Chuck Todd opens with a critical analysis of President Trump's approach to governance, suggesting that while his Middle East trip may yield positive results, his administration is missing crucial opportunities for bipartisan cooperation. He argues that Trump's executive order on prescription drugs lacks substance without legislative backing and that the president should "get caught trying" bipartisanship on issues where common ground exists. He also explores Putin's refusal of peace talks as a potential humiliation for Trump, and examines what recent political developments like the Omaha mayoral race might signal about Democratic prospects in upcoming elections.

Then, he’s joined by Congressman Ro Khanna, who delivers a candid assessment of the Democratic party's leadership crisis and brand damage. Khanna argues that Chuck Schumer has squandered his leadership position and addresses concerns about deportations in rural communities. The conversation delves into the economic realities facing the Midwest, and calls for Democrats to work more closely with business leaders.

Khanna argues that deplatforming Trump after January 6th was "a huge mistake" and discusses the rightward shift among tech leaders. They conclude with Khanna's perspectives on America's global retreat, the timeline for presidential campaigns, and Gen Z's trust issues with politics.

The episode wraps with "Ask Chuck," where Todd addresses questions about media coverage of Trump, potential Republican party fractures, and Chuck gives his thoughts on Pete Rose's posthumous Hall of Fame eligibility.

Timeline:

00:00 Introduction

01:45 Trump’s middle east trip may net some positive results

02:30 Trump won’t work with Democrats on issues they agree on

04:15 Bipartisanship has become toxic

06:30 Trump’s executive order on prescription drugs is meaningless without legislation

07:45 Congress has been useless

08:30 Trump should “get caught trying” bipartisanship

10:00 There are multiple issues where Trump could make bipartisan deals

12:15 Trump made some great points in his middle east speech

13:45 Trump has been pragmatic with his middle east policy

16:30 Trump can’t pick and choose who to be pragmatic with

18:00 The ball is in Trump’s court after Putin turned down peace talks

19:15 Putin is humiliating Trump… will he sit back and take it?

19:50 Does the Omaha mayoral race show a blue wave building?

21:00 Pete Buttigieg admits Joe Biden is political baggage in Iowa town hall

23:30 Chuck Schumer punting on the Biden question was cowardly

25:30 Donald Trump is unpopular and the Democratic brand is still worse

26:15 Ro Khanna joins the Chuck Toddcast!

27:45 Who is the leader of the Democratic party?

28:45 Chuck Schumer has squandered his leadership position

31:30 Rural communities are highly concerned about deportations

32:15 Is Hakeem Jeffries stuck in Nancy Pelosi's shadow?

34:00 How damaged is the Democratic brand and how to fix it?

37:15 Do midwestern voters want to work multigenerational factory jobs?

40:30 NAFTA benefitted the south and hurt the midwest

43:15 Republicans have become the big government party

45:45 Democrats need to work with business leaders

46:45 What caused the rightward shift of the tech leaders?

48:30 Deplatforming Trump was a huge mistake

50:30 Should Kamala Harris be the next governor of California?

53:30 What characteristics will voters be looking for in 2028

55:15 Will Democratic voters want a "celebrity" president?

58:25 What's the lesson learned from Biden's communications failure?

1:00:15 How do Democrats win over independent voters?

1:03:00 One issue he'd work with Trump on?

1:03:45 Will he debate JD Vance?

1:05:45 America's retreat is making the world more dangerous

1:07:15 Rubio needs to step up and assert America globally

1:10:00 It will take a generation to repair America's reputation

1:10:45 When is it appropriate to begin a run for president?

1:12:15 Kamala Harris and her team were too cautious in 24

1:13:45 Gen Z has trust issues with politics

1:15:45 Chuck’s thoughts on interview with Ro Khanna

1:16:15 Ask Chuck

1:16:55 Why are reporters not more combative with Trump?

1:19:05 If the Republican party fractures, who would be in the traditional wing?

1:21:45 Pete Rose finally eligible for Hall of Fame posthumously

(Timestamps vary based on advertisements)