Lawfare Podcast: The Trials of the Trump Administration — December 19, 2025

Overview

This episode, hosted by Benjamin Wittes (Editor-in-chief, Lawfare), features senior editors Anna Bauer, Molly Roberts, Eric Columbus, and public service fellow Lauren Voss. The group discusses the latest developments in the prominent legal battles plaguing the Trump administration—including the government’s mishandling of high-profile re-indictments, bizarre grand jury dynamics, constitutional controversies in National Guard deployments, ongoing court showdowns over Trump-era policy, and headline-grabbing building projects. This is the last regular episode of “Lawfare Live” for the year, packed with analysis, speculation, and the group’s signature dry wit.

Key Discussion Points & Insights

1. The Richmond Litigation and the Comey Case

Background: Dan Richmond sought the return of his property, seized and central to the Comey prosecution, under Rule 41(g). Judge Collar Catelli ruled the government violated Richmond’s Fourth Amendment rights and ordered the return and deletion of the data—allowing a copy only to be deposited with the court.

• DOJ’s Unusual Arguments: DOJ challenged the order, arguing it intruded on the executive’s chain of custody and would force them to violate federal records laws—despite the administration’s own casual record-keeping practices.

  • “I just find it so bizarre you’re telling a court that deals with sensitive materials all the time, like, ‘Oh, we need to tell you how to preserve this evidence.’” (Anna Bauer, 06:46)

• DOJ Noncompliance: The government provided a copy to a classified information officer against the court’s order, earning a rebuke from Judge Collar Catelli and a demand for additional briefings.

  • “Judge Collar Catelli is like, wait a second, this is new. You were supposed to make this all about how the court would keep these materials.” (Anna Bauer, 09:37)

• Comey Case Stalled: The podcast speculates whether the Richmond litigation is blocking re-indictment of Jim Comey or whether other factors—statute of limitations or ethics concerns—are responsible.

  • “It's a bit of a mystery at this stage why we’ve had two subsequent efforts to indict Letitia James and none on Jim Comey.” (Benjamin Wittes, 16:48)

2. Grand Jury Roadblocks in the Letitia James Prosecution

Background: Lindsay Halligan initially secured a grand jury indictment against NY AG Letitia James, but two subsequent grand juries have refused to indict, even taking the rare step of publishing the rejected indictment.

• Weaker Indictments and Tactics: The newer indictments are factually “less loose,” yet make the case weaker, focusing on limited evidence (like occupancy, not rents).

  • “Is this a stronger indictment or a weaker indictment? And the answer’s kind of yes... It’s stronger in that it plays less fast and loose with the facts, so it feels a little more legitimate... But it doesn’t have that she got thousands of dollars in rents... which actually makes it read weaker.” (Molly Roberts, 20:15)

• Why Grand Juries Refuse: The team analyzes four possible reasons grand juries are resisting—improved legal accuracy, different grand jurors, heightened media awareness of prosecutorial abuses, and the tainted reputation of these cases.

  • “I think they’ve read the news. These are in Alexandria... It’s odd for the grand jury to present the indictment in open court, and that suggests a level of savviness to me.” (Molly Roberts, 28:35)

• Memorable Moment: The group’s dry consensus—each grand jury attempt gets “worse for her…and for Keller, and that that trajectory is unlikely to be a coincidence” (Wittes, 29:16).

3. National Guard Deployments: D.C. & California Showdowns

A. D.C. National Guard (Judge Jia Cobb & D.C. Circuit)

• Judge Cobb’s Injunction: Ruled against DoD’s authority to deploy the D.C. Guard under certain orders, but the D.C. Circuit swiftly stayed her decision pending appeal.

  • “If you go out this weekend, you will still see them playing chess is the takeaway here.” (Lauren Voss on the visible troops in Dupont Circle, 32:24)

• Statutory Authority Controversy: Arguments hinge on whether 32 U.S.C. § 502(f) authorizes “missions” beyond training and whether presidential authority over the D.C. Guard is limited.

