The Lawfare Podcast: The Trials of the Trump Administration

Episode Date: December 12, 2025
Released: December 15, 2025
Host: Benjamin Wittes (joined by Anna Bauer, Eric Columbus, Molly Roberts, Lauren Voss, and others)
Main Theme:
A comprehensive, topical roundup of the latest federal court developments tied to the Trump administration—including ongoing Trump-related litigation, dramatic courtroom moments, executive branch legal shakeups, and the evolving challenges around national security, immigration, and the scope of executive power.

Episode Overview

The episode offers a dense, rapid-fire review of several high-stakes legal matters involving the Trump administration and related legal actors, with a particular focus on:

• Highly charged immigration and contempt proceedings
• The ongoing chaos of leadership within US Attorneys’ offices
• National Guard deployment and "Insurrection Act" litigation
• A Supreme Court challenge to limits on presidential removal of agency officials
• The repercussions for witnesses caught in legal crossfire

The panel maintains Lawfare’s signature mix of legal precision and dry wit, with ample attention to shifting legal standards, courtroom theatrics, and moments where the government appears at odds with itself or the courts.

Key Discussion Points & Insights

1. Trump-Related Immigration and Contempt Proceedings

a. The JGG/Alien Enemies Act Case (Host: Anna Bauer)

• [02:44 – 08:11]: Judge Boasberg in D.C. is moving forward with contempt proceedings regarding a government-ordered return of planes to the US—a security/immigration saga that saw government witnesses firm-ordered to testify despite intense DOJ resistance and claims of privilege.
  • Quote:
    “He wants to move forward with this and denied the motion for reconsideration to put a stop to this testimony.” — Anna Bauer [04:56]
  • The government sought emergency relief (writ of mandamus) from the D.C. Circuit, focusing on privilege and whether the order was ambiguous enough to preclude contempt.

Significance: If allowed, such testimony would mark an extraordinary moment of judicial consequence for government lawyers and officials.

• Notable moment:
  “It’s possible this testimony could go forward on Monday and Tuesday, which will be quite extraordinary. I plan to be there if it does.” — Anna Bauer [06:57]

b. The Kilmar Abrego Garcia Civil and Criminal Cases

• [09:28 – 26:00]: Deep dive into the legal odyssey of Abrego Garcia—a man whose wrongful deportation led to his temporary freedom, protracted court battles, and continual government maneuvering.
  • Judge Sinis ordered his release after finding there was never a proper order of removal and highlighted repeated bad-faith conduct by the government.
  • Quote:
    “She quite literally says that the government affirmatively misled the court…” — Anna Bauer [17:27]
  • The government rapidly tried to re-deport, leading to a court-ordered TRO and with the judge signaling she is “just to the end of her rope.”

Memorable background:
“This is the first time this man has been really at home with his family after many months of being wrongfully deported to El Salvador.” — Anna Bauer [21:27]

• In parallel, the criminal case in Tennessee is mired in sealed discovery disputes and tribulations over claims of vindictive/selective prosecution, with several scheduled hearings canceled and crucial evidence potentially withheld under claims of privilege.

2. Other Key Immigration-Related Litigation

a. Faustino Pablo Pablo Case (Eric Columbus)

• [26:29 – 33:09]: Another egregious scenario—Pablo Pablo, a Guatemalan with a judicial order barring his removal to Guatemala (due to risk of torture), was detained and deported anyway, triggering emergency litigation and a court-ordered return.
  • Judge plainly “sliced through the Gordian knot of jurisdiction.”
  • The panel underlined both the frequency of such cases and the government’s habit of offering shifting, inconsistent excuses.

b. Rameza Osterk Case

• [33:09 – 34:27]: The student’s visa work status was abruptly revoked after speech against Israel’s Gaza actions, but a Massachusetts judge found the government’s conduct “arbitrary and capricious,” forcing her reinstatement.

Anna Bauer notes:
“The judge…found her termination in the database was likely arbitrary and capricious because the government had been offering shifting explanations…” — Eric Columbus [33:09]

3. National Guard and “Insurrection Act” Cases

a. Judge Breyer & California National Guard Litigation (Molly Roberts)

• [34:07 – 45:28]: Ongoing struggle over the President’s power to federalize state troops.
  • Judge Breyer granted a preliminary injunction returning control of the California National Guard to the governor, sharply criticizing the lack of evidence for continued federalization.
  • Quote:
    “He actually says that the government’s assertion that there’s an inability to execute the law that remains in California is not only unsupported, but it actually borders on a misrepresentation.” — Molly Roberts [39:06]

Important insight: Frequent, short federalization orders may evade judicial review; the government’s logic risks turning state guard troops into a “national police force.”

b. Ninth Circuit, Oregon, and En Banc Adventures (Molly Roberts)

• [51:14 – 59:07]: Judge Jay Bybee’s statement—worthy for its historical sweep and constitutional debate—claims the Constitution’s “domestic violence” clause limits presidential deployment of the militia absent state consent, except in cases where a state is itself the lawbreaker (e.g., opposing desegregation).

  • Quote:
    “The domestic violence clause provides no basis for objection when the states themselves are the source of or have acquiesced in the unrest.” — Molly Roberts, quoting Bybee [57:03]

Takeaway: Raises specter of future chaos in the President/state relationship over federal deployments.

