They say you are not supposed to meet your heroes. The reasoning goes that the person rarely matches your idealized version of them, and the experience can only disappoint. Nothing could be further from the truth. Not long after finishing law school, I found myself unemployed and living in a new city, having followed my wife when she relocated for work. I spent that summer applying for jobs and anxiously waiting for her to come home each evening. At the time, it felt like torture. All those years of work, and now this—it left me with a profound sense of being unmoored.
As my 30th birthday approached, my wife suggested we spend a weekend in Boston to take my mind off the fruitless job search. I agreed. We wandered around Newbury Street, popping in and out of stores. As I stood admiring an overpriced sweater I couldn’t afford, in walked David McCullough.
I may be dating myself—or at least revealing my nerdy proclivities— but McCullough was one of the most celebrated non-fiction writers of the late 20th and early 21st centuries. A bestselling author and two-time Pulitzer Prize winner, he wrote definitive biographies of Harry Truman and John Adams. He was also a gifted speaker with a commanding voice, lending his talents to Ken Burns’ legendary Civil War series and narrating the Academy Award-nominated “Seabiscuit.”
With a shock of white hair and always dressed as if en route to a Nantucket cocktail party, McCullough embodied success and distinction to me—a writer whose work broke through the culture so thoroughly that he is widely credited with rehabilitating the reputations of both Truman and Adams.
My eyes went wide. I started tugging at my wife’s sleeve, whispering who had just walked in. She knew him well, having endured years of my enthusiasm. She also knew of our personal connection— we’re both from Pittsburgh and graduated from the same high school. She encouraged me to go say hello. I looked at her like she was crazy. She nudged me anyway, and I mustered the courage to approach without looking like a stalker. “Mr. McCullough,” I said, “I just wanted to say I’m a big fan. I’m also from Pittsburgh—I went to Shady Side Academy.” McCullough, accompanied by his equally elegant wife Rosalee, smiled warmly. “A fellow Pittsburgher. What year did you graduate?” We exchanged pleasantries for a few minutes about Western Pennsylvania and how often he got back. He asked what I did for a living. I told him I was a lawyer who had recently relocated to Boston but hadn’t landed a job yet. “It’s a tough market,” he said. We exchanged a few more kind words, and I thanked him for his time, conscious of not overstaying my welcome. As my wife and I turned to leave, McCullough called after me: “Don’t worry. Everything is going to work out fine.” I was elated. About a month later, I landed my first interview— and got the job. My legal career in Massachusetts was underway.
AI and the Coming (Or Already Here) Revolution
We, as a society and a profession, are inundated with stories about the world’s imminent demise at the hands of AI. As usual, our profession feels like it is lagging—or worse, ignoring reality.
But AI is not new. These concepts have been percolating for decades. What has changed is the quality of the systems now publicly available. I’ll spare you the specific names; you know them all. I do not think it is an overstatement to say these tools have the potential to significantly upend the way we practice law. Specifically, the tiered structure of Big Law—and the relegation of mid-size and small firms to a lesser rung on the prestige ladder—may be on the precipice of extinction, if we want it to be.
Before you assume I am calling for a “Workers of the World Unite” moment, I am not. I am, however, questioning why the legal caste system—derived in large part from elite law schools and the larger corporate and tech-centric firms that hire from those institutions—gets to drive the AI conversation for the entirety of the profession. What claims and defense professionals should be asking is: Isn’t it time for a change?
In typical lawyer fashion, let’s start with the negatives. In about five minutes of doom scrolling on LinkedIn—guilty— you will find countless posts about lawyers who have been reprimanded or sanctioned by courts for submitting work product containing AI-generated case citations that do not exist: AI hallucinations, as they’re called. One of the pitfalls of the current AI landscape is that some systems are effectively designed to tell the user what they want to hear. It is essentially a first-year associate who does all the hard work but lacks the fundamental judgment to say, “Maybe it’s not a great idea to make up case citations before turning in this draft to the supervising attorney.”
Despite some of the most expensive and well-heeled firms boasting about the robustness of their AI policies, they tend to be the same firms grabbing headlines for these citation debacles. The bottom line: It is bad practice, and there is no excuse for failing to verify a case citation. But this is not a reason to ignore the remarkable capabilities of these tools. It is like saying the risk of speeding should discourage you from driving altogether.
More to the point, I saw a recent post from a senior lawyer complaining about having to rewrite a young associate’s AI generated, mistake-riddled brief. The post reeked of the same arrogant complaints senior lawyers have raised about junior lawyers for decades: sloppy, not well thought out, lazy. I would hesitate before laying all the blame on the young lawyer. Maybe the problem is the model lawyers adopted from Paul Cravath at the end of the 19th century, when the senior/junior attorney mentoring relationship was born. This model is not purely altruistic, as much as senior lawyers tell themselves it is. It is, in part, built on the senior attorney’s reluctance to do the yeoman’s work on a case once they reach a title with a “P” in front of it.
