The Lawfare Podcast: Lawfare Daily - The Trials of the Trump Administration

Date: September 8, 2025
Host: Benjamin Wittes (Editor-in-Chief, Lawfare)
Panel: Scott R. Anderson (Senior Editor), Roger Parloff (Senior Editor), Lauren Voss (Public Service Fellow), Katherine Jan Ebright (Counsel, Brennan Center for Justice)

Main Theme

This episode offers an in-depth roundup and analysis of numerous ongoing legal and policy battles during the Trump Administration’s second term. The panel explores the legal and political skirmishes over the deployment of federal and National Guard forces in Washington, D.C., significant court rulings on presidential powers and immigration, Harvard’s win over a federal funding cut, the government’s use of the Alien Enemies Act against Venezuelan nationals, and high-stakes litigation concerning the spending or withholding of federal grants and appropriations.

The conversation blends legal analysis, strategic speculation, and pointed commentary on a tumultuous period in American governance.

Key Discussion Points & Insights

1. Quick Updates: “Boat Boom” & Guatemalan Children Cases

[02:03 - 11:30]

• War Powers Report on “Boat Boom”:

  • The administration’s War Powers report on the destruction of the “Tren de Aragua” speedboat was leaked before official release (seen on Bluesky).
  • The report relies on the President’s Article II authority, focuses on self-defense (“against narcotics trafficking, unlawful migration, and violent criminal activity”), with nods to regional instability and the ‘unable or unwilling’ doctrine, which could pave the way for military actions in other countries like Venezuela.
  • Scott R. Anderson: “The letter essentially confirmed the administration is relying upon the President’s Article 2 constitutional authority to pursue this particular military action..." [05:44]
  • Other countries are described as “unable or unwilling to adequately address the threat,” a justification used previously in Syria.
  • Discussion: The lack of clear legal basis and international law justification is considered potentially dangerous.

• Guatemalan Children Litigation:

  • Passing update: Awaiting the government’s formal explanation for weekend actions, with motions for preliminary injunction and class certification pending.
  • Roger Parloff: “There hasn’t been a formal class certification yet… So, and then we’ll have a hearing on Wednesday at 2 in front of Judge Kelly.” [09:41]
  • Reference: For those wanting more detail, see Lawfare’s prior coverage and liveblogs.

2. Major Segment: The D.C. National Guard “Occupation”—Legal and Political Dimensions

[11:30 - 22:33]

• D.C. Mayor’s Position:

  • Mayor Bowser issued an executive order pledging cooperation with federal law enforcement “to the maximum extent allowable by D.C. law,” widely seen as a strategic move to stay on legal ground while protecting local interests.
  • Scott R. Anderson: Explains the legal authorities at play: the President can request services from the Metropolitan Police Department for federal purposes, citing DC code, and can activate the D.C. National Guard (operating in a quasi-state role).
  • The deployment of federal forces and National Guard is “exceptional” in scale and justification, but not unprecedented.
  • Quote: “...cooperate with federal law enforcement purposes to the extent allowed by D.C. law, meaning if D.C. law prohibits it, I’m not going to be able to do it.” [16:04]
  • Budget and personnel constraints, as well as concerns about ICE and aggressive federal tactics, are shaping city responses.
  • Wittes (humorous): “Is this a... hostage video by the mayor... or should we assume this is something else?” [13:05]

• Political Analysis:

  • Is the D.C. Attorney General acting as a “bad cop” to Bowser’s “good cop,” or pursuing a separate agenda?
  • Lauren Voss: “It’s just really unclear how these things fit together… from a political standpoint, it’s really unclear.” [25:12]

3. D.C. Attorney General’s Lawsuit Over National Guard Deployment

[22:33 - 45:10]

• Basis of the Lawsuit:

  • Seeks declaratory and injunctive relief, raises four claims: APA violation (“contrary to law” and “arbitrary/capricious”), constitutional violations (separation of powers, Take Care Clause, District Clause), and “ultra vires” action.
  • Challenges mobilization of the D.C. National Guard and out-of-state Guard under Title 32 as federal law enforcement, claiming it usurps local control and Home Rule.
  • Relies on arguments about the Emergency Management Assistance Compact (EMAC), and states that only the mayor should approve out-of-state Guard deployments.
  • Voss: “There isn’t clear evidence that this is the only way to do Title 32 deployment... I think that'll probably be the argument in response.” [32:35]
  • Lawsuit claims violation of Posse Comitatus and 10 USC 275. Legal experts seem unconvinced by some of these statutory arguments and suggest these may be untested executive practices the DoD would rather avoid judicial scrutiny over.

• Strategic Speculation:

  • This may be more than a symbolic gesture—could be a lever for negotiation or to force the Executive Branch into clarifying or scaling back its claimed powers.
  • Scott R. Anderson: “I do think it means they may have thought through some of this a little bit... A lot of the reasonable arguments... are well established in Defense Department and executive branch practice. None... have been subjected to judicial scrutiny.” [41:15]
  • Risk of adverse precedent if courts rule against D.C. sovereignty claims.

