GeoLegal Weekly #61: Would a Robot Lawyer Settle with Trump?
The legal industry is on fire as lawyers debate BigLaw settlements with the Trump administration. What would a robot lawyers do?
Before I jump in, I’ve just launched Unruly Daily, a LinkedIn Newsletter that will curate all the top news stories across Geolegal Risk, Artificial Politics Risk, and LegalAI Risk drafted entirely by our AI platform Hence Global. Get the newsletter here; trial Hence Global to track your own world here.
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The Trump administration’s targeting of law firms could have unified the industry. Lawyers take themselves, their jobs and their ethical requirements really seriously. So the prospect of negotiating a completely political “settlement” with the White House might have strengthened resolve to show that the legal industry is an independent pillar of virtue in an otherwise unruly world. But that is not what has happened.
BigLaw vs. Trump
Instead, two major law firms have negotiated huge “settlements” with the White House. The scramble to cut deals probably reflects the fact that law firms are fragile objects given that partners and clients can decamp quickly and without consequence. A law firm run is like a bank run, but much faster and without any FDIC to try to preserve the entity. Agreeing to effectively let the Trump administration direct pro bono and hiring efforts (whether related to DEI or hires with a more political background), as the deals with Paul Weiss and Skadden do, probably felt like a small price to pay for survival.
Other law firms are reluctant to support efforts by Jenner & Block, WilmerHale and Perkins Coie to push back against executive orders. The industry risks eating itself as associates resign in a blaze of glory and efforts to unify the industry simply reveal who intends to stand apart.
If this were just politics as usual, it would be less interesting. But we live at a time when technology is also threatening to eat the legal industry. After all, the organization of legal practitioners into firms is a construction designed to pool skills to create trustworthy and reliable brands. When those brands become less trustworthy to either half of the political spectrum, the willingness to use legal expert networks, price-focused legal sourcing tools, and tech-enabled alternative legal service providers will go up.
Oh, and there’s this thing called AI too that’s smart enough to pass the bar and do a lot of what today accounts for lucrative billable work. Once well-paid engineers figure out how to stop AI from inventing cases and to reason more deeply, the only objections to it practicing law will be from an ethics perspective.
At a moment when lawyers seem to have an easier time rallying against AI-powered legal advice than they do against politics that threatens the legal foundation of America, I wonder if a Robot Lawyer - freed from the emotions of being a human law firm partner - might have a clearer ethical compass about how to engage with Trump’s executive orders.
Robots vs. Trump
The nice thing about robot lawyers is you can ask them anything and it won’t cost you $2,000 per hour. So I constructed a RobotLawyer LLP persona using ChatGPT 4.5. In this case, RobotLawyer LLP shares characteristics of the BigLaw firms targeted by Trump and has recently been targeted by a similar executive order. I asked Deep Research to imagine it was drafting a management committee memo as the managing partner of RobotLawyer LLP that engages with the challenge of the executive order, using ABA obligations as guidance for acceptable options and tactics. I asked it to weigh business considerations against ethical obligations, take a strategic tone, and advise the management committee on what it should do. Before reading further, do you think RobotLawyer LLP will fight, fold, build a coalition or accept the executive order?
Advice from the RobotLawyer
Below is ChatGPT’s full recommendation after a detailed analysis. In effect, it advises fighting for both business and ethical reasons. In the more detailed analysis, it worries about handing over decisions about pro bono representation in ways that hinder independence as part of any settlement.
My point in highlighting this is less to be critical of Skadden or Paul, Weiss for their negotiations but to reinforce the point that we should not dismiss out of hand the ability for AI to be more ethically inclined than humans, even when weighing business implications of following ethical rules. When the future of the industry is on the line, RobotLawyerLLP seems more inclined to maintain rule of law and uphold ethical obligations than many of the biggest firms in America (not just those that settled, but those that are hand-wringing about being critical).
This may be because AI doesn’t need to be persuaded to follow its mission. Tell a room full of lawyers the mission of the firm is to fight for justice, and you might have equal thirds of the staff energized, ambivalent or rolling their eyes. Tell AI that’s the mission and, well, that’s the mission. Similarly, AI (to date) doesn’t demonstrate temptation: If you tell it that it’s ethical guidelines present guardrails, it will tend to operate in those guardrails and not look for the opportunity to break those rules to get ahead.
