Would You Work With Donald Trump?

As the country hurtles toward the 2026 midterms, Chuck Todd breaks down why winning in this moment may be more about margins than movements—and why messaging is about to get brutally hard. With a fragmented, exhausted electorate and a president acting emboldened despite weak political standing, Democrats face a defining choice: run as resistance to Donald Trump or position themselves as problem-solvers ready to turn the page. History suggests forward-looking messages work best, especially with independents who vote in self-interest and are tired of constant political warfare, even as Trump continues to dominate GOP primaries and sideline Congress.

The conversation also looks at why Republicans’ razor-thin majority leaves them unable to govern, how Trump’s grip on the party could backfire in a general election, and why Democrats are increasingly optimistic about putting the Senate in play—with strong recruiting wins and favorable midterm math. New polling on the Renee Good shooting and ICE shows Trump-aligned tactics playing poorly outside the MAGA base, particularly with independents and women, underscoring just how volatile—and opportunity-rich—the political landscape could be heading into 2026.

Then, Jon Slavet, a tech entrepreneur and Republican candidate for California governor, joins the Chuck ToddCast to discuss why he's entering one of the nation's most challenging political races. Slavet argues that while national politics dominates headlines, state and local governance has far more impact on people's daily lives—yet California's local politics receives inadequate attention despite intense interest from outsiders. He advocates for radical transparency in government, criticizing the use of NDAs in taxpayer-funded projects and calling out the influence of union spending. Addressing his controversial pursuit of Trump's endorsement despite never voting for him, Slavet positions himself as someone who sees Trump as an effective disrupter but not a builder, and he aligns with the administration on housing policy, particularly prioritizing temporary shelter over California's $1 million-per-unit permanent housing approach.

Running as a Republican in deep-blue California, Slavet believes the state's pleasant weather has masked serious problems affecting middle and lower-income residents while the wealthy thrive. He proposes declaring an "affordability emergency" on day one, scrapping the high-speed rail project, and using AI to root out the billions lost to waste and fraud in California's healthcare system. Slavet defends his decision to run as a Republican rather than an independent, arguing that party identification remains essential for effectiveness despite his moderate positions on social issues like same-sex marriage and abortion. He contends that polls show half of Californians would support the "right kind" of Republican, and he's betting his business success and willingness to challenge both parties' orthodoxies will resonate with voters frustrated by the state's affordability crisis and regulatory burdens on small businesses.

Finally, Chuck gives his ToddCast Top 5 championship winning Miami Hurricanes football teams & 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

03:45 Messaging will be incredibly difficult in this political environment

04:15 If Dems only win house, it will be considered a partial rebuke of Trump

05:15 Trump is weak politically but acting like he has a ton of capital

06:00 Trump feels emboldened to play “Risk” with the world

06:45 Administration will likely back off investigation into Jay Powell

08:00 Talking to a fragmented and exhausted electorate will be tough

09:15 Elections are always won on the margins, not just by the base

10:30 Analysts project their preferences onto the electorate & swing voters

11:30 What is the most effective way to win elections in 2026?