This is exactly why we should be paying more attention to AI, which offers a bridge, but only for those willing to cross it. Nothing should replace the proper training of new lawyers: Good, patient writing helps refine and revise bad thinking, and that’s foundational. But perhaps what the partner should have asked is: How could I have used this AI system to produce a more effective brief myself?
Ripple Effects
Small to mid-size firms have always struggled to match the resources, time, and output quality of Big Law. The well-credentialed and well-compensated have cornered the market on superior work product for a long time. That is not to say solo practitioners and mid-size firms cannot compete—they can, they have, and they will—but it is hard, and resources are often stretched dangerously thin at rates far below those of their corporate counterparts.
Proper use of AI tools can close that gap to the point where you would not know whether the author graduated first in her class at Yale or at the bottom of his class at a school not mentioned in any magazine. That is how far the technology has come, and it is only going to improve from here.
It is not only legal briefs; everything is changing. Extensive medical record reviews can be completed in seconds. Deposition summaries, likewise. Analytical case forecasting? The percentages we have been offering clients for years about their chances at trial might finally be based on real data and not just trial-attorney bravado and war stories.
This raises the question: Why should a client pay $1,000 an hour to an attorney when they can get comparable work product at a fraction of the cost? Big Law will tell you it is the education, the experience, the relationships, and the expertise. We know it when we see it—the prestigious schools, the fancy titles, and the former titles: Ex-This and Ex-That. That is the equivalent pretentiousness of George Costanza using the headshot of Elaine’s model friend to gain access to the secret beautiful-people world in “Seinfeld.” We understand. We’re elite. We know better
At least for the time being, that argument appears to be holding. The upper echelons of the legal caste system are dictating the future of the profession as it grapples with the AI onslaught. But how long will it last? How long should it last? It does not take a fancy law degree—which I do not possess—to recognize that businesses and insurers could completely retool the way claims and contracts are handled. Firms that have, frankly, been overcharging for years are going to find it increasingly difficult to justify doing so.
On the more troubling issue of privilege—whether inputs into publicly available AI systems are protected—the early results are mixed and concerning. A recent ruling out of the Southern District of New York, United States v. Heppner, held that information entered into a public AI system could not be considered privileged, as the court determined that doing so treated the AI platform as a “third party,” effectively waiving confidentiality. To call this controversial would be an understatement, and there are already decisions that conflict with the Southern District’s reasoning.
The decision is nonetheless a harbinger of what will come: a fractured judiciary on the question of AI’s role in the legal profession and how far privilege can extend into its use. The court relied heavily on the concept that public AI platforms are just that—public—and that there can be no reasonable expectation of privacy. In theory, that logic holds. In practice, ascertaining what can and cannot be discovered through these systems is genuinely hard. The protection of confidential and privileged data is a real and ongoing issue, but it is a solvable one.
Publicly available LLMs can offer confidentiality protections, generally through enterprise licenses. Legal specific companies are emerging daily with products making similar promises. The potential pitfalls are real—but they are not sufficient reason to ignore AI platforms or broadly chastise them on LinkedIn. These tools are here. They are not going away. Failing to get adequate training on them, out of fear of confidentiality concerns or otherwise, would leave lawyers—all lawyers— woefully unprepared for what’s coming.
A Fine Ending
Fast forward two years. My high school hosted an alumni event in Boston. These gatherings always carried a quiet anticipation over whether McCullough would appear. Now gainfully employed, I attended without any particular expectation—I had already met my hero.
To everyone’s surprise, he was there, surrounded by middle-aged history enthusiasts as though he were one of The Beatles. I hung back, content with the memory I already had. As the event wound down, I slipped toward the exit.
As the elevator doors were closing, a hand jutted in—and there was McCullough, escorted by one of the school’s representatives, his wife beside him. He smiled, glanced at my name tag, and graciously introduced himself. I mentioned that we had actually met a few years earlier, on Newbury Street. He nodded and asked what kind of law I practiced. When the elevator reached the ground floor, he made his way toward the exit—but paused, turned back, and looked at me. “I told you everything was going to work out fine.” He smiled, gave a wink, and was gone.
My encounter with David McCullough is about as far from AI as you can get—and yet his advice is not. I was fortunate enough to meet one of my heroes at a moment when I desperately needed a kind word. And I think that is exactly how we should approach this professional moment. The news feels relentless, and rapid technological change is not making it any easier. But if we meet this moment with thoughtful preparation, honest acceptance, and a measure of strategy, I am confident that everything is going to work out fine.