Trump vs. Chicago: Escalation and Political Theatre

As the government shutdown stretches on, Chuck Todd breaks down how both parties are calculating the political costs — and why Democrats may have already achieved what they wanted. With air travel disruptions mounting and healthcare debates pulling in new Republican attention, the public’s patience is wearing thin. Meanwhile, tensions between Trump and Illinois leaders have escalated, raising questions about the politicization of the military and fairness in immigration enforcement.

He also examines Democrats’ deeper strategic struggles heading into 2026 and beyond — from misreading voters’ frustration with cost of living to failing to invest early in registration and outreach. Inside the party, Virginia rallies around Jay Jones, while figures like Elissa Slotkin and Gavin Newsom position for future national influence. But viral missteps, like Katie Porter’s interview fallout, reveal how Democrats are still struggling to master modern media and messaging in an increasingly short-form political world.

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 Introduction

00:30 Government shutdown lingers on, Dems accomplished what they wanted 

01:45 Air travel starting to be impacted by shutdown 

03:00 The healthcare issue has gotten the attention of Republicans 

04:00 General public only cares about issues that directly impact them 

05:00 Either party could end the shutdown now 

07:15 Showdown between Trump & leaders in Chicago escalates 

08:15 Using Texas national guard in Illinois is a bridge too far 

09:15 Too many leaders on both sides are way too online 

10:30 ICE found by judge to be making warrantless arrests 

12:45 Trump and Stephen Miller overplaying threat to the public 

13:30 Public doesn't support deployments, wants apolitical military 

14:45 Majority of voters think deportation process hasn't been fair 

16:15 Politics getting personal between Trump & Illinois leaders 

18:15 There are political risks for both sides 

19:15 DNC believes they didn't spend early & enough to engage voters in 24' 

21:45 Democrats takeaways are wrong. Biden was the biggest issue 

23:00 Biden team misread the room, voters were upset at cost of living 

24:15 DNC has put enough effort into voter registration 

25:00 Appears party leaders in VA will rally around Jay Jones 

26:45 Democrats willing to engage in GOP style "whataboutism" 

28:00 There's still a vast chunk of America that cares about ethics 

29:30 Elisa Slotkin headlining dinner in NH, eyeing run for president? 

30:30 Looking like Gavin Newsom will win redistricting referendum 

32:30 If California votes yes, it looks like R's will only pick up 3-4 seats in 26' 

33:15 Katie Porter crashes out in viral interview clip, both parties pile on 

35:00 Has Porter spent too much time in friendly interview spaces? 

36:30 Porter's response to losing senate primary to Schiff was revealing

38:00 Former Bernie strategist says Dems struggling with short form video

41:00 Ask Chuck 

41:15 Should we offer a tax credit for voting to incentivize participation? 

45:15 Thoughts on an "American Unity" platform? What would you include? 

52:00 Trump modeling terrible behavior & character for young people? 

59:45 Military pay during government shutdown? 

1:02:15 College football preview

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