Why Are Chicago City Council Members Called Aldermen?
Plus, this week’s Rule O’ Law Roundup
Good Evening:
I took this picture with my phone, out of the window of my car moving at about 20 miles per hour (no, I wasn’t driving). The image is unaltered with any kind of filter.
Wednesday on #DogShirtTV, the estimable Holly Berkley Fletcher brought on the estimable Dan Kobayashi, a former State Department Africa analyst, to tell us about his departure from the State Department, the intelligence analysis group at the department—and the tiny African nation of Lesotho:
Thursday on #DogShirtTV, the estimable Mike Feinberg dragged us in to a discussion of movies that make you feel bad—and whether he should sandbag his long-suffering wife with one of the most depressing movies ever made:
Friday on #DogShirtTV, the estimable Keri Ladner joined us to discuss her book, American Dominion:
Recently On Lawfare
Compiled by the estimable Marissa Wang
Ukraine’s Energy Corruption Scandal Just Got Much Worse
The estimable Anastasiia Lapatina examines the evidence behind escalating corruption allegations against Ukrainian President Volodymyr Zelensky and his inner circle following the leak of wiretap transcripts from a major energy corruption investigation.
Don’t look now but the biggest corruption scandal in modern Ukrainian history is getting a whole lot worse. I wrote about this scandal—in which current and former Ukrainian officials, as well as the Ukrainian president’s close associates, allegedly exerted illegal influence over a strategic state-owned energy company to enrich themselves—last November. The scheme, revealed by the National Anti-Corruption Bureau of Ukraine, or NABU, led to the firing of two ministers and the president’s notorious chief of staff.
At the time, the scandal implicated a number of Volodymyr Zelensky’s close friends and associates, but it did not touch him personally.
All that changed two weeks ago, when Ukrainian media revealed previously undisclosed case files that potentially link Zelensky himself to the scheme and suggest that he may be getting a very nice house out of it.
Dominating AI Requires Understanding AI
Kevin Frazier and Alan Z. Rozenshtein argue that maintaining U.S. artificial intelligence (AI) dominance will require not only rapidly advancing frontier models, but also major investments in understanding, testing, and securing AI systems. The pair emphasize that breakthroughs in AI interpretability, cybersecurity, and public-private coordination are necessary to ensure both national security and long-term public trust in AI deployment.
A fundamental tension previously defined the artificial intelligence (AI) policy landscape: Proposals for the government to oversee testing and evaluation of frontier AI models were regarded as antithetical to rapid development and diffusion of the latest and greatest AI. This perceived trade-off split AI stakeholders into two camps: so-called doomers and accelerationists. The former lobbied for variants of predeployment testing of models by the government or some third party. The latter, including the Trump administration, advocated for American “global dominance” through limited government intervention until evidence indicated that existing law proved unable to steer AI efforts toward the nation’s broader economic and national security goals.
That era of AI policy looks like it has come to an end. The Trump administration has signaled—albeit inconsistently and ambiguously—its interest in a new path: dominating AI by understanding it.
Fewer Bots, More Ads: The Pentagon’s Evolving Online Influence Campaigns
Renée DiResta analyzes a new generation of Pentagon-linked online influence operations and traces how covert U.S. propaganda efforts evolved from fake social media personas and bot amplification into state-funded “news” sites promoted through paid advertising. DiResta explains that these outlets rely on selective framing and coordinated ad strategies to shape narratives about certain regions such as Latin America, Iran, and Ukraine.
This piece and the accompanying technical analysis report cover what appears to be a new, third generation of Pentagon information operations. This network of websites is less clearly attributed, but it also doesn’t appear to rely on fake personas or bot farms for promotion. Much of its content appears to be factually supportable—and, interestingly, users encountering its X accounts have asked Grok “is this true” a few dozen times. At least one post was Community Note-d, meaning that X users flagged it as misleading and provided additional contextualizing information. Its reach appears to come not from coordinated inauthentic amplification, but from paid advertising on major platforms—leading to tens of millions of views.
DHS’s Flawed Defense of Home Invasion Based on Administrative Warrants
Lindsay Nash examines the legal justifications behind a policy implemented recently by Immigrations and Customs Enforcement that would allow agents to enter homes with administrative warrants, a nonjudicial form that agents themselves sign off on. Nash argues that the policy misunderstands or misrepresents the legal arguments in support of administrative warrants.