  • “Panel appears to be reading federal mission authority into 502(f) and kind of ignoring all of those other sections…” (Lauren Voss, 36:28)

• Concurrence on D.C. Standing: Judges Rao and Katsas suggest D.C. lacks Article III standing—D.C. is not a sovereign separate from the federal government.

B. California National Guard (Ninth Circuit Turmoil)

• Preliminary Injunction: Judge Breyer enjoined deploying California Guard in LA, handing control back to the state governor. Ninth Circuit panel partially stayed, keeping troops out of LA but halting the return of control to the governor.

  • “The less than 100 California National Guard troops that were in Los Angeles are off the streets. They’ve been pulled out… and are conducting training instead.” (Lauren Voss, 44:12)

4. Judicial Accountability: Wisconsin State Judge Convicted

Case: Wisconsin Judge Hannah Dugan convicted of felony obstruction for assisting a criminal defendant in evading ICE officers at a courthouse.

• Key Testimony: A fellow judge testified, “Judges shouldn't be helping people evade arrest.” (Recapped by Anna Bauer, 53:04)
• Jury Dynamics: Acquittal on the misdemeanor, conviction on the felony—possibly hinging on jury instructions defining knowledge and intent.
• Panel’s Reflection: The hosts debate whether her actions, while factually guilty, are mitigated by context and motive.
  • “Is this a situation where you think she is factually guilty but there’s an ameliorating quality to motive?” (Wittes, 56:48)
  • “I don’t know that I would have believed she’s factually guilty…on the element of corrupt obstruction.” (Eric Columbus, 59:03)

5. Judicial Process and Separation of Powers (Judge Boasberg/Contempt Proceedings)

• Contempt Process Debate: D.C. Circuit (Judges Rao and Walker) questions Judge Boasberg’s authority to investigate and delay criminal contempt referrals.
  • “They both took the view...that Boasberg had crossed a line by proceeding with this contempt proceeding. And then Boasberg turns around and continues to proceed... I think part of what this is, is the D.C. Circuit saying...we told you to cut it out.” (Benjamin Wittes, 68:06)

6. Congressional Oversight of ICE Facilities

• Judge Cobb’s Ruling: Sided with members of Congress seeking access to immigration detention centers without prior notice, based on clear appropriations rider. She held members have standing—deviating from Raines v. Byrd.
  • “The main battle here is whether or not a member of Congress has standing...and Judge Cobb says yes.” (Guest Legal Expert/Eric Columbus, 70:05)

7. Second Amendment Rights & Non-Citizens (Sixth Circuit)

• Upholding the Law: Sixth Circuit upholds federal ban on firearm possession by non-lawful immigrants.
• Concurring Opinion—Judge Thapar: Suggests Second Amendment (and perhaps First and Fourth as well) applies only to “the people”—meaning U.S. citizens, a far-reaching originalist argument.
  • “Judge Thapar as… a strong contender for the next Supreme Court vacancy… Anything they do should be considered an audition… He seems to go even further and says…non-citizens are not part of ‘the people’…” (Guest Legal Expert/Eric Columbus, 77:44)
• Panel Reaction: “That ship sailed a long time ago...” (Wittes, 80:08)

8. Who is the Administrator of DOGE?

• DOGE FOIA Litigation: DC Circuit denies further review, paving the way for discovery into who administrates the elusive Doge office; Amy Gleason expected to be deposed.
  • “Looks like we could actually get some insight into who is the administrator of DOGE at some point after DOGE has ceased to exist.” (Anna Bauer, 87:20)

9. Trump-Era White House Construction Projects

• East Wing/Ballroom: Judge Richard Leon allows below-ground construction for the new White House ballroom to proceed, with pending review of above-ground work and historic preservation legal challenges. The ballroom—now reportedly costing $400M—continues to grow in scale.

