Trump’s Lawlessness + Showdown With SCOTUS Looming?

Chuck Todd is joined by Benjamin Wittes, editor-in-chief of Lawfare, to break down the widespread legal violations committed by the Trump administration during Donald Trump’s first three months in office.

Chuck opens the episode by underscoring the gravity of the moment and why Trump appears to show little respect for the law or the authority of the courts.

Ben Wittes then joins the conversation to discuss the constitutional amendments the administration may have violated, whether Trump is defying Supreme Court rulings, and what a potential legal showdown over his immigration policies could look like.

They examine the administration’s targeting of law firms and universities, where institutional pressure could serve as a check on executive overreach, and whether lawsuits filed by state attorneys general stand a chance in court.

Finally, they unpack Trump’s use of executive orders against his critics, why the U.S. is losing its reputation as a global “beacon of freedom,” and Ben shares one reason he still holds onto a sense of optimism.

0:00 First 90 days of the Trump administration has been tumultuous 

1:45 Congress is sitting on its hands

2:45 The administration is slowing down routine investigations 

4:00 This is a dangerous moment for the country

5:30 Trump is “flooding the zone”

8:15 There are legal ways to handle deportations but Trump isn’t interested

9:30 They’ve violated amendments four through nine

11:30 Trump left Biden a legal quagmire over the border, but Biden didn’t handle it well

12:30 Prices will rise in the next 60-90 days 

14:00 Incompetence has defined Trump’s administration thus far

15:00 Administration is trending toward monarchy 

16:45 Lindsey Graham has gone radio silent

18:55 Benjamin Wittes joins the show! 

21:10 Trump is violating multiple constitutional amendments 

23:30 Is Trump violating the Supreme Court ruling? 

25:55 Did the Supreme Court water down their ruling? 

27:05 All 9 justices agreed on the premise 

28:05 What would satisfy the court's order to "facilitate" the return of Abrego Garcia? 

29:40 If Trump asked for the prisoner back, Bukele wouldn't say no 

30:45 The White House is brazenly violating court orders 

32:10 The administration is extorting law firms 

36:45 How will Harvard's decision to fight back affect them? 

38:35 Is the administration going out of their way to pick fights? 

39:55 They're creating criminal impunity for allies 

40:45 Administration is using civil litigation to target enemies 

41:55 The government will pay more in damages than money saved by DOGE

45:00 John Roberts is issuing rulings meant to avoid confrontation with Trump 

46:25 SCOTUS justices are aware Trump is flaunting their ruling 

48:45 Trump is putting tremendous stress on his own party 

49:25 Are Trump's actions uniting SCOTUS against him? 

52:25 What to make of the three liberal justices putting out a press release? 

54:55 How alarmed are the six conservative justices? 

56:05 Expectations for California's tariff lawsuit? 

58:55 The president has civil immunity from defamation lawsuits 

1:01:15 Targeting Krebs and Taylor are two of the most egregious acts so far 

1:05:25 Trump 2.0 is an entirely different proposition 

1:06:55 What authoritarian model does Trump most emulate? 

1:07:55 Ben projected "Trump and Vance betrayed the country" on the Washington monument

1:10:55 The beacon of freedom has been turned off

1:12:25 Ben's hammock studio 

1:14:15 Administration is targeting people the public doesn't care much about 

1:16:05 The goal is to stop it from getting worse

1:18:03 Showdown with SCOTUS looming?

1:19:30 Chuck’s Nats rant - Fix the bullpen!

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