How The Wall Street Journal’s AI Double Standard Undermines Its Perplexity Lawsuit

Allowing your outlets to use AI while you have a pending court case against an AI company is reckless and negligent. Quite frankly, it's a good way to lose your lawsuit.

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Billionaire, investor, philanthropist, and now a prime example of how a media company can lose a lawsuit. Wall Street Journal op-ed contributor Stanley Druckenmiller admitted this week he used AI for his latest column, titled “Let the Bond Market Speak,” which was published on Tuesday.

If you want to use AI, that’s fine — I don’t agree, but whatever you do, you boo-boo. However, when the company you’re writing for is suing an AI company for copyright infringement, this creates a very serious double standard that needs to be addressed.

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Let’s take a step back for a second. In 2024, News Corp., which owns the Journal, sued the AI company Perplexity for copyright infringement. According to a NewsNation report, News Corp. alleged, “Perplexity is illegally using the company’s copyrighted news content to feed search queries for its AI software.”

This lawsuit is ongoing and is currently in the “discovery” stage. Please note, “copyrighted news content” includes opinion columns.

How an AI-Written Column Comes Together

Here is exactly how Google AI Gemini says it creates a news column:

When writing a column, AI shifts from purely summarizing facts to building a structured argument guided by specific editorial instructions.

  1. Thesis and Stance Conditioning — A standard news model aims for neutral balance, but a column requires a point of view. The system receives a clear directive, either from a prompt or a style guide — for example, “Write an opinion column arguing why the city council should fund public transit over highway expansion.” This sets the target thesis that guides word selection.
  2. Adopting a Specific Persona (Voice and Tone) — Human columnists have recognizable writing styles. AI mimics this through system prompts and few-shot prompting. Tone settings instruct a specific voice — witty, authoritative, cynical, or conversational — while style matching has the model analyze sample articles from a specific writer or publication to replicate sentence structure, vocabulary choices, and rhetorical devices, such as rhetorical questions or anecdotes.
  3. Argumentative Structuring — Rather than using the “inverted pyramid” of straight news, the AI applies persuasive writing frameworks: a hook that opens with a vivid scene or surprising statistic, a counter-argument that addresses objections before refuting them, and a call to action that closes with a memorable takeaway.
  4. Context Grounding (RAG) — To anchor the column’s arguments in real-world facts rather than empty rhetoric, newsrooms use Retrieval-Augmented Generation. The AI retrieves live data, policy reports, or recent quotes to weave into its narrative.

The Prompt Behind the Column

This is the overarching problem for The Wall Street Journal and News Corp.

While we don’t know exactly what AI system Druckenmiller used to help amplify his lack of writing capability (I would love the irony if it was Perplexity), we do know that whatever system it was, it pulled its information from somewhere on the internet — not from Druckenmiller’s cabeza.

So, using the information we have at hand, the prompt Mr. Druckenmiller had to input into the AI system he used must have looked something like this: “AI, please create an op-ed article in the writing style of Stanley Druckenmiller criticizing Treasury Secretary Scott Bessent’s debt buyback plan.”

In order to get the “tone” of Druckenmiller, the AI would have had to analyze his style and use his previously copyrighted pieces to create a new one. This includes pieces he wrote and had published outside of The Wall Street Journal‘s purview. Thus, it’s reasonable to believe this piece, co-written by AI and Druckenmiller, likely infringed on someone else’s copyright.

News Corp. Can’t Have It Both Ways

News Corp. needs to get all of its writers on the same page. You cannot sue an AI company for copyright infringement and then also use AI to create your own content.

According to the New York Post (also owned by News Corp.), the Journal‘s editor, Paul Gigot, called AI “a fact of modern life. People will use it to assist in their work and their writing, including with research, checking grammar, editing, and more.”

Gigot later told his sister outlet, “The question for us is whether what we publish from contributors reflects an author’s original argument, and if the author has the standing and credibility to make it.”

Here is the problem, News Corp.: you cannot use AI only when it’s convenient for you. This article likely infringed on someone else’s copyright, since Druckenmiller has written for other outlets besides the Journal.

Allowing your outlets to use AI while you have a pending court case against an AI company is reckless and negligent. Quite frankly, it’s a good way to lose your lawsuit. And remember, President Donald Trump doesn’t like losers. Or in pop culture terms: happy AI games, and may the odds be ever in your favor.

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