4. Leadership Chaos Among US Attorneys

a. Richmond’s Motion & The Issue of Unlawful Appointments (Anna Bauer, Molly Roberts)

• [60:29 – 71:05]:
  • Dan Richmond (former witness in the Comey matter) is trying to secure the return of his electronic property (seized and re-searched years later as DOJ pursues new Trump-era cases).
  • The government’s slow-walking and now-firewalled TRO raises broader questions about ongoing prosecutions—including whether improperly appointed U.S. attorneys can press cases.
    • Quote:
      “They’re claiming that this has hamstringed the Comey prosecution and their efforts to, you know, potentially pursue a further indictment.” — Anna Bauer [68:27]

b. Fall-Out from Invalid US Attorney Appointments

• [72:56 – 81:00]: A tangled account of three acting or interim US attorneys stepping down after the 3rd Circuit ruled them unlawfully appointed. Their replacements have tenuous authority, and the government’s refusal to fully comply (still listing invalid appointees on filings) is drawing the ire of judges and line prosecutors alike.
  • Quote:
    “If you were another judge… you might be a little miffed if I started seeing Lindsey Halligan’s names on… indictments… because the Eastern District of Virginia did rule she’s not validly the U.S. Attorney at all.” — Neal Katyal [80:00]
  • Even the Office of Legal Counsel is providing “five different internal guidance emails” on how to sign court filings.

Details:
– Alina Habba, after being ousted in New Jersey, is made a “special attorney” for the Attorney General—a newly invented role.
– Line prosecutors and the DOJ are left navigating a complex, risk-laden landscape with every outgoing appointee.

5. Supreme Court: Humphrey’s Executor on the Chopping Block (Eric Columbus)

• [88:52 – 95:19]: The Supreme Court is poised to overturn Humphrey’s Executor, paving the way for presidents to fire independent agency heads at will.

  • Quote:
    “There wasn’t much suspense going into oral argument. The only real question was how broad the opinion will be…” — Eric Columbus [90:11]

This could render the nonpartisan civil service a relic—and, ironically, may only “carve out” the Federal Reserve for unique protection.

6. FBI Agents Fired for Non-Lethal Response to Protests

• [95:56 – 98:25]: Twelve FBI agents, fired after kneeling to de-escalate during the 2020 D.C. protests, are suing for violation of First and Fifth Amendment rights. The firings came after intervention by new leadership (Kash Patel) and could presage future, more politicized purges.

Notable Quotes & Memorable Moments

• “It’s all starting to congeal into, like, a Frankenstein monster.” — Molly Roberts on interlocking National Guard cases [33:50]
• “She is pointing to and developing this record of all the instances here that the government has just acted with a true…disregard for the court’s authority.” — Anna Bauer [17:27]
• “The government keeps extending California National Guard. We’re talking about 300 troops right now… The President’s creating a national police force by state troops.” — Molly Roberts [35:21]
• “I think pissed off describes it a little better. She’s not the only judge…who has felt that way.” — Benjamin Wittes on judges’ reactions to invalid U.S. attorney signatures [81:00]
• “The only real question was how broad the opinion will be that overturns Humphrey’s Executor.” — Eric Columbus [90:11]
• “So I don’t know, maybe they’ll try [to indict Letitia James] again. But each of these, each time they try, it’s fuel for selective and or vindictive prosecution motion.” — Benjamin Wittes [87:35]

Important Timestamps

• 02:44 – Start of deep-dive into Trump-related contempt and immigration litigation
• 08:11 – Summary and developments in JGG and Abrego Garcia cases
• 26:29 – Eric Columbus introduces similar case: Faustino Pablo Pablo
• 33:09 – Rameza Osterk’s legal victory and government’s arbitrary actions
• 34:07 – Discussion on National Guard litigation, Judge Breyer’s ruling
• 39:06 – “Borders on a misrepresentation”—Breyer’s strong language
• 51:14 – Ninth Circuit/Bybee’s historical constitutional argument
• 60:29 – Richmond’s 4th Amendment/TRO saga and implications for Comey prosecution
• 72:56 – Alina Habba’s fall, new DOJ leadership workarounds
• 80:00 – Judicial backlash against Halligan’s continued signing of filings
• 88:52 – Upcoming Supreme Court gutting of Humphrey’s Executor
• 95:56 – Lawsuit by FBI agents / Article II firings
• 101:07 – Audience Q&A: Grand jurors, Halligan on filings, contempt powers

Style & Tone

The conversation is expert-level, serious, and sometimes sardonic, carrying Lawfare’s signature blend of legal rigor, procedural nerdery, and gallows humor while dissecting weighty constitutional questions, bureaucratic drama, and the granular details of national security litigation.

For Listeners Who Haven’t Tuned In

This episode is essential listening for anyone trying to keep up with the complex and fast-evolving landscape of legal challenges surrounding the Trump administration, the rule of law under sustained stress, and the constitutional architecture of executive power. The panel’s breadth of coverage, attention to procedural as well as substantive quirks, and willingness to debate the import of even arcane legal maneuvers makes this an invaluable guide to the headlines behind the headlines.

Endnotes

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