weekend in college football.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Chuck Todd’s introduction

00:30 End of the government shutdown seems imminent 

02:15 Democrats have had a stiffer spine than expected

03:00 Surprising that Trump fought to cut SNAP, many were his voters

04:30 Trump ran on protecting benefits, has done the opposite during shutdown

05:15 Trump keeps claiming the economy is better than it is

06:00 Is Trump in an information bubble that’s not giving him reality?

07:00 Trump being out of touch is making Republicans start to distance from them

08:45 Mamdani’s election was not “the most important” result

09:45 New Jersey governor result was more revealing than Mamdani’s

10:30 Democrats win in Nov 4th election showed it was a referendum on Trump

12:00 Democrats should take the win and cut a deal to end shutdown

13:00 Are we entering the lame duck period of Donald Trump’s presidency?

14:45 Trump’s handling of the shutdown has been terrible politics for Republicans

16:15 The affordability message penetrated, culture war didn’t at all

17:30 Trump’s policies are creating a mess ahead of the 2026 World Cup

19:00 Trump is more focused on his image rather than affordability

19:45 Some Republicans are realizing they’ll have to break with Trump

22:15 Mike Johnson has basically become Donald Trump’s puppet

23:30 Trump is either losing his grip on reality, or trying to remake it

25:00 Trump falling asleep in meetings is a big deal

35:15 Garrett Graff joins the Chuck ToddCast 

37:15 Getting started with The Long Shadow podcast 

38:15 The importance of going back and covering recent history 

41:00 Looking at pivotal, fork in the road moments in history 

44:30 It took 50 years to answer two central questions about Watergate 

47:15 Extent of Nixon's treachery in '68 wasn't exposed until recently 

48:30 Watergate led to destruction of White House taping system 

50:15 Trump is actively skirting the Presidential Records Act 

52:45 Mike Johnson excuses Trump's corruption because it's in the open 

54:15 Thoughts on looking back into Iran Contra? 

56:45 CIA afraid that copping to Oswald could unravel other bad actions? 

58:30 History says that meddling in Venezuela will go extremely poorly 

59:45 Government conspiracies presuppose limited competence 

1:00:30 Government can keep big secrets briefly or small secrets a long time 

1:03:15 Is there more to be covered on Monica Lewinsky & impeachment? 

1:04:45 No greater victim in a scandal than Lewinsky, Clinton's never apologized 

1:07:15 Much of the Supreme Court got their start with Clinton impeachment 

1:08:15 The view of presidents changes greatly over the decades 

1:10:15 Judging past presidents relative to poor recent leaders 

1:12:15 The politics of the author color presidential biographies 

1:14:45 The historical telling of January 6th won't be ripe until Trump dies 

1:15:45 There are so many January 6th villains whose stories must be told 

1:16:45 Chuck's "Love/Hate" relationship with Roger Stone 

1:17:45 The best way to interview a serial liar 

1:19:15 The only good sources around Trump always remain anonymous 

1:21:15 How worried are you about the future of American democracy? 

1:22:00 We're underestimating how bad things are 9 months into Trump 

1:23:45 We'll never be the country we were before Trump, but still reason for hope 

1:24:45 Trump has a strong grip on a weak hand 

1:26:30 Don't know whether we're in the beginning, middle or end of Trump story 

1:27:45 Trump is too lazy to build a lasting movement 

1:29:30 Democrats won't admit that Trump voters aren't wrong about some things 

1:30:45 Democrats put asterisks next to elections they lost to Trump 

1:33:45 Any interest in covering anything outside of politics? 

1:34:45 OJ Simpson fundamentally changed the TV news business 

1:37:30 Chasing ratings made the audience the editor for TV news 

1:38:15 What Garrett is working on - Why algorithms broke the internet

1:46:15 Chuck's thoughts on interview with Garrett Graff 

1:47:15 November 11th, 1918 World War 1 ends 

1:48:00 Surrender of Ottoman Empire is largely forgotten, hugely consequential 

1:49:00 Terms of surrender were incredibly harsh 

1:49:45 European powers began carving up the middle east 

1:50:30 Europe stopped fighting, the middle east didn't 

1:52:00 In the US, World War 1 is only taught as a prequel to WW2 

1:53:00 WW1 is the reason the middle east is still a mess today 

1:55:00 We need to improve how we teach the history of World War 1 

1:56:00 Ask Chuck 

1:56:15 Can you explain why the senate has 60 vs. 50 vote thresholds? 

2:01:30 Should the Virgin islands join with other islands to become a state?

 2:02:30 Love for the election night livestream 

2:03:45 Why haven't the 2026 federal appropriations been approved? 

2:06:15 Chuck's experience at Vets for Tech event 

2:15:30 College football reaction

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