CLERKING FOR THE LAST OF THE SILENT GENERATION
Jeff Gurley
A Gen Z clerk reflects on a year working with a judge shaped by Faulkner, Orwell, and nearly half a century on the federal bench.
I open chambers as Judge Jolly prefers.[1] After ensuring the doors are propped open—a signal to the other chambers we are open for business—I turn to his computer. As I log in, the program that opens is not Westlaw nor Outlook, but a streaming service called “Whispering Pianos Radio” that has been giving the court IT office headaches since before I was born. Judge pays several dollars a month for it. And he would proudly tell you it was the only thing he ever used the machine for.
His chambers, like any judge with nearly half a century on the bench, is filled with paraphernalia—gifts from former clerks, paintings, court photos, and, unique to him, a taxidermized raccoon. The walls are adorned with photos and paintings from his past. The only person I recognized at first was the president who nominated him, Ronald Reagan. Thankfully, I am now somewhat familiar with William Faulkner, though not as much as Judge would prefer.
I was born in 1997. My judge, in 1937. While I was raised during the information age, he grew up in small-town Mississippi during WWII and attended law school when tuition cost less than a decent pair of shoes. Literally—he once told me his little league football teammates didn’t have them.
I came in excited to contribute, fresh off a separate clerkship with a judge roughly my parents’ age—a jurist who had practiced at a major law firm as recently as 2019 and thus was fluent in modern technology. The difference was stark and immediate. Judge rarely sent emails and preferred dictating his thoughts for his judicial assistant to transcribe. No joke—there was a legit Dictaphone in my desk drawer.
He saw the world through the lens of slow-earned wisdom, layered with history and shaped by years of judicial discernment. In time, I adapted to his style—not seamlessly, but with increasing ease—finding a working cadence that respected his ritual rhythm.
Each day in chambers unfolded with rigid predictability. Chambers opened at the same time, closed at the same time, and Judge insisted on paper copies of everything. There were no email threads, no shared Westlaw folders, and certainly no Zoom meetings. He edited our paper drafts with a pencil and still dictated memos and emails to his judicial assistant. “Why would you need a machine to write something,” he once asked, eyebrows raised, “when you can just say it?”
To me, raised in the era of Google Docs, Slack, and AI co-pilots and having attended my first year of law school remotely due to COVID, the approach was a throwback. I tended to utilize web-based tools while drafting—not because I lacked the ability to write, but because I valued efficiency and flexibility. But in this chamber, the old ways prevailed—with good reason. Judge valued clarity over complexity and deliberation over immediacy. His workflow reflected that ethos.
The chambers ran like a well-oiled typewriter. Case packets were archived with rigidity. Memos were drafted with strict adherence to format and grammar. There was no tolerance for passive voice, rhetorical flourish, or ambiguous verbs. He had a particular distaste for the split infinitive (“required carefully to weigh” not “required to carefully weigh”). His editing pen was exacting. I learned to anticipate his cuts and, slowly, internalize his voice (think Benoit Blanc meets Frank Underwood).
Lunch breaks, too, were routine. Every Wednesday for several decades, he and his core group of friends met at 11:45. Like clockwork, his judicial assistant would send the “Wednesday luncheon email,” tally the numbers, and inform Judge whether quorum was met. Assuming a “Good Crowd!” the group met at the country club—the new location chosen by ballot after the prior location’s quality dropped. What I would give to be a fly on the wall at those lunches.
After our court issued a press release concerning AI, my co-clerk and I were tasked to explain it to him. And remember, his computer’s sole use was calming piano music. So, I showed him ChatGPT. At first, he was delighted. I prompted it to rewrite a recent Supreme Court opinion in his style. He laughed out loud.
Then came the shift. “How does it know that much about me?” he asked, leaning in toward the screen. “That’s not natural.” He wasn’t wrong to be unsettled. I explained how the models worked, how the technology didn’t really “know” anything but could predict patterns with astonishing fluency. He listened, fascinated, but his final verdict was delivered with characteristic wit: “So you’re saying I don’t need law clerks anymore?”
Whatever amount I knew about technology, Judge far surpassed that in judicial wisdom. He had an uncanny ability to get to the heart of a case. He could strip away procedural clutter and rhetorical excess until only the core issue—the essence—remained. He didn’t need bells, whistles, or hyperlinks. Just the briefs, the law, my unenlightened memos, and time to think.
When I mentioned how much law school costs today—over $70,000 a year—he was appalled. He paid a few hundred bucks a semester in the late 1960s and early 1970s. But that humility infused his judicial temperament. Nothing was taken for granted. The stories from his youth weren’t nostalgia. They were context. They helped me understand why he moved slowly, listened carefully, and wrote with exacting precision.
Early on, he had us read “Politics and the English Language,” George Orwell’s 1946 essay on clarity, precision, and the dangers of lazy prose. It wasn’t a casual suggestion. For Judge, good writing was good thinking. Orwell’s call to strip language of pretension aligned perfectly with his own judicial style. If I turned in a memo or draft bloated with jargon, I’d find the offending sentence circled with a margin note: “?”.
In turn, I learned to draft opinions not to impress but to inform. He taught me that the essence of the case is what really matters. For both Orwell and Judge, “if it is possible to cut a word out, always cut it out.”
As the last remaining Silent Generation jurists leave the bench, they take with them a deep reservoir of patience, professionalism, and principled restraint. These qualities are harder to quantify than citation counts or clerkship prestige and may be less flashy than the latest advances in AI, but they are essential to the dignity of the courts and the legal profession.
They also leave behind a warning: Speed is not wisdom, and technology cannot replace judgment. What I learned from Judge was not just how to be a better lawyer but how to be a steadier one. A quieter one. A more careful one. And when you think you know better than him, you’d better be prepared.
Although I may rely on new tools, I carry his voice with me. When I draft, I hear his edits. When I read a brief, I look for the essence. When I think I’ve written something clever, I ask whether it will stand the test of time.
I now find myself playing calming piano music as a reflex. I’ve modernized from Whispering Pianos—to a playlist on Apple Music streamed through noise-canceling headphones—but I’m reminded of the lessons Judge taught me each time it plays.
[1] Judge E. Grady Jolly serves on the United States Court of Appeals for the Fifth Circuit. He was nominated to the federal bench by President Ronald Reagan in 1982. A Mississippi Native, Judge Jolly was born in Louisville and graduated from the University of Mississippi (BA ’59, LLB ’62). Prior to his judicial appointment, Judge Jolly served as an AUSA for the Northern District of Mississippi, among other government positions, and ran a successful private practice in Jackson.
MEET THE AUTHOR
Jeff Gurley is currently a litigation associate in the Dallas office of Gibson, Dunn & Crutcher LLP. He previously served as a law clerk to the Honorable E. Grady Jolly of the United States Court of Appeals for the Fifth Circuit and to the Honorable Sean D. Jordan of the United States District Court for the Eastern District of Texas. He received his J.D. from the University of Michigan Law School and his B.A. from Washington University in St. Louis.