GeoLegal Weekly #51-LegalAI in Trumpian Times
This week I wonder if new legal technologies will cure or quell the erosion of rights of many individuals and groups we have seen in recent days.
To some, Monday was the beginning of Making America Great Again. To others, it most certainly was not. You are probably swimming in breathless analysis of everything President Donald Trump did during his first day in office. I wrote my own piece in Barron’s yesterday situating Trump’s opening executive orders in the context of “unruliness,” the thesis that underlies my new book. Rather than restate it here, give the Barron’s piece a quick read to understand the broader context.
Trump’s actions attempt to dramatically change the rights of many groups and their recourse to legal support. This is purposeful and, for his supporters, it is something to cheer. When this happened in Trump’s prior term, however, many lawyers stepped in to fight back on behalf of these groups.
reminded me recently of how lawyers flocked to JFK airport when Trump put in place his “Muslim travel ban” in 2017 to help those affected.But in 2025, it might not be actual lawyers fighting back: Will legal robots (or founders building them) do the same for newly challenged groups?
Below, I’ll go over a handful of LegalAI approaches that could safeguard and restore the rights of those that fall victim to political battles - or, more practically, could be pretty good business models or pro bono projects for founders and law firms.
Unruling the rights of individuals
The legal system is about to become ground zero of policy arbitration in a way it has not been before. The president has turned up executive orders and pardons “to 11”—pushing the limits of presidential power in order to test if there are actually any limits. A central thrust of this is the freezing or elimination of government programs meant to safeguard civil rights, diversity, and obligations to immigrants.
To Trump’s supporters, this is a feature, not a bug. To them, this is about making America more merit-based and putting the rights of current Americans first. To those on the other side, this is something like checkmate of the disadvantaged in a chess game that has always been rigged.
In just the last few days, Trump has:
Eliminated legal aid programs for undocumented immigrants while simultaneously threatening mass deportations.
Frozen civil rights litigation, settlements and consent decrees by the Justice Department, with the implication being that the federal government is no longer interested in safeguarding those rights.
Threatened state and local officials who attempt to thwart deportation policy with criminal liability, mirroring threats to employers of undocumented immigrants.
Shut down the admission of refugees into the United States and turned off an app that had processed up to a million asylum seekers in the last year.
Began to fire everyone working in DEI in the government
Thrust American society back into binary definitions of gender rooted in biological sex at birth, threatening protections for transgender or non-binary persons.
It’s not clear what all of this will mean in practice. At the very least, these orders will likely lead to some services currently provided by the government going away. For some things, that may be ok: Just because something “is” today does not mean it should be tomorrow. But for others it may leave a very real gap in something that has been filled by the government whether or not you think the government should have filled that gap.
The questions, then, are: Does this gap need to be filled? Is there a real need? If so, who might fill it? Concerned citizens? State and local governments? Non-profits? Foreign governments? Businesses?
It could be any of them and depending on who takes it up, that could lead to very different types of outcomes. What I want to focus on today is can legal technology fill that gap?
LegalAI could level the playing field
A big part of my thesis in both the book and this newsletter has been that new legal technologies will step in to empower individuals in previously unthinkable ways. So when I see a churn in individual rights I immediately think about how tech can reverse that.
Those in the legal community who want to ensure that individuals get a fair hearing when massive shifts in policy threaten their legal or employment status don’t need to just throw hours at the problem. They can build solutions that scale for maximum impact.
What can legal technology do and what are the implications? Below I list a few ideas but I’m sure you’ll have more and I invite you to comment below:
Lawyer matching platforms: No doubt pro-bono oriented software platforms like Paladin will be a critical piece of the solution to mobilizing legal support in this environment. However, there are also a number of for-profit oriented legal marketplaces with thousands of lawyers who might be willing to step in to provide pro bono support across any of the topics listed above. This is not a problem of technology; this is a challenge of economics and bandwidth where founders who could make a very real contribution to the protection of rights will have to decide whether to invest in product tweaks in that direction and mobilize their communities to provide support. Those that do will have tremendous impact but they will also face political risk as they are swimming upstream against the political direction of travel.
Whistleblowing platforms: Seeing something and saying something is pretty problematic in an era where political and legal retribution will follow swiftly. But making it easier for whistleblowers to call out egregious trampling of rights will enhance protections of those affected. Time Magazine recently profiled one platform, Psst, which can anonymously match up multiple parties blowing the whistle on the same offender. Approaches like this will provide decentralized checks on extra-legal actions. I suspect in a government context using such platforms will raise claims of divulging classified information and the like; however, I also suspect such services will be ringing off the hook in coming months.
Multilingual AI-chat via text message: If you were an asylum seeker who just found out your appointment was cancelled, you’d wonder where you can turn. With legal aid for those on the other side of the border being terminated, AI may provide a substitute for such assessments. There have been a handful of legal information systems released in recent years as well as extremely powerful foundational LLMs. Few have been tailored to reflect the fact that many of the people who need support most don’t speak English and may not have a smartphone to interact with processing-heavy apps. Founders who can implement stripped down and accessible versions of their proprietary apps, or even just wrappers around foundation models that contain lots of legal information, news information and can scour the web for contacts, will be able to provide those most in need with some information when they may have none. The below ChatGPT reply is only helpful if you can access it. The bigger question is how to make sure that those who are most vulnerable don’t fall victim to misinformation or hallucination, as bad information can be worse than none at all.
Comment bots / Claim bots: I’ve written previously about how a group of crypto lawyer activists flooded the Treasury Department with over 100,000 comments that ultimately led the Treasury to delay provisions of a rule in accordance with the wishes of the activists. Automatically filing comments on federal rules seeking to roll back rights could well slow down implementation. Of course, you’ll probably think that empowering opposition parties is only good if you support the opposition, yet, it’s critical to realize that the channelling of opinions to government through technology is simply a form of democracy. Similarly, I’ve written about how systems like DoNotPay and and others have allowed me as an individual to challenge governments on items like parking tickets and challenge insurance companies who would normally have the upper hand in a claim. Automatic systems can be set up to facilitate the filing of claims with courts and regulatory bodies, which can provide some capability to individuals who might not be able to get a lawyer to take on their cause. Similarly, automated systems can trigger constituent letters to members of congress from those affected. All of these serve to amplify the voice of the individual but all have real trade-offs as well as they can further weaponize the legal system or at least create noise.
My broader point is that if these policy changes had happened ten or fifteen years ago, disadvantaged groups would have nowhere to turn but helpful lawyers willing to work for free. But today, technology can do a lot for them. And tomorrow it will do even more.
What did I miss?
—SW