Training data
Thomson Reuters wins out over ROSS. Plus a $25M drafting blunder, the prorogation hearing, and the SCC's new venture.
The best part of a Trump presidency is that every day feels like April Fools’ — is that headline real or satire?
Case in point: A Republican congressman just introduced a bill supporting Trump’s Greenland acquisition plan. There’s room for negotiation, but one thing is already certain — the proposed law mandates an official name change to Red, White, and Blueland.
Would they let us stick with “Canada” as the 51st state? TBD.
— Dylan Gibbs
TODAY'S DOCKET |
This week’s blockbuster AI lawsuit
An expensive drafting issue
Self-represented experts
Paddleboarding
Prorogation
Mediation

SPOTLIGHT 🔦
Don’t use Westlaw to train your AI

Step aside New York Times v. Open AI. If we’re deciding whether companies can lawfully train AI models on copyrighted data, legal tech deserves to set the precedent. And that’s exactly what this week had in store.
Thomson Reuters secured a victory against ROSS Intelligence on Tuesday, which could spell trouble for other AI systems trained on a diet of copyrighted content.
What happened? ROSS Intelligence tried to build ChatGPT for legal research before ChatGPT was a household name. Ask a plain-language legal question, get back a list of cases.
But their training data came from Thomson Reuters’ Westlaw — including proprietary headnotes and case classifications.
Using the headnotes, a team of lawyers created memos with good and bad answers to short legal questions. Some of the memos copied the headnotes word for word. And ROSS used those memos to train its AI model.
Thomson Reuters sued ROSS in 2020, alleging copyright infringement. The litigation was so expensive it shut ROSS down, but the corporation stuck around to defend the case and prove a point.
The ruling focused on a specific batch of around 2,800 headnotes and memos. For most (around 2,400), the judge said ROSS’s memos and the Westlaw headnotes were so similar that any reasonable jury would find ROSS copied the content. More importantly, at least for AI litigation watchers, he also rejected ROSS’s fair use defence.
Unfair use: Like the Canadian concept of fair dealing, US law allows some copying of protected material — depending on the nature of the material, how it was copied, and why.
ROSS argued its use of the headnotes was fair because it transformed the headnotes into something else. ROSS didn’t create its own headnotes — it created legal research software. The headnotes simply taught the software about the relationship between cases and rulings.
The judge saw it differently. Since Thomson Reuters uses its headnotes to help with legal research, and ROSS used them to create a competing legal research tool, there was no transformation.
When a user enters a legal question, Ross spits back relevant judicial opinions that have already been written. That process resembles how Westlaw uses headnotes and key numbers to return a list of cases with fitting headnotes…
Ross took the headnotes to make it easier to develop a competing legal research tool. So Ross’s use is not transformative.
Big picture: AI litigation is all the rage, with copyright holders aiming to hold AI companies accountable for ingesting their works and impacting their livelihoods. Here at home, CanLII sued Caseway for doing roughly the same thing as ROSS.
Many of those cases will turn on fair use and fair dealing, so the ROSS decision is great news for copyright holders. But other litigants might not get the same result — even if this judge’s reasoning stands. Take NYT v. OpenAI, for example. Compared to ROSS and Thomson Reuters, it’s much harder to see NYT and OpenAI as competitors.
I mean, feel free to ask ChatGPT for a recap of today’s events, but don’t expect the factually dubious slop you get back to replace award-winning journalism.

PRESENTED BY LEXSELECT
You didn’t go to law school to fight PDFs
You’re in the zone, drafting an argument that could turn the case. You copy a quote from a PDF, paste it into your brief and … it’s a disaster. A tangled mess of line breaks, odd spaces, and formatting errors.
You backspace, reformat, and try again. But every minute spent wrestling with bad formatting is a minute stolen from the work that truly matters for your clients.
That’s exactly why a seasoned litigator helped build LexSelect — the tool that lets you copy from PDFs with perfect formatting.
No mess. No wasted time. It can even add citations for you.
And for just a bit longer, LexSelect is free. This is your last chance to join the open beta before the product officially launches.
Try it for free today — your time is worth more than formatting work.

