Would Reagan Approve of Trump?

On this episode of the Chuck ToddCast, Chuck reacts to Democrats outperforming expectations across the board in Tuesday’s elections — from New Jersey to Georgia — signaling a sharp political rebuke of Donald Trump and his influence over the GOP. He breaks down why the results were more than just a good night for Democrats, how high electric bills and cost-of-living concerns shaped key races, and why even Republican strongholds are starting to shift. With Trump’s tariffs facing likely Supreme Court scrutiny and voters blaming Republicans for the government shutdown, this week’s results could reshape not just the midterm landscape but the future of both parties.

D.C. representative Oye Owolewa and Executive Director for Puerto Rico 51st George Laws Garcia join Chuck Todd for a deep dive into one of America’s most overlooked democratic debates — the fight for statehood for Washington, D.C. and Puerto Rico. With over 3 million Americans lacking full representation in Congress, Chuck explores the political, constitutional, and cultural hurdles standing in the way. From Puerto Rico’s 58% support for statehood to the District’s struggle under federal oversight, the episode unpacks how history, partisanship, and outdated systems continue to stall progress.

The conversation dives into whether D.C. and Puerto Rico would need to enter as a political “duo”, why half measures like expanded autonomy wouldn’t hold up, and how the economic and tax inequalities faced by both territories have real-world consequences. With bipartisan murmurs of support and the next generation of lawmakers pushing the issue, Chuck asks: is America finally ready to welcome its 51st — and maybe 52nd — states?

Finally, he answers listeners’ questions in the “Ask Chuck” segment and previews the upcoming weekend in college football. 

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Chuck Todd’s introduction

07:30 Tuesday’s elections went even better than expected for Democrats

09:00 Ciaterreli hit all his targets from 2021 and still got blown out

12:00 High electric bills could have resulted in Dem wins in Georgia

15:00 Election results were a repudiation of Donald Trump

16:45 Donald Trump creates the political weather, and voters don’t like it

17:15 Trump blamed the shutdown for the losses, giving Dems more leverage

19:00 Voters blame R’s over D’s for the shutdown by 10 point margin

21:45 We could see more Republican retirements from congress

23:15 Likely the Supreme Court rules against Trump’s tariffs

25:00 Election results could reshape the redistricting fight

26:00 When dust settles, redistricting may not swing advantage to either side

27:30 Cost of living is going to be the defining issue in the midterms

29:15 Democrats mistake with Latinos was appealing to identity, not class

30:00 It wasn’t a good night for Democrats, it was a GREAT night

31:30 Republican candidates will start to distance themselves from Trump

34:15 Democrats now have a reasonable shot at winning the senate

38:00 Rep. Oye Owolewa and George Laws Garcia join the Chuck ToddCast 

40:00 Over 3 million Americans don't have representation 

42:15 The status of Puerto Rico's fight for statehood 

44:30 Public split in Puerto Rico over its status 

46:45 DC can pass local laws governing DC and Puerto Rico 

47:30 Puerto Rico's residents have 58% support for statehood 

49:45 Should DC be holding more referendums on this issue? 

50:45 The importance of lobbying people in other states 

52:15 Muriel Bowser has been boxed in by the administration 

53:30 DC and neighboring states don't want to integrate 

54:30 Should Virgin Islands join the fight for statehood? 

57:30 DC would be solidly Democratic, Puerto Rico is more up in the air 

58:15 Would DC & Puerto Rico have to both get statehood at the same time? 

1:00:00 A new constitutional amendment may need to be passed 

1:01:00 States are only added as duos due to political considerations 

1:02:00 The GOP won't add DC as a state without a Republican counterpart 

1:04:15 Puerto Rico's politics would be a huge question mark if admitted 

1:05:45 How would the four congressional seats in PR split politically? 

1:07:15 Is there a middle ground that would grant rights without statehood? 

1:09:30 Why half measures wouldn't work, Congress could claw things back 

1:11:00 Statehood admission much easier to pass than an amendment 

1:13:30 There is some bipartisan support for statehood 

1:16:00 Could the PR statehood push get a boost from NY and FL? 

1:17:00 DC lost out on huge amounts of Covid money by not being a state 

1:19:30 Puerto Rico receives massively unequal funding relative to states 

1:22:15 Puerto Rico pays more in federal taxes than at least 3 states 

1:24:15 Tax base in DC would be stronger with statehood 

1:25:00 Business are hesitant to operate in DC without statehood status 

1:27:00 Puerto Rico had a huge manufacturing base that has diminished 

1:29:00 Statehood wouldn't harm people living in other states 

1:31:00 States were added in 19th century where English wasn't primary language

1:33:30 Chuck's thoughts on the interview with Rep Oye and George Laws Garcia 

1:34:30 Ask Chuck 

1:35:00 Was Mamdani's political skill the difference vs other progressives who lost? 

1:45:45 Thoughts on Elise Stefanik running for governor of New York? 

1:50:45 How will Biden's presidency be viewed in 30-40 years? 

1:56:30 What would Ronald Reagan think about Trump? 

2:05:00 College football preview

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