The Rule O’ Law Roundup, May 24, 2006

And a stuffed black and white cookie

Good Evening:

In case what was missing from your life was a stuffed black and white cookie with legs, FAO Schwartz has you covered.

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Tuesday on #DogShirtTV, the estimable Holly Berkley Fletcher and the estimable Eve gaumond came on to talk about all the various aspects of the global economy that Trump is wrecking:

Wednesday on #DogShirtTV, I celebrated not getting arrested during my Special Military Operation at the Justice Department with a detailed discussion of all the ways the Justice Department is collapsing and chat with the estimable Andrew Steele about Todd Blanche’s testimony the previous day:

Thursday on #DogShirtTV, the estimable Stacey Young came on the show to tell us about her organization, Justice Connection, and our joint escapade with a projector and a John Adams quotation:

Friday on #DogShirtTV, I revisited an old piece on anti-semitism:

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Recently On Lawfare

Compiled by the estimable Marissa Wang

The Deal Washington Cannot Broker

Dmytro Soldatenko argues that Russia’s underlying goal in international negotiations is to normalize its invasion of Ukraine by dismantling the legal record of international law that defines the war as unlawful aggression. Soldatenko contends that Ukraine’s strongest leverage lies in sustaining this international law framework.

Russia has consistently challenged the legitimacy of international determinations that characterize its actions in Ukraine as violations of international law. Beyond that, it advocates withdrawing claims and investigations before international tribunals and halting new General Assembly resolutions that extend the record. The Kremlin also demands the lifting of sanctions on Russian assets and persons enacted in response to the record. Yet the role of that record and the normalization Russia demands is underexplored in the current public debate on the peace process. This piece argues that the legal record is not a peripheral item on Russia’s list of conditions: It is the element that enables the entire architecture of costs imposed on Russia for its aggression. The legal record is also a dimension where Ukraine could negotiate from a position of strength, for instance, by deferring recurring UN resolutions in exchange for concessions that the current structure of negotiations lacks.

Not reckoning with this dimension while pushing Ukraine toward territorial concessions risks undermining the very instrument that generates long-term costs for Moscow without delivering the normalization Russia actually seeks.

The AI Race Isn’t Real

Yonathan A. Arbel and Matthew Tokson explain that framing U.S.-China artificial intelligence (AI) competition as a “race” is descriptively flawed and strategically dangerous. The pair unpack how the race narrative encourages deregulation, weakens AI safety standards, and escalates geopolitical tensions while overlooking alternative, collaboration-focused approaches.

In short, the benefits of “winning” the AI race are far smaller and more temporary than those adopting the race metaphor appreciate. And the costs of racing are potentially massive, ranging from devastating attacks by rogue organizations, to an elevated risk of global war, to human extinction itself. The right response is not to run faster, but to recognize that the race concept itself is the problem.

Strip away the race metaphor, and options that were obfuscated come into clear view. Cooperation on safety standards, measured pacing of frontier development, catalytic regulation, international agreements on military AI: None of these is conceivable if the only question is who crosses the finish line first. But there is no finish line. Once that becomes clear, the full range of policy tools becomes available again. In our forthcoming article, we develop this alternative vision: American AI leadership defined by effectiveness and safety.

The President Who Sued Himself

Anna Bower and Eric Columbus unpack President Trump’s settlement agreement in his lawsuit against the IRS, the legal framework for the recently announced Anti-Weaponization Fund, acting Attorney General Todd Blanche’s order that purports to extend immunity from government liability to Trump and his family, and more. Bower and Columbus framed these recent executive actions as part of a larger effort under the Trump administration to strengthen the presidency’s oversight of the Department of Justice.

Against that backdrop, perhaps it should come as no surprise that one of the most breathtakingly corrupt episodes of Trump’s second term began with a lawsuit he filed against the very government he now controls. On Jan. 29, 2026, Trump—joined by his two eldest sons and the Trump Organization—filed a suit against the IRS and the Treasury Department. They claimed that a former IRS contractor, Charles Littlejohn, had illegally disclosed Trump’s tax return information to the New York Times and other media outlets. Trump said any money he makes off of this suit would go to charity.

As it turns out, his political allies are the “charity,” and American taxpayers are the donors.

Earlier this week, the Justice Department announced that Acting Attorney General Todd Blanche had established a $1.776 billion dollar fund, ostensibly as part of a settlement agreement in Trump v. IRS. The fund—drawn entirely from the federal Judgment Fund, a permanent congressional appropriation used to pay court settlements against the United States—will be used to dispense taxpayer money to people who suffered from purported Democratic “weaponization” and “lawfare.” While Trump is not expected to receive compensation from the fund himself, money will be doled out by a five-member board he effectively controls, operating under procedures that need not be disclosed, with the identities of recipients potentially kept secret.

The name Trump chose for this instrument of partisan self-dealing—conjured by a president suing his own government and settling with himself, a product of the politicized use of the legal system he claims to deplore—is “The Anti-Weaponization Fund.”