• East Potomac Golf Course Debris: Rubble from the demolished East Wing, possibly containing asbestos, has been dumped on a DC golf course. The National Lynx Trust has yet to see test results for hazardous materials.

  • “[There’s] a giant pile of debris on top of the East Potomac Golf Course [that] contains large quantities of asbestos.” (Wittes, 93:13)

• Old Executive Office Building (OEOB) Lawsuit: Legal challenge continues against painting the OEOB white; four downtown brutalist buildings also targeted for demolition—potentially part of a broader “classical DC” agenda.

  • “Trump wants to paint it white. He thinks it’ll look great. Laura Ingraham even asked whether it would look like a big white blob.” (Molly Roberts, 94:01)

10. CFPB, Agency Dismantling, and the Epstein Files

• CFPB’s Fate: D.C. Circuit grants en banc review in the case over dismantling the Consumer Financial Protection Bureau, possibly delaying or reversing its “hollowing out.”

• Epstein Files Released: DOJ partially complies with the law requiring release of Epstein files—so far, mostly photographs, some new, some known, search features lacking. Expect continued scrutiny in coming days.

  • “This is far from the first time Congress has mandated DOJ to meet a deadline… that deadline has not been met.” (Guest Legal Expert/Eric Columbus, 100:43)

Notable Quotes & Timestamps

• “The government…make a number of arguments that, to me, sounded really wild.”
  — Anna Bauer (03:16)

• “Every time they try it, it gets worse for [Halligan], definitely, and for Keller. That trajectory is unlikely to be a coincidence…”
  — Benjamin Wittes (29:16)

• “The Court of Appeals…does also say…defendants are likely to succeed on the appeal because you have D.C. law that allows it. …I think that, keep in mind, this could very well be the kind of thing where we get one order from this three judge panel and then there’s an en banc rehearing…”
  — Lauren Voss (36:28, 68:52)

• “Judges shouldn’t be helping people evade arrest.”
  — Anonymous judge’s testimony (recapped by Anna Bauer, 53:04)

• “I don’t know that I would have believed that she is factually guilty…”
  — Eric Columbus (59:03)

• “I think part of what this is, is the D.C. Circuit saying to a district judge, ‘We told you to cut it out.’”
  — Benjamin Wittes (68:06)

• “Judge Thapar…goes one step even beyond that by analyzing…suggesting those rights do not apply to a legal person unlawfully present and quite possibly might not extend to even people who are lawfully present, but who are not citizens.”
  — Guest Legal Expert/Eric Columbus (79:31)

Timestamps for Key Segments

• Opening/Recap & Rundown – 01:14
• Richmond litigation/Comey case – 03:16–16:48
• Letitia James prosecution/grand juries – 19:24–30:35
• D.C. Guard and Ninth Circuit National Guard litigation – 31:05–46:19
• Wisconsin judge's obstruction conviction – 51:25–61:11
• Judicial contempt proceedings (Judge Boasberg) – 63:41–68:35
• Congressional oversight of ICE facilities – 70:05–74:40
• Sixth Circuit Second Amendment ruling – 75:36–81:17
• DOGE administrator litigation – 84:44–87:42
• White House/East Wing, golf course debris, OEOB lawsuits – 88:28–96:02
• CFPB, agency dismantling – 96:55–99:20
• Epstein files release – 100:04–102:49
• Listener questions – 104:52–107:42
• Closing remarks – 107:42–110:03

Tone & Takeaways

The panel maintains an informed but conversational, occasionally wry tone—often highlighting the surreal or alarming nature of current legal events. The consensus: the Trump administration’s legal tactics frequently push the bounds of both law and governmental norms, with courts and grand juries increasingly resistant to those efforts. There’s recognition of deep constitutional questions at play—on separations of powers, rights of non-citizens—and a bleak amusement at the continual spectacle of executive branch overreach, failed prosecutions, and institutional decay.

For those wanting a thorough but lively account, this episode offers expert context and frank assessment of some of the most consequential (and, at times, strange) legal developments at the end of 2025.