Trump's Redistricting Push and 2026 Strategy

Chief Washington correspondent for Puck News, Leigh Ann Caldwell joins the Chuck ToddCast to unpack how Washington looks different when covered from outside the constraints of legacy media—and why independent journalism may be better suited to capture the dysfunction of Trump’s second term. Caldwell reflects on the groupthink and reaction-driven coverage that defined Trump’s first presidency, the erosion of Congress’s authority in Trump 2.0, and the deep personal animus now defining relationships on Capitol Hill. Together, she and Chuck examine how social media has shaped a younger generation of staffers, why Speaker Mike Johnson may be remembered as one of the weakest in history, and how Congress has willingly made itself irrelevant in the face of executive power.

The conversation also digs into healthcare politics, looming shutdown risks, and why Republicans remain unable to act without Trump’s approval—even as he digs in against ACA subsidies out of lingering grievance toward Obama. Caldwell and Todd explore the brewing chaos inside the GOP, from mass retirements and redistricting fights to the staggering cost of House races and the nonstop fundraising grind. The episode closes with a candid assessment of party leadership heading into 2026, why a third Trump impeachment would be a mistake, and why covering Congress—rather than the White House—may now offer the clearest window into where American politics is headed.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Leigh Ann Caldwell joins the Chuck ToddCast

01:30 Covering politics as independent media vs legacy media

04:45 There was little ability for original thought doing network news

05:45 Legacy media gets stuck in groupthink

07:30 People blame the Gingrich years for our current political dysfunction

09:00 Covering Trump’s 1st term was asking for reactions to Trump

09:30 Congress has handed away their authority in Trump 2.0

10:15 The personal animus between the two parties is very real

11:30 Young staffers had their politics formed by social media

13:30 Mike Johnson will go down as one of the weakest speakers ever

14:30 Johnson has willingly made congress irrelevant

16:15 Are we underplaying the chances of a January shutdown?

17:30 With premiums set to rise, why couldn’t Dems corner the GOP?

18:15 Dems know healthcare is good politics for them

19:15 Trump is digging in rather than caving on ACA subsidies

21:00 Trump doesn’t want to prop up the ACA because Obama passed it

22:00 Lots of Republicans have “Obama Derangement Syndrome”

23:30 The framework of the ACA came from the Heritage Foundation

24:00 Trump comes close to advocating for single payer healthcare

26:15 Republicans can’t do anything on healthcare without Trump

27:15 Trump is done with congress, thinks he can do everything via EO

29:15 Trump lied and claimed military bonuses came from tariff revenue

30:15 If SCOTUS takes tariff power from Trump, will he go to congress?

31:15 Congress unlikely to hand tariff authority to Trump

32:15 Republican bracing for another 20 retirement announcements

33:45 Texas & California members are mad about redistricting

35:30 House races will likely cost $60 million in 2026

37:00 Members of congress spend 50% of their time fundraising

39:30 Democrats would be stupid to try to impeach Trump a third time

41:00 Which congressional leaders will still be in place in 2027?

42:30 Johnson won’t be speaker in a new congress

43:30 Jim Jordan is the quiet favorite to be the house GOP leader

45:00 It’d be shocking if Chuck Schumer ran again

46:30 DSCC botched their oppo release on Graham Platner

48:45 There are doubts about Jeffries, but unlikely to be challenged

50:30 Schumer & Jeffries botched the NYC mayors race

52:15 Does John Thune have support in the senate?

55:00 Covering the hill is a better beat than the White House

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