The Lawfare Podcast: "The Trials of the Trump Administration"

Episode Date: March 9, 2026
Host: Benjamin Wittes
Panelists: Alan Rosenstein, Molly Roberts, Roger Parloff, Troy Edwards
Main Theme:
A comprehensive, in-depth roundtable covering current legal controversies and litigation arising from the Trump Administration’s actions across tech regulation, national security, criminal and bar proceedings, immigration policy, and judicial reactions—all with expert commentary, explanation of mechanics, and some darkly comedic asides.

Episode Overview

This Lawfare Live panel—hosted by Lawfare editor-in-chief Benjamin Wittes and three senior editors, with public service fellow Troy Edwards—delved into a packed agenda of headline legal cases and developments under the Trump administration. The group discussed ongoing lawsuits involving TikTok’s divestiture, Department of Defense actions against AI company Anthropic, controversial prosecutions (including the Don Lemon investigation), baffling DOJ moves in major appellate cases, bar complaints against federal attorneys, evolving press restrictions, a flurry of immigration-related court orders, and rising judicial frustration encapsulated in their inaugural “Cri de Cœur” roundup.

Key Discussions & Insights

1. TikTok Litigation Returns

[05:45–13:09]

• Background: Despite previous assumptions of resolution, TikTok’s divestiture from its Chinese parent ByteDance has landed back in court.
• New Lawsuit: Tony Tan, a Google shareholder backed by the Public Integrity Project, argues the new ownership structure doesn’t meet statutory requirements under the "Protecting Americans from Foreign Adversary Controlled Applications Act" (HAFACA).
• Legal Issue: The operational licensing of TikTok’s algorithm to the “new” American company raises questions of substantial foreign control.
• Key hurdles:
  • Standing: Can a Google shareholder claim specific harm? Alan Rosenstein:

    “The government will likely argue that is not sufficient standing…there are many investors in Google…this is not the sort of particularized injury….” [11:09]

  • Redressability: Is the plaintiff’s alleged injury actually fixable by a win in court?
• Outlook: Uncertain. If it survives dismissal, discovery could be “real fun." [13:09]

2. Anthropic vs. Department of Defense

[13:09–22:08]

• Current Status: DoD slapped an AI company (Anthropic) with a “supply chain risk” designation, initially threatening to bar all defense contractors from any dealings—even basic cloud services.

• Designation Scope Shift:

  • Original threat: An existential business threat.
  • Now: Burdensome, but “no longer an existential threat.”
  • Alan Rosenstein:

    “It's still a large threat…because it reflects the animus that the administration has to Anthropic. …But…the designation is likely to struggle in court.” [22:02]

• Room for Climbdown:

  • “Ideally they could come to some agreement where Anthropic gets to claim…its red lines are being respected, DoD gets to claim it’s fundamentally in control and everyone kisses and makes up.” [19:12]

• AI Speaks: Ben asks Claude (the AI assistant) for its take, which is surprisingly measured and references Lawfare’s own analysis. [20:02–22:08]

  “The question of whether an AI company should be able to set limits on how its models are used in warfare is genuinely important and not easy…”

3. Prosecution News: Don Lemon Case & Odd DOJ Moves

[23:10–32:06]

• Don Lemon’s Case:
  • 30 more defendants added, including overseas arrests under unusual circumstances and debate about government overreaching in executing arrest warrants.
  • Troy Edwards:

    “It could potentially rub the judges the wrong way…they’ve now put a defendant through that process...” [26:49]

• DOJ’s Appellate Head-Fake:
  • Government moved to dismiss its own appeal in law firm security clearance cases, then abruptly reversed course following leaks and pressure:
  • Roger Parloff: “I’ve not seen that, Ben.” [27:56]
  • “Some say it was Trump, some say it was Stephen Miller…” [29:33]
  • D.C. Circuit will now take up both the law firm and the Zaid security clearance cases together.

4. Fulton County: Enter the Mediator

[32:24–35:39]

• Special master/mediator Harold Melton (ex-Chief Justice, Supreme Court of Georgia) appointed to broker a resolution re: handling of seized materials.
• Government is eager to begin reviewing documents but judge tempers expectations—“everything is supposedly up in the air.” [35:39]

5. National Security/DOJ Investigations

[40:14–47:34]

• FBI Agent Firings:
  • DOJ purged agents working Iran counterespionage just days before U.S./Israeli strikes—a decision believed to have increased the real national security risk.
  • Troy Edwards points out institutional memory, relationships, and response speed are key in national security work.
• Auto-Pen “Scandal” Ends:
  • DOJ closes its investigation into whether President Biden’s use of an auto-pen to sign official documents was a crime.
  • “Investigators were never quite clear what crime, if any, had been committed…”
  • Even were there a crime, Presidential immunity would apply.
  • Parloff: “They were also supposed to go after aides…maybe the theory was you could find somebody that conspired to aid…”

6. Bar Discipline, DOJ Rulemaking, Halligan Investigation

[48:19–54:17]

• DOJ proposes a regulation to intervene in state bar disciplinary proceedings before state investigation.
• Investigations launched (or not) against DOJ attorney Lindsey Halligan for alleged professional misconduct in high-profile prosecutions—though the Florida bar now says there’s no pending investigation.
• Traditional DOJ stance: state bars should defer to internal Office of Professional Responsibility (OPR) reviews.