Advice and Consent for Major Governmental AI Deployments

Cullen O’Keefe argues that Congress should require the executive branch to obtain explicit congressional approval before deploying advanced AI systems in high-risk governmental functions. O’Keefe explains that large-scale governmental AI systems could weaken traditional checks on executive power and threaten democratic accountability.

The future of U.S. state capacity requires ambitious government deployment of AI, and American liberty requires careful regulation of that deployment. Managing this tension will be a central task in the coming decades.

While no single mechanism will suffice, active congressional oversight of the executive branch’s AI use will remain indispensable. Given the speed and scale at which AI can act, prospective approval will be at least as important as retrospective review. Before the executive branch is allowed to use AI for its most significant functions—those that threaten to deprive the people of their life, liberty, and property—the specific consent of the people’s representatives should be obtained.

Pressure Without Pause: Iraq’s Role in the Postwar Iran Settlement

Omar Mohammed argues that the U.S. should maintain sustained pressure on Iranian-backed militias embedded within Iraq because these groups are Tehran’s strongest remaining source of regional influence following the conclusion of Operation Epic Fury. Mohammed explains that weakening the militias through sanctions and economic leverage is necessary to preserve Iraqi sovereignty and prevent further Iranian influence over Iraq’s political and security systems.

​What the war did not end is the Iran-aligned militia infrastructure inside Iraq. That infrastructure is the asset of Tehran’s foreign-operations apparatus that the campaign deliberately left in place. U.S. and Israeli targeting was concentrated on Iran proper and on assets clearly identifiable as IRGC-Quds Force, both to avoid striking elements legally embedded in the Iraqi state and to preserve Baghdad’s nominal neutrality in the war. The militias were therefore the instrument with the most intact capacity to reconstitute Iranian regional leverage in the postwar period. Reporting during the war also revealed clandestine Israeli operational infrastructure on Iraqi soil—a development that complicates the sovereignty framing but does not alter the underlying dynamic. Iraq’s territory has been a contested arena of regional war precisely because the Iraqi state does not control the armed actors operating from it.

Has Russia Overplayed Its Hand in UN Cyber Negotiations?

Pavlina Pavlova, Christopher Painter, and Nick Ashton-Hart examine how Russia has failed to fully impose its authoritarian vision on the substance of international cyber agreements, despite its successful push for negotiations with the UN. The trio contend that, while democratic states have so far blocked many of the most restrictive proposals, these states must develop a proactive cyber governance agenda focused on international cooperation and humanitarian values to respond to Russia and China’s efforts.

However, Russia and China are playing the long game, often in tandem, and, buoyed by recent wins, they will continue to use UN fora to achieve their aims––authoritarian-leaning governance institutionalized through international frameworks, limits on technology they will advocate for but not comply with, and restrictions on expression and human rights they deem as threats to their regimes. Accordingly, democratic countries cannot define their ambition by blocking potentially harmful procedural moves alone. They need to engage in multilateral processes with strategic discipline: anticipate procedural moves, build coalitions on substantive matters before votes are called, and develop a compelling agenda that offers a credible response to rising cyber insecurity.

R.I.P. Chicago Protester Prosecution (2025-2026)

Eric Columbus unpacks the Department of Justice’s prosecution of the Broadview, Illinois, ICE protestors, from its start with Operation Midway Blitz to its final hearing on May 21, where a federal judge dismissed the charges. Columbus argues that the prosecution of the “Broadview Four” reflects the growing politicization and overreach of federal immigration enforcement under the Trump administration and underscores broader concerns about the erosion of the rule of law at the Justice Department.

Yesterday, at the end of a dramatic hearing at which a federal judge revealed improper prosecutorial conduct, the government dismissed charges against four protesters arising out of an incident outside of a Immigration and Customs Enforcement (ICE) holding facility in Broadview, just outside of Chicago. It was the final twist in a case that was both highly unusual and yet emblematic of the Trump administration’s troubles in trying to make criminal charges against its antagonists stick.

This is the story of that case, from birth to death.

The Anti-Weaponization Fund and the History of Abusive Federal Settlements

Aziz Huq explains that the Trump administration’s new Anti-Weaponization Fund is not only a legally questionable use of the Justice Department’s settlement authority, but also reflects a broader historical pattern of administrations using federal settlements for political purposes. Huq contends that any meaningful remedy will likely require congressional action, as courts may lack a clear path to challenge the fund.

Nevertheless, it would be a mistake to chalk up the fund as simply another case in which the Trump administration has broken new ground by ignoring the law, or by finding a new way to twist a legal authority to unethical or improper ends. Rather, the fund is an instance in which a loosely drafted set of statutes has long been misused by administrations of both stripes. (The immunization of the Trump family from tax-related review is another matter.) Blanche’s proposed misuse of his settlement authority may be particularly objectionable because he is planning to reward violent, anti-democratic lawbreakers—but that does not mean the basic distortion of the legal system is novel.

