Ask Chuck: What If Trump Won Re‑election in 2020?

On this episode of the Chuck ToddCast, Chuck unpacks the latest government shutdown and the political brinkmanship that created it. He explores how shutdowns—once unthinkable—have become a partisan weapon, wasting money while allowing leaders like Donald Trump to punish opponents and play to their base. With Democrats at risk of shouldering equal or greater blame, Chuck asks whether the public is even paying attention, and what role figures like Russ Vought could play in reshaping government permanently. Beyond the shutdown, the conversation turns to the bigger picture: why voters never saw Trump as an aberration, why 2020 wasn’t a full repudiation of 2016, and what Democrats must do to win back Trump voters in 2028. From Harris’s struggle to differentiate herself from Biden to Clinton’s careful dance with Reagan’s legacy, Chuck argues that Democrats may need to admit Trump identified real problems—even as his solutions and behavior, especially with military leaders, remain deeply troubling.

Finally, Chuck presents his ToddCast Top 5 senate races most likely to flip parties, answers listeners’ questions in the “Ask Chuck” segment, and recaps a frustrating night at the Cowboys/Packers game. 

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Introduction - Government begins shutting down

01:15 Congress created shutdown conditions for political leverage

02:00 Could shutdown trigger the end of the senate filibuster rule?

02:45 Democrats have always messaged that shutdowns are bad

04:30 Democrats could shoulder equal or more blame for shutdown

06:30 Shutdowns are a massive waste of money

07:30 Trump seems excited for shutdown to punish opponents

09:15 Terrible trend of politicians only governing for their base 

11:15 Independents are pretty sour on Trump’s presidency

13:00 Russ Vought at OMB could use shutdown to reorient gov’t permanently

14:30 Big danger for Democrats is whether the public is paying attention

15:30 Chuck Schumer is “Mitch McConnell” level unpopular

18:45 If Dems want to win in 28 they’ll have to win over some Trump voters

20:15 Democrats thought Trump was an aberration, voters didn’t

21:15 2020 wasn’t a repudiation of why Trump was elected in 2016

24:00 Voters don’t want status quo, which is why they elected Trump twice

26:15 Harris needed to prove she was different from Biden and didn’t

27:45 For Clinton to win, he couldn’t repudiate everything Reagan did

30:00 Trump’s behavior in front of military leaders was outrageous

31:30 The military leaders handled the situation exactly as they should

32:30 Hegseth lectured leaders of far higher rank than he earned in military

33:45 Democrats will have to admit that Trump correctly identified problems

34:45 Voters picked “political division” as the 2nd biggest problem after economy

37:30 ToddCast Top 5 Senate races most likely to flip parties 

38:00 #1 North Carolina 

39:45 #2 Georgia 

41:45 #3 Michigan 

43:30 #4 Maine 

45:30 #5 New Hampshire 

51:00 Honorable mentions 

51:30 Ask Chuck 

51:45 Why is the lie that shutdown is over money for illegal immigrants pervasive? 

54:45 Democrats feeling disheartened after talking to Trump supporters? 

58:45 Would the country be better off if Trump was reelected in 2020? 

1:03:00 Will Des Moines superintendent arrest derail Iowa senate campaign? 

1:04:45 Chuck's experience at Cowboys/Packers game in Dallas 

1:10:00 It was a great weekend of college football

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