7. Press Access & New Pentagon Rules

[54:17–61:53]

• New DoD policy requires media to sign a 21-page agreement severely restricting news gathering—even off-record conversations—else lose press badges.
• Judge Friedman seems skeptical:

  “I’m not persuaded. All you have to do is say, 'I can’t answer the question,' but reporters have to be able to ask… That’s what the First Amendment is all about.” [60:04]

8. Immigration Litigation Firehose

[61:53–87:44]

• Refugee Suspension Upheld: 9th Circuit allows Trump’s blanket refugee admissions halt to stand for those not in the U.S. [62:57]
• Oversight Facility Access: Judge Jia Cobb again finds DHS cannot block members of Congress from entering ICE facilities with less than 7 days notice—DHS’s attempt to shuffle appropriations funds fails. [66:22]
• Minnesota Refugee Roundup Halted: Judge Tunheim enjoins new DHS practice of arresting all refugees on one-year anniversaries and “shipping them off to Texas.” [72:50]
• Contempt Hearings Proliferate: Minnesota judges summon ICE/DOJ over repeated failures to release property, follow release orders, or even keep people in-state.
  • Parloff:

    “Taking a man’s nail gun is low…that’s the tools of his trade.” [80:37]

• West Virginia Judges Furious: Systematic denial of due process in detention/bond hearings, despite repeated orders, triggers a “final notice" and threats of liability/contempt. [81:22]
• Three-Letter Case Updates:
  • JGG class: status reports dodged via appeal.
  • DVD class: summary judgment for petitioners, immediate appeal (and likely Supreme Court escalation).

Notable Quotes:

“You have to find the right plaintiff and the right legal organization…” – Alan Rosenstein on TikTok litigation [09:20]

“When Director Patel fires folks like this two to three days before US Israeli strikes on Iran…you can almost quantify the national security threat.” – Troy Edwards [40:55]

“Investigators were never quite clear what crime, if any, had been committed.” — NYT article, quoted by Parloff on the Biden-auto pen probe [44:24]

9. The Cri de Cœur ("Judicial Outcry") Roundup

[87:44–93:06] Lawfare launches its "Cri de Cœur Watch," highlighting pointed judicial denunciations of government misconduct.

• Judge Farbiars, Newark:
  17 ICE “no transfer” orders violated in a short time; moves to demand personal sign-off by ICE brass and warns of criminal contempt for “willful blindness.”
  • Parloff:

    “He will find them in criminal contempt on a willful blindness theory.” [90:45]

• Judge Gary Brown, E.D.N.Y.:
  SIJ (“special immigrant juvenile”) held, wrongly, then ICE tries to revoke work authorization and fine the victim.
  "This isn't how things are supposed to work in America. Unquestionably, the laws of human decency condemn such villainy.” [93:03]

Audience Q&A Highlights

• Court Orders & CBP Non-Compliance: No panelist had full details; to be revisited.
• Why call federal parties ‘the government’? – Custom/convention, even if imprecise.
• Efficacy of litigating immigration abuses:
  • “Courts get more conservative as you go up the ranks…” – Parloff [96:18]
  • Enormous cumulative effect at district court level, even if higher courts are more restrictive (Wittes).
  • Risks from jurisdiction-stripping provisions—Congress partly to blame.
• DFC & Trump’s tanker insurance: None of the panelists had the answer; suggestion to ask Lindsey Halligan, “insurance lawyer.”

Memorable Moments / Tone

• Informality: Frequent dry humor, e.g., code names (the Spider, the Jackal, etc.), panelists’ faux exasperation, and tongue-in-cheek commentary.
• Transparency & Frustration: Panelists call out DOJ “gamesmanship,” government indifference, and the toll taken on practitioners, judges, and the rule of law.
• Dark Comedy at Bureaucratic Absurdity: Buttressing serious analysis.

Notable Quotes with Timestamps

• “The government will likely argue that is not sufficient standing...it’s not the sort of particularized injury that is fairly traceable to him.” – Rosenstein [11:09]
• “If it somehow survives the kind of initial motions to dismiss, then we get into discovery territory and that gets real fun.” – Rosenstein [13:09]
• “I have seen the government drop appeals before... But I've never seen the government drop an appeal and then drop the dropping of the appeal.” – Wittes [26:49]
• “Taking a man's nail gun is low. …that’s the tools of his trade.” – Wittes [80:37]
• “This isn't how things are supposed to work in America. Unquestionably, the laws of human decency condemn such villainy.” – Judge Brown (quoted by Parloff) [92:22]

Segment Timestamps

| Topic | Start - End | |--------------------------------------------------|-----------------| | TikTok Litigation | 05:45–13:09 | | Anthropic v. DoD | 13:09–22:08 | | Don Lemon Case & DOJ Appellate Flip-Flop | 23:10–32:06 | | Fulton County / Mediator Appointment | 32:24–35:39 | | DOJ/FBI National Security / Agent Firings | 40:14–47:34 | | Bar Complaints / Halligan Investigation | 48:19–54:17 | | Press Access / DoD Press Rules | 54:17–61:53 | | Immigration Litigation Wave | 61:53–87:44 | | Cri de Cœur Watch (Judicial Outcries) | 87:44–93:06 | | Audience Q&A | 93:12–106:12 |

Summary Takeaways

• The Trump administration’s approach to law and policy is generating a barrage of complex, often unprecedented litigation.
• Courts—especially at the district level—are struggling, sometimes furiously, to keep basic constitutional guardrails on executive abuses, but structural and appellate barriers loom large.
• DOJ’s bureaucratic decisions, bar discipline games, and a wave of restrictive immigration policies reveal both legal vulnerabilities and windows for eventual judicial reckoning.
• Judicial patience, particularly in immigration and national security litigation, is wearing thin—often flickering into open judicial condemnation.
• The panel’s mix of expertise, candor, and gallows humor provides a rare, accessible education in the nuts-and-bolts of democracy’s legal emergency brake.