Hello, Darling Weirdo.
How do I write in a more engaging tone? How do I develop a voice? How do I stand out when AI can produce competent prose faster than it takes for you to get to the end of this sentence?
I got versions of
all of these questions in my inbox over the past few weeks. To find out, we're visiting a federal courthouse in Washington, DC.
Let's belly up to the bar.
* * *
Exhibit A:
"The President of the United States is the steward of the White House for future generations of First Families. He is not, however, the owner!" —US District Judge Richard Leon, ruling this week to halt construction of Trump's White House ballroom
Right away, what do you notice? The exclamation point, right?
There are 18 of them in a single
ruling. EIGHTEEN!!!
Judge Leon—a George W. Bush appointee, let the record show—is famous in legal circles for his punctuation. He used 26 exclamation points in an opinion last year blocking an executive order targeting the law firm WilmerHale. That ruling also included a gumbo recipe in a footnote. (It seems like I'm making up this recipe thing. I am not making it up.)
I saw his punctuation proclivity mentioned in a few places this week. But nobody interrogated it.
Court is now in session.
* * *
Legal writing is one of the most ruthlessly shackled genres in existence. The passive voice, the
bloodless construction, the deliberately neutralized tone. It is hereby ordered. The court finds.
Wide, jaw-cracking yawn. Legal writing veers into dullness like someone falling asleep at the wheel.
And yet I present as counter-evidence: Judge Leon, clearly feeling things and seeing no reason to pretend otherwise.
So. How do we write funnier? Develop a voice? Stand out?
The court calls its next witness... Generative AI, please take the stand!
The robot glides forward like a literate Roomba, bumping noisily up the stairs and into the witness box.
(There's a brief procedural snag when the bailiff holds out a Bible for the oath and realizes there are no hands.)
AI clears its nonexistent throat:
"I would edit Leon's rulings into oblivion," it confesses. "I would sand off the exclamation points. Cut the gumbo recipe." A nervous glance at the jury.
"I would produce something perfectly serviceable, utterly professional, and completely forgettable."
Low murmurs ripple through the gallery. A few boos rise from the back row.
Sustained.
* * *
The very things that make Judge Leon's writing memorable are exactly what a large language model would flag as unprofessional and scrub them out. AI prose can't violate expectation because it is expectation. It's the average of everything. There's nothing to bump up against.
Humor that makes a reader snort at their desk requires a self. A consistent enough presence that
the reader can feel when you depart from it.
That's why Judge Leon's exclamation points are funny: You expect a black-robed judge in a dead-serious tone like he's peering over his half-glasses at you. Instead, you get a guy who's absolutely had it.
The violation of that protocol has to feel intentional, not accidental. Unintentional weirdness is just
confusing. Intentional weirdness is earned. It signals a mind at work—which is what makes it delightful rather than disorienting.
Judge Leon doesn't accidentally deploy 18 exclamation points and a stew recipe. He knows exactly what he's doing. The exasperation is real, but the performance of it is deliberate—a wink at the reader, a sense of the person writing the words connecting with the person reading them.
The court calls it: That's judgment.
* * *
When speed becomes cheap, judgment carries a premium.
AI can produce competent prose in seconds.
What it cannot do is read a situation, weigh it, feel it, and leave evidence of that process on the page.
It cannot be the exclamation point in Judge Leon's literal judgment that says: I assessed this! I found it worthy of indignation! Here is my ruling! Try the gumbo!
That's the whole job for writers now.
Not information. Not even personality, exactly. Something greater:
Evidence of a mind behind the work.
So the path to standing out has never been more clear:
Stop editing yourself into acceptability. Stop covering up how your mind works.
* *
*
So where does that leave us?
‼️ VERDICT 1: Punctuation is a voice choice, not a grammar rule.
Most of us were trained to distrust the exclamation point—at worst, to hate its cheery, unhinged energy. The writer Elmore Leonard famously said never use one. Or else.
(Elmore didn't even add one exclamation point to that subtle threat. Bold.)
Judge Leon says pfft to Elmore and all that.
The lesson isn't "use more exclamation points." It's that every punctuation choice is a voice choice. (Rejoice!) (Sorry, couldn't help it.)
‼️ VERDICT
2: Feel the feels.
Professional writing norms push a neutral, balanced, measured tone. But readers feel something when a writer clearly feels something.
‼️ VERDICT 3: Constraints are powerful.
Leon operates inside one of the most formal, formatted genres in
existence. His exclamation points pop because of the surrounding formality. Know the conventions of your genre so you can break them.
‼️ VERDICT 4: A consistent quirk becomes a signature.
One exclamation point is a blip. Eighteen is a style. Commit fully to your weirdness. Do not lock yourself inside the prison of acceptability!
One more thing:
‼️ VERDICT 5: AI can extend your voice. It can't invent it.
AI can help you build on what's there. It can't discover what makes you, you.
And honestly: would you want it to discover your
weird for you? The fun is finding it yourself.
* * *
THE DISSENTING OPINION
A voice from the gallery pipes up: "But a judge can't get fired!"
The court acknowledges the
outburst. Bailiff, let them speak.
I hear you. Judge Leon has a job for life.
No performance review. No brand guidelines. No VP of Marketing who has Opinions and Thoughts about exclamation points or puns or whatever. Judge Leon can afford to be flamboyant in a way some of us can't.
But here's
where I'd push back.
You don't need to be Judge Leon, out there burning through legal-speak with a flaming punctuation mark.
You need to find the smallest version of that impulse your context will allow—and then commit to it consistently until it becomes the thing people recognize as yours.
A word you choose. A punctuation tic. A structural habit. Oddball metaphors. Some quirk that, over time, becomes a signature.
Judge Leon didn't start with 18 exclamation points. He started with one. Over time, it became his signature.
* * *
What is yours? And where is that line for you?
You know what I'm going to say, don't you...
You be the judge.