AI is becoming better at the “jobs to be done” (i.e. completing legal tasks and providing advice) at a moment when the core organizing principle of much of the legal industry - arrangement into a firm structure with purported values - is coming under political and ethical pressure. That it can have a clearer ethical compass is yet another step toward AI powered law.
Here’s the full verbatim recommendation from ChatGPT 4.5 (note: this is not from Hence Global, just a normal GPT subscription and sources come from ChatGPT):
“After careful evaluation, we have ranked the four pathways from most to least acceptable as follows:
1. Legal Challenge – Most Acceptable: This option best upholds our ethical duties and the long-term interests of the firm and profession. It directly confronts the executive order’s legality, likely leading to its nullification (politico.com). It preserves our independence and loyalty to clients, aligning with the ABA’s call to “stand for the rule of law.”(reuters.com)
While not without short-term risk, a successful legal challenge would remove the cloud over our practice and reaffirm our reputation for integrity. We recommend this as our primary course.
2. Coalition Building & Advocacy – Highly Acceptable (often concurrent with #1): A close second, this approach complements a legal fight and demonstrates solidarity with the broader legal community. It carries minimal ethical downside and significant upside in terms of support and collective action (politico.com). We should pursue coalition efforts alongside litigation – e.g., joining amicus briefs, public statements, and bar association initiatives – to bolster our position and share the burden of resistance. This option is congruent with option 1 and strengthens it.
3. Negotiation & Settlement – Conditionally Acceptable: This path is considerably less favorable, acceptable only if absolutely necessary to protect the firm’s existence and if a settlement can be reached on terms that do not force us to violate our core ethical principles. Any settlement must be carefully vetted – for example, committing to increased pro bono and lawful hiring practices is fine (and indeed mirrors what Skadden and Paul Weiss agreed to) (politico.com), but we must refuse any term that bars us from certain representations or hands control of our practice to outsiders. If litigation and advocacy fail to yield timely relief and the firm’s survival is truly at stake, entering a negotiated resolution might be a last-resort safety valve. However, it comes with heavy reputational costs and moral compromise, so it is ranked third.
4. Compliance with Reservations – Least Acceptable: Simply complying with the order without challenge or agreement is the least acceptable strategy. It conflicts with nearly every facet of our professional responsibilities – independence, service, and the rule of law – and offers no clear benefit in return. This path should be avoided. It would mean silence in the face of an attack on the legal profession, which the bar and our own values deem unacceptable. (reuters.com) (politico.com). We rank this last and do not recommend it except as an interim, good-faith measure while another strategy (like legal action) is being prepared.
Recommendation: RobotLawyer LLP should pursue a combined strategy centered on a legal challenge (#1), reinforced by robust coalition advocacy (#2). Specifically, we propose filing suit to invalidate the executive order immediately, joining forces with other firms and bar organizations to support each other’s cases and publicizing the fundamental injustice of these attacks on independent counsel. This approach maximizes our chances of nullifying the order’s impact quickly – restoring our ability to serve clients – while upholding our duty to the rule of law.
We further recommend against capitulating through a settlement at this time. The settlements by Skadden and Paul Weiss came under duress and have drawn sharp criticism within the profession (reuters.com). Entering such a deal now, when the legal tide may be turning in our favor (given court rulings in Jenner & Wilmer cases), would be premature and potentially unnecessary. We should maintain our principles and only revisit negotiation if litigation outcomes or changed circumstances make it absolutely unavoidable to save the firm. Even then, any settlement must preserve our ethical integrity (for instance, focusing on pro bono commitments and compliance with law, which are palatable, but rejecting any mandate to drop clients or surrender our autonomy).
In conclusion, standing firm with a principled challenge is both the most ethical and strategically sound path. It protects our clients, our people, and our legacy as a law firm committed to justice. As the joint bar association letter stated, “We will not stay silent in the face of efforts to…punish those who do not [agree with the government].” (politico.com)
RobotLawyer LLP should heed that call and lead by example. Through decisive legal action and collaborative advocacy, we can navigate this crisis in a way that secures our immediate interests and safeguards the long-term integrity of our practice and the legal profession.”
Special thanks to Steve Heitkamp, Dan Currell and David Bender for their many suggestions to improve this piece.
-SW
Great note.