The Ugly Truth About the NYT v. OpenAI Copyright Lawsuit
Content is About to Become Worthless… We Should All Cash in Now
Let’s talk about the copyright lawsuit that every AI founder, general counsel, and media is chain-smoking through their AirPods: New York Times v. OpenAI.
Everyone thinks the NYT is going to win. Legal Twitter’s hot take is that GPT regurgitates copyrighted articles too often, too cleanly, and too stupidly for OpenAI to squeeze out a fair use defense. The dominant forecast: big damages, bigger settlement, game over.
My prediction: they’re all wrong, OpenAI will win.
Don't be fooled by the headlines, no one is settling. And the NYT is going to lose.
If I’m right, you have a very narrow window — maybe 6 to 12 months — to sell your content to Big Tech before the courts tell them they don’t have to pay you a dime.
Because once this legal cloud lifts, so does your leverage. And your licensing value drops to zero.
Let’s break it down…
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📚 The Legal Consensus: NYT Has the Upper Hand
Here’s what most (smart but generic) lawyers believe right now:
OpenAI copied too blatantly. The Times filed receipts — actual side-by-sides showing GPT-4 spitting out near-verbatim paragraphs, including paywalled stuff. That’s the holy grail combo: access + substantial similarity.
It hurts the market. The NYT argues these outputs are replacing human readership. That’s a strike against fair use.
Bad venue for OpenAI. The Southern District of New York isn’t exactly Big Tech’s happy place. And the same district just held in Andersen v. Stability AI that output copying can absolutely nuke fair use.
So yeah, on paper? Looks bad for the AI labs.
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🧩 What OpenAI Will Say (and Why It Might Work)
Despite the bad PR, OpenAI’s legal playbook isn’t shabby:
Transformative use. They’ll argue that training an LLM is fundamentally different from reading — it’s more like teaching a machine to understand language, which qualifies as transformative under Google Books precedent.
It’s a glitch, not a feature. They’ll claim any regurgitation is a rare bug. No deliberate copying, no storage, no searchable database. Just statistical weirdness.
And — crucially — courts don’t like torching entire industries. Which brings me to the actual reason I think OpenAI (and Anthropic, and Meta, and all the other labs) will walk away clean on the training issue.
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🔥 My Contrarian (and Capitalist) Take: The AI Labs Will Win
I’m going against the grain here, but here’s the hard truth:
Training on copyrighted content will not be found to violate copyright law.
Here’s why:
Judges aren’t going to dismantle generative AI over how it learns. They’ll draw the line at how it outputs.
These systems are lossy. They hallucinate. And copyright law isn’t built for models that compress, remix, and resurface data probabilistically.
Once the case law settles, courts will likely split the baby: training ingestion = fair use; output copying = potential infringement.
That legal split is the endgame. And once we get there, your content archive becomes worthless.
Right now, you still have leverage — because Big Tech doesn’t know which way this will go. That uncertainty is your monetization window.
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💸 Own Content? You Should Be Licensing Right Now
If you have a clean, structured archive of written content, and you’re not already in licensing talks, you are missing what could be a six- (or seven-) figure opportunity that will absolutely not exist a year from now.
Who should be moving yesterday:
Mid-sized publishers with subscription archives or branded editorial voice (think: The Atlantic, Foreign Policy, Consumer Reports)
EdTech players: test prep, courseware, LMS platforms, corporate training content
Professional publishers: legal, finance, engineering, scientific, or medical verticals
Trade press and B2B: especially behind paywalls or with proprietary industry insights
Academic and think tank content: longform reports, whitepapers, policy analysis not widely indexed
What you need:
A coherent, structured body of IP (not a WordPress blog full of random posts)
Clean ownership — no messy freelancer agreements or unclear rights
A willingness to license quietly while the labs are still paying to hedge litigation risk
Most publishers don’t even realize this market exists.
Most of your competitors are sleeping through it.
If you wait to “see how the Times case goes,” you’ll miss the only window where your content is actually worth something.
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🪙 Why the AI Labs Are Still Paying (For Now)
Here’s the risk math that’s driving current deals:
Pay $250K–$2M now for a clean dataset = litigation hedge, good PR, and reduced risk of hostile discovery
vs.
Roll the dice, get sued later, and face 8- to 9-figure exposure plus a nasty SDNY precedent
As long as courts haven’t ruled, buying your dataset is a cheap insurance policy for Big Tech.
But when the courts say “training = fair use,” you’re no longer a risk to hedge. You’re just… indexed.
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❌ Don’t Wait for Justice. It’s Not Coming.
If your strategy is “let’s wait for the Times to win, then we sue too” — please know that this is the legal equivalent of holding out for an ex who’s clearly moved on.
The second that OpenAI wins this case — or settles in a way that signals legal confidence — Big Tech will shut down these deals. They won’t need your content anymore.
By the time you gear up to sue, there won’t be a budget left to settle with you.
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✅ What to Do Right Now
Inventory your IP — What content do you own, and what’s still locked in freelance hell?
Figure out your licensing story — Is your content niche? High-trust? Underrrepresented in training sets?
Get legal help — These deals are happening behind closed doors. Quietly. Strategically. Fast.
If you’re not in motion yet, you’re already behind.
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🎯 Bottom Line
This isn’t about whether you’re “right.” It’s about whether you still have leverage.
Right now — while the legal fog still exists — you do.
When the fog clears and the labs win? You don’t.
If you’re sitting on proprietary content and wondering what it’s worth to an AI lab, that’s the kind of strategic legal work I do. You’re running out of time to make the calls that still get picked up.
Let’s talk — before the window shuts.
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