BY THE NUMBERS 📊
$2,500: The cost of paddleboarding too close to orcas. One woman learned that the hard way when footage of her wildlife encounter ended up on YouTube. She said didn’t know there was as legally-mandated buffer zone, but — as they say — ignorance of the law is no excuse.
If you fish, learn the regulations. If you hunt, learn the regulations. If you want to be around whales or other marine mammals, learn the regulations.
1.7%: The GDP Canada lost to increased government regulation from 2006 to 2021, according to a recent StatCan study. The booming regulatory landscape decreased business investment, pushed firms out of Canada, and stopped firms from entering.
$25 million: The missing bank account balance after (what looks like) a contract drafting blunder. The buyer in an M&A deal agreed to pay the seller a break fee if competition regulators rejected their proposed merger. At least, that was the condition discussed during the parties’ negotiations. But the contract was a bit more nuanced.
According to the terms, the buyer would only pay the break fee if the Canadian regulator rejected the deal, or if the deal failed during the first phase of the US regulatory process.
The US competition regulator blocked the deal, but it at least cleared the first phase of the process. As it turns out, nothing fails during the first phase — that’s not how it works.
The trial judge awarded the break fee, using the parties’ negotiations to shape her interpretation of the contract. But the Alberta Court of Appeal called that approach erroneous.
[The trial judge] erred in allowing evidence of the parties’ subjective intentions during negotiations to overwhelm the words of the Agreement.
Now the seller is stuck trying to get the $25 million from their ex-lawyers:
We are consulting our legal counsel and are considering our options including commencing an application for leave to appeal and continuing our claims against Canexus’s legal advisors on the transaction, and their insurers. We will continue to pursue all avenues of recovery available to us.

MAKING HEADLINES 🗞️
🧑⚖️ The Federal Court started hearing the prorogation challenge today and continues tomorrow. If you’re not up to speed, the applicants say the Prime Minister doesn’t have unfettered discretion to recommend prorogation. Since Trudeau’s decision to shut down government business was politically motivated, they say it wasn’t reasonably justified. The same argument succeeded in the UK during Boris Johnson’s Brexit era. If you’re interested in learning more, Paul Daly has some good blog posts about the issue. You can also live stream the Federal Court hearing by registering online.
🤝 The SCC might venture into mediation work, according to Chief Justice Richard Wagner during a recent podcast appearance. An interesting concept, but Court observers were a bit surprised by his comments on timing. Chief Justice Wagner suggested the Court could offer mediation in cases where leave to appeal is denied. Why would someone who won at every level of court want to renegotiate? The Court hasn’t offered clarification, except to say the idea is simply at the exploratory phase. They have a concept of a plan, if you will.
💊 Alberta wants the federal government to take a tougher stance on drugs or get out of the way. Premiere Danielle Smith takes issue with a 2020 directive telling prosecutors to divert drug cases away from criminal courts, and Bill C-5, which ended mandatory minimum sentences for drug offences. She said the federal government should scrap those laws or give the provinces jurisdiction over drug offences instead.
😔 Manitoba Crown prosecutors are struggling. According to a recent survey, two-thirds meet the criteria for PTSD, anxiety, or depression.
📚 Two UNB law students filed human rights complaints alleging that the school didn’t reasonably accommodate their disabilities.

THINGS NOT TO DO 😤
Don’t mix business and pleasure. The Law Society of Alberta is accusing a former Lethbridge Crown prosecutor of having an inappropriate relationship with a criminal complainant.
Don’t try to act as lawyer, party, and expert. An Ontario lawyer representing herself in a neighbour dispute tried to give expert evidence on construction vibration. The Court didn’t think she was qualified.
The Plaintiff has many years of experience in the legal field but, her practice has not been in construction… She has no formal schooling, training or industry certification for construction and/or engineering, or such other technical expertise normally required for certification by the Court. In addition, as a party, she cannot be an impartial witness. I note that she is the sole witness in her case.

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