4. Major Court Decisions: Federal Authority, Immigration, and Presidential Powers

[45:10 - 72:17]

a) National Guard and PCA Litigation in LA & California

[45:10 - 46:49]

• Quick update: Ninth Circuit stayed Judge Breyer’s injunction against military law enforcement in California, no reasoning offered.

b) Fifth Circuit Blocks Alien Enemies Act Deportations

[46:49 - 63:50]

• Background: The Alien Enemies Act was invoked by President Trump to detain and deport Venezuelans believed to be connected to the “Tren de Aragua” gang, arguing their activity constitutes a “predatory incursion.”
• Ruling: 2-1 decision blocks the administration, holding that:
  • Courts cannot second-guess the facts stated in a presidential proclamation (factual findings), but can review whether those facts meet the legal criteria (“invasion,” “predatory incursion,” etc.).
  • “Invasion” and “predatory incursion” require organized military attack; migration and gang crime do not qualify.
  • Due process requires enough time for habeas relief, remanded for fact finding.
  • Catherine Jan Ebright: "The court... concludes that those terms are referring to military action by some organized, substantial... armed force. Migration is not that kind of attack." [53:49]
  • Dissent argued for even greater deference to the President.
  • Amicus brief by Ebright and colleagues referenced (and chided by the dissent), defending judicial review even in national security cases.

c) Forecast for the Supreme Court

[64:51 - 70:57]

• Panelists cautiously optimistic that the current Supreme Court, given the text and history of the Alien Enemies Act, will reject unfettered presidential discretion in this context.
  • Ebright: “I feel pretty good about this... how clear-cut it is that this is a wartime statute... it’s the last remaining part of the Alien and Sedition Acts … I think the odds are pretty good.” [68:39]

5. Immigration, TPS & Funding Litigation

[72:17 - 86:20]

• Abrego García Case and Deportation Targets:

  • The government continues to shift positions on where to deport high-profile detainees, leveraging terrorist designations as grounds for ineligibility for asylum.

• TPS (Temporary Protected Status) Program:

  • Judge Chen (N.D. Cal.) declares government’s cancellation of TPS for Venezuelans and Haitians “pretextual,” enjoining the action, affecting hundreds of thousands.

• Harvard’s First Amendment Win:

  • Judge Burroughs rules Harvard’s funding cut-off (for not acceding to demanded viewpoint audits and shifts under the guise of combating antisemitism) was a violation of the First Amendment.
  • The case raises complex jurisdictional issues, but First Amendment issues distinguished from recent Supreme Court rulings.
  • Parloff: “It’s a gutsy ruling, but... the fact that you can’t get, you know, relief is excruciating.” [85:05]
  • Wittes: “She’s trying to hold a line that may not hold.” [86:17]

• Other Grant Disputes—Climate and AIDS Funds:

  • Ongoing appellate litigation over whether plaintiffs must sue in district courts or the Court of Federal Claims to challenge federal grants being withheld/canceled; D.C. Circuit issues split decisions, with major implications for administrative remedies and funding for major programs.

6. Listener Q&A

[94:47 - 102:43]

• Legal Limits on Military Action Against Individuals Abroad:

  • Killing of alleged gang members like Kilmar Abrego in foreign countries presents significant legal and sovereignty issues—especially outside "hot pursuit" scenarios or international waters.

• Posse Comitatus and the Protective Power:

  • No clear bright-line rule barring use of troops as law enforcement for “protection.” Existing law allows military support to law enforcement, up to the blurry PCA line, but a clearer, more restrictive rule would represent a big departure from practice.

• SCOTUS Timeline for Cert Petitions:

  • Expedites are possible but not guaranteed; would depend on practical urgency and whether the government presses its case for expedition.

Notable Quotes & Moments

• Anderson on Legal Justification for Military Action:

  • “The letter essentially confirmed the administration is relying upon the President’s Article 2 constitutional authority...” [05:44]

• Wittes on D.C. Mayor’s Executive Order:

  • “Is this a... hostage video by the mayor... or should we assume this is something else?” [13:05]

• Voss on Attorney General’s Lawsuit:

  • “There isn't clear evidence that this is the only way to do Title 32 deployment… I think that'll probably be the argument in response.” [32:35]

• Ebright on Alien Enemies Act “Invasion” Standard:

  • “The court… concludes that [invasion and predatory incursion] are referring to military action by some organized, substantial… armed force. Migration is not that kind of attack…” [53:49]

• Ebright, on Dissent’s Extreme Deference:

  • “Even if the odds of invasion are 0.00000001%, we would contravene clear Supreme Court precedent if we were to countermand his determination…” [57:58]

• Parloff on Harvard Ruling:

  • “It’s a gutsy ruling, but... the fact that you can’t get, you know, relief is excruciating.” [85:05]

Timestamps for Major Segments

• Intro & Announcements: 00:00 – 02:03
• “Boat Boom” War Powers Analysis: 02:03 – 08:59
• Guatemalan Children Litigation Update: 08:59 – 11:30
• D.C. National Guard & Mayor’s Order: 11:30 – 22:33
• Attorney General’s NG Lawsuit: 22:33 – 45:10
• West Coast—Breyer’s Injunction Stayed: 45:10 – 46:49
• Fifth Circuit Blocks AEA Removals: 46:49 – 63:50
• Supreme Court/Future of AEA Power: 63:50 – 70:57
• TPS, Abrego, and Funding Cases (Harvard, Grants, AIDS): 72:17 – 86:20
• Listener Questions: 94:47 – 102:43

Tone & Language

Serious, technically detailed, and at times sardonic—especially when highlighting the stakes, legal ambiguities, or perceived absurdities in government arguments and judicial reasoning. The panel combines academic legal analysis, practical concerns, and political realpolitik, staying focused and incisive throughout.

Summary Takeaway

This episode is a rapid-fire, high-level tour through legal battles at the heart of current U.S. governance: executive military authority, federal/local balance, immigration, culture-war flashpoints at universities, and the power of judicial review against an emboldened presidency. Legal fault lines and constitutional questions abound, with key doctrines and real-world consequences for millions in the balance. The Lawfare team both informs and interrogates, inviting listeners to grapple with the logic, risks, and limits of the law in a polarized era.