Unsurprisingly, the abuses that early administrators feared now abound in immigration’s warrant-issuing scheme. In recent years, supervisors have doled out blank, presigned arrest warrant forms, agents have relied on warrants with blatant factual flaws, and ICE regularly attempts to rely on warrants that postdate the arrest for which they are required. Warrant-issuers even at the highest echelons of the department now look very different from the high-level “independent responsible” officer that Abel envisioned, as they have proudly demonstrated their failure to understand the basic constitutional requirements for these civil immigration arrests and the significant extent to which the president’s political agenda has dictated their arrest-related decisions. In short, the scale of warrant-issuing, the role of warrant-issuers, and the approach to warrant-issuing today make for a radically different context than the one in which Abel was decided.
Why Is the Weaponization Report So … Normal?
Kate Gilbert argues that the first report from the Department of Justice’s “Weaponization Working Group” incorporates a veneer of government-speak and effortful sourcing to normalize its architects’ likely intended goal of investigating and prosecuting former officials.
The report’s architects may also be contemplating their own futures. Just as the authors of Project 2025 thought about what they could accomplish in a favorable future administration, Trump administration officials may now be considering the ways in which an unfavorable future administration could seek accountability for current violations of law and policy. Perhaps in building a framework that could be used to investigate and prosecute former Justice Department officials, current department officials are considering their own future defense if they are later accused of malicious prosecution. Criminal lawyers are intimately familiar with the concept of mens rea, the guilty mind. It’s much easier to discern improper motivation in a vengeful social media post than it is in the report’s familiar government-speak, effortful sourcing, and claimed quantity of supportive material. In that sense, the “career employees” who allegedly participated in the writing of this report may even serve as rhetorical human shields, not only by lending legitimacy but also by blurring the boundaries of who should be held responsible for the report and what follows.
Don’t Count on Courts to Rein In Unregulated AI
Daniel Wilf-Townsend argues that the U.S. legal system is too slow to effectively regulate AI, as years of procedural delays have allowed the industry to grow so large that judges now face enormous pressure to rule in its favor to avoid economic catastrophe. He warns that this dynamic—where delay entrenches the status quo—is already shaping legal outcomes across copyright, tort, and other AI-related cases.
There are plenty of reasons for judges to want to take their time in these cases. These are complex and novel issues. Who wouldn’t want more time to learn about them and decide what the best outcome is? Who wouldn’t want to hear from a wide range of experts, gather all the conceivably relevant data, and make the most informed decision possible?
But there is a problem with the timelines that courts have been operating on. The problem is that the world keeps marching on, changing the environment in which these cases will be decided in ways that can influence the outcomes of the cases themselves.
Inside the World of Teen Cybercrime
Tash Buckley reviews Joe Tidy’s “Ctrl + Alt + Chaos: How Teenage Hijackers Hijack the Internet,” calling the book a vivid, narrative-driven account of teenage cybercrime culture that makes the human cost of cyberattacks feel real. While she praises Tidy’s storytelling, Buckley notes that the book leaves deeper questions unanswered about what drives socially isolated teenagers into serious cybercrime.
Tidy uses his account of Ransom_man, that is, Julius Kivimäki, in order to sketch a demographic and psychological portrait of the group of teenage hackers who have played an outsize role in pioneering many types of cybercrime. That portrait is striking in its consistency. Usually male, often white, frequently from a reasonably stable home environment, these hackers begin their exploits in their teens. Some have an illness that keeps them housebound; others are simply left alone in their bedrooms for long stretches of time. But their most consistent features are social isolation and a deep immersion in computer gaming.
Tidy is careful to note that the vast majority of young people who fit this profile never come anywhere near cybercrime. Yet that caveat only sharpens the question he leaves hanging: What is it, exactly, that tips a socially isolated teenage gamer into becoming a callous and prolific hacker? Infamy, Tidy suggests, can become its own reward. He makes a convincing case that lenient sentencing has compounded the problem considerably: When the worst realistic outcome is a confiscated laptop and a suspended sentence, the deterrent effect is minimal.
The AI Regulation Knife Fight
In the latest edition of the Seriously Risky Business newsletter, Tom Uren reports on the chaotic internal debate within the Trump administration over AI model oversight, how threat actors are exploiting free-trial loopholes to bypass AI safety guardrails at scale, Russia’s nascent Starlink rival satellite constellation, and more.
Of course, AI is about more than just cybersecurity and potentially has serious implications across the entire economy. There is no single government agency that contains all the expertise needed to review models. For example, AI companies are concerned about the biological and chemical capabilities of models and whether they could be used to assist in the creation of weapons of mass destruction. These are serious concerns but not exactly the expertise that the National Security Agency holds.
Despite that, the intelligence community should obviously be involved in assessing models. Where the specialist expertise exists in that community, the U.S. government should draw on it. But the intelligence community shouldn’t own model assessment entirely. AI’s implications are simply too wide-ranging.