12:30 Democrats will have to balance accountability vs. forward facing

14:15 “Would you work with Donald Trump?” a defining question for Dems

16:15 Dems have to decide whether they are resistance or problem solvers

18:00 History suggests forward looking messages are more effective

19:00 Most voters vote in self-interest, not for the greater good

19:45 After 10 years of Trump, the public is exhausted by politics

20:45 "Turn the page” messaging may appeal to independents

22:30 GOP primaries will be all about Trump, but cause problem in general

24:00 Trump can break ideological rules other Republicans can’t

25:00 GOP majority is so narrow they can’t really govern

25:45 Trump is increasingly uninterested in working with congress

27:15 “Vote GOP to stop impeachment” isn’t enough to woo swing voters

28:00 Growing number of R’s uncomfortable with Trump’s actions

28:45 Dems got a huge recruiting victory in Alaska with Mary Peltola

30:30 Peltola puts Alaska in play, making senate control more possible

31:45 Sherrod Brown has won in midterm years in Ohio

33:15 Democrats much further along in putting senate in play

34:30 Historically the party out of power picks up 4 seats, Dems need 4

36:30 Majority of Americans say Renee Good shooting not justified

37:15 Majority of independents & women say it was unjustified

38:15 82% of respondents were aware of the Renee Good shooting

39:15 57% disapprove of ICE

40:30 ICE + Minneapolis not playing well outside MAGA base

41:30 Kristi Noem is an easy scapegoat, could get dumped

49:00 Jon Slavet joins the Chuck ToddCast

50:45 Why enter politics and run for governor of California?

52:30 It’s fraught & dangerous to run for office in this political climate

53:15 National politics get attention, state & local more impactful

54:45 Serious lack of attention to local politics in California

56:00 There’s a ton of interest in California from people outside it

57:15 NDA’s should not be allowed in taxpayer funded projects

58:45 Major government discussions need more transparency in CA

59:15 Unions raise $1B in CA and spend $300 on political donations

1:00:00 Why seek Trump’s endorsement after not voting for him 3x?

1:01:15 Trump is good as a disrupter but not as a builder

1:02:00 Where do you agree with Trump on policy?

1:02:30 HUD’s new policy prioritizes temporary, not permanent housing

1:03:30 Permanent housing for homeless costs $1M per unit in CA

1:05:00 The priority should be getting homeless into temp housing ASAP

1:06:00 Could you have been as successful in a state other than CA?

1:07:15 California’s great weather masks many of its problems

1:08:30 Tech doesn’t suffer from regulatory issues like other industries

1:09:15 Middle & lower income Californians are suffering, rich doing great

1:11:30 Half of California’s work for small businesses that are overtaxed

1:14:00 Where will you find the money to fund your proposals?

1:14:30 California should scrap the high speed rail to nowhere

1:15:30 Jon would declare an affordability emergency on day 1

1:17:00 California’s healthcare costs $160B, Medicare fraud is 10–15%

1:18:30 AI can be used to root out waste, fraud and abuse in state budget

1:20:00 Californians pay huge taxes on fuel & energy

1:21:30 Why run as a Republican and not an independent?

1:23:00 We should be way beyond the same-sex marriage debate

1:24:00 Abortion is settled law in California

1:25:30 Why Jon was against Prop 50 in California

1:26:30 Gerrymandering is terrible for democracy

1:28:15 Running as independent isn’t effective, people identify w/ parties

1:29:45 The race will be a Trump referendum, how does a Republican win?

1:31:30 Polls show half of CA will vote for the “right kind” of Republican

1:32:45 CA has had plenty of billionaires run & fail to win elections

1:35:00 Has Silicon Valley been regulated enough?

1:36:15 AI boom has been critical for San Francisco’s comeback

1:37:45 Would you ban social media for kids under 16?

1:39:30 Would you ban phones in schools?

1:40:15 How do you convince CA voters the wealth tax is a bad idea?

1:42:15 How would you work in a bipartisan manner with Dem state house?

1:45:00 Chuck’s thoughts on interview with Jon Slavet

1:45:30 There’s a lack of star power in CA governor race

1:46:15 ToddCast Top 5 Miami Hurricanes football teams if ’25 team wins title

1:49:00 #1 2001

1:51:00 #2 1987

1:52:30 #3 1993

1:54:00 #4 1983

1:55:00 #5 2025

1:58:30 Ask Chuck

1:58:45 In today’s climate would it benefit a candidate to avoid negative ads?

2:02:15 Are traditional Republicans missing a chance to push back on Trump?

2:09:15 Did Biden cater too much to the far left & hurt appeal with swing voters?

2:11:15 How is public media likely to continue on?

2:13:45 Can Democrats make Mississippi competitive?

2:19:30 Are we still capable of recognizing normalization of democratic collapse?

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