Politicians to Ditch Signal for Homegrown Apps

In the latest edition of the Seriously Risky Business cybersecurity newsletter, Tom Uren examines the European government’s shift away from international encrypted messaging apps for domestic platforms where they can maintain sovereign control, the recently released details on an early 21st century cyber operations campaign designed to slow Iranian nuclear development, and more.

In recent weeks, details have come to light about the cyber operations campaign intended to slow Iran’s development of nuclear weapons in the mid-to-late 2000s.

The overall campaign was intended to stop or slow Iran’s nuclear weapons development program, and we’ve recently learned that the infamous Stuxnet worm was just one arm of a two-pronged effort.

Documents

Marissa Wang shares the unsealed superseding indictment charging former Cuban President Raúl Castro and five Cuban air force pilots for their alleged roles in the shoot down of two civilian flown planes in 1996, killing four U.S. nationals.

Podcasts

Lawfare Daily: The Costs (and Cultural Cachet) of the Cambridge Spies: Antonia Senior joins Michael Feinberg to discuss Senior’s new book, “Stalin’s Apostles: The Cambridge Five and the Making of the Soviet Empire,” on the history of the Cambridge spy ring. The pair unpacked the history of the Cambridge Five, how they were recruited, how the group was discovered, and their lasting effect on the culture of espionage.

Scaling Laws: Let’s Do the Science! Talking Algorithms with Cathy O’Neill: Kevin Frazier sits down with Cathy O’Neil to discuss the capabilities and limitations of algorithmic auditing, how organizations measure and mitigate bias, where auditing should fit into broader governance frameworks, and more.

Lawfare Daily: ‘The Warhead’ with Jeffery Stern: Loren Voss sits down with Jeffrey Stern to discuss Stern’s new book, “The Warhead: The Quest to Build the Perfect Weapon in the Age of Modern Warfare.” Their conversation covers the development of the Paveway bomb, the importance of precision weapons to modern warfare, the War Powers Resolution, and more.

Lawfare Daily: Ancient China and Modern Politics: Daniel Bell joins Michael Feinberg to discuss Bell’s new book, “Why Ancient Chinese Political Thought Matters: Four Dialogues on China’s Past, Present, and Future.” The pair discuss the ongoing influence of ancient Chinese political theory on modern China and its domestic debates.

Rational Security: The “No Banner is Safe” Edition: Scott R. Anderson sits down with me and Kari Heerman to unpack President Trump’s trip to Beijing to meet with Chinese President Xi Jinping, rising U.S. pressure on Cuba, another legal strikedown of Trump’s tariffs, and more.

Lawfare No Bull: Anthropic v. Hegseth and DOD at the D.C. Circuit: Wang shares audio from the oral argument in Anthropic’s lawsuit against the Department of Defense and Secretary of Defense Pete Hegseth for their designation of the artificial intelligence company as a supply chain risk.

Lawfare Daily: Trump Sues Self, Settles: Columbus joins me to unpack the settlement in the Trump family’s lawsuit against the IRS and the Department of Treasury that has led to the creation of a $1.776 “anti-weaponization fund” and a promise of blanket immunity from government liability for President Trump and his family.

Scaling Laws: The Politics of Data Centers with VA Delegate John McAuliff: Kevin Frazier sits down with John McAuliff to discuss the ongoing debates around data centers at the state level, including what state legislatures are doing to help counties negotiate with data center developers and why their development is a key issue for voters.

Videos

At 4 pm ET on May 22, I sat down with Anna Bower, Roger Parloff, and Columbus to discuss the Department of Justice’s Anti-Weaponization Fund, oral argument in Anthropic’s lawsuit at the D.C. Circuit Court of Appeals, and more.

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Today’s #BeastOfTheDay is the goose, seen here demonstrating the downside of hollow bones:

Video Source

I’ll be honest with you: I, EJ Wittes, am profoundly irritated by today’s Beasts. It would be so simple for today’s Beasts to be ducklings that were being blown around instead of goslings. Then I could make a joke about “getting one’s ducks in a row” and it would all be neat and tidy. But no. Today’s Beasts are disobligingly geese.

I have no suggestions to make about appropriate ways to honor today’s Beasts. Today’s Beasts are unworthy of honor. If they wanted honor, they should have been ducks.

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The Rule O’ Law Roundup, May 24, 2026

• United States v. Abrego Garcia, No. 3:25-cr-00115 (M.D. Tenn., May 22, 2026, U.S. District Judge Waverly Crenshaw, Jr.)

On Friday, May 22, U.S. District Judge Waverly D. Crenshaw, Jr. dismissed the two-count human-smuggling indictment against Kilmar Armando Abrego Garcia, granting a Rule 12(b)(3)(A)(iv) motion to dismiss for vindictive and selective prosecution. As the court framed it, the motion “arises from the Executive Branch’s response to [Abrego Garcia’s] lawsuit challenging his wrongful removal” to El Salvador — that is, the defendant’s claim was that he was prosecuted in response to his exercise of his rights in court.