Podcasts
Lawfare Daily: Terrorism and Insurgency in sub-Saharan Africa: Daniel Byman sits down with Holly Berkley Fletcher and Alexander Palmer to discuss the growth of terrorism and instability in East and West Africa, the instability of regional governments, and how the U.S. and other outside powers are shaping the region.
Lawfare Daily: Rep. Sara Jacobs (D-CA) on Congress’s Role in Foreign Affairs: Scott R. Anderson sits down with Rep. Sara Jacobs (D-Calif.) to discuss her and her colleague’s efforts to oppose the Iran war, bipartisan proposals relating to foreign assistance and expeditionary diplomacy, the role a Congress under Democratic leadership could play during the second Trump administration, and more.
Lawfare Daily: Danylo Mokryk on Domestic Ukrainian Politics: Anastasiia Lapatina sits down with Danylo Mokryk to discuss the latest corruption scandal surrounding the Ukrainian government, evidence suggesting that Ukrainian President Volodymyr Zelensky personally profited from corruption, and why—despite this evidence—no one is calling for Zelensky’s removal.
Scaling Laws: Escaping One-Size-Fits-All AI Policy with Sean Perryman: Kevin Frazier and Sean Perryman unpack the rapidly evolving debate over algorithmic pricing and AI governance. They discuss state-level efforts to regulate algorithmic pricing, political motivations behind these regulatory efforts, the economic tradeoffs they often overlook, and the risk of unintended consequences.
Videos
On May 15 at 4 pm ET, I sat down with Anna Bower, Eric Columbus, and Roger Parloff to discuss the Justice Department’s lawsuit against the D.C. Bar for disciplining Jeffery Clark, oral argument before the D.C. Circuit Court of Appeals in the lawsuit challenging the executive orders targeting law firms, and more.
Today’s #BeastOfTheDay is a cat from Deventer in the Netherlands, circa 1420. As you all should know, dogs and cats are only eligible to be Beasts of the Day if they perform an Act of Valor. Today’s Beast performed its Act of Valor by enraging a monk. Here is a drawing of today’s Beast by the monk in question:
The text written sideways as a caption to the image of today’s Beast reads
Hic non defectus est, sed cattus minxit desuper nocte quadam. Confundatur pessimus cattus qui minxit super librum istum in nocte Daventrie, et consimiliter omnes alii propter illum. Et cavendum valde ne permittantur libri aperti per noctem ubi cattie venire possunt.
which translates to
Nothing is omitted here, but a cat urinated on this one night. Accursed is the wicked cat that urinated over this book during the night in Deventer and every other cat like it. And beware well not to leave books open at night anywhere cats are allowed in.
In honor of today’s Beast, find a cat and curse at it.
The Rule O’ Law Roundup, May 17, 2026
Perkins Coie LLP v. United States Department of Justice, No. 25-5241 (consolidated with Jenner & Block, WilmerHale, and Susman Godfrey appeals); Zaid v. Executive Office of the President, No. 26-5009 (D.C. Cir., oral argument)
The D.C. Circuit on Wednesday, May 14, heard back-to-back oral arguments in the consolidated appeals from the four district-court decisions striking down the President’s executive orders targeting the law firms Perkins Coie, Jenner & Block, WilmerHale, and Susman Godfrey, and in the parallel appeal in the security-clearance retaliation case brought by national-security lawyer Mark Zaid. The panel was Chief Judge Sri Srinivasan (Obama), Circuit Judge Cornelia Pillard (Obama), and Circuit Judge Neomi Rao (Trump).
Paul D. Clement of Clement & Murphy argued for the four firms; Mark Zaid argued for himself in the second appeal. Deputy Assistant Attorney General Abhishek Kambli argued for the United States in both.
The panel seemed skeptical of the government’s defense of the orders. Clement reframed the government’s theory as a presidential license to retaliate against “law firms that represent Democrats,” and pressed the panel on whether the same logic would permit retaliation against any firm whose pro bono docket displeased the executive. Judge Rao, the panel’s most likely vote for the government, focused her questioning on the limits of judicial review of security-clearance decisions—a potential off-ramp the panel could give the government in the Zaid half of the argument without reaching the broader First Amendment question.
A moment of pure comedy occurred right at the outset of the law firm argument, when Kambli declared: “The power to determine who gets to access classified information has never been circumcised by Congress, which is another reason why it’s dedicated to the executive” (see timestamp: 2 minutes, 28 seconds).
Keep reading with a 7-day free trial
Subscribe to Dog Shirt Daily to keep reading this post and get 7 days of free access to the full post archives.
 | A guest post by
|