Remarks of Judge Richard J. Sullivan on receiving the 2026 Weinfeld Award

Remarks of Judge Richard J. Sullivan

Weinfeld Award Honoree Acceptance Speech

October 20, 2026

 

Introduction

Thank you, Judge Gonzalez, for that incredibly generous and kind introduction. As Judge Gonzalez mentioned, we have known each other for over thirty years, dating back to when we joined the US Attorney’s Office in Manhattan as General Crimes Assistants in 1994. During the intervening three decades, Judge Gonzalez has distinguished himself as a superb trial lawyer, and now as a superb district court judge in the Eastern District of New York. When we were in the Office together, I made a point of going to watch his opening statements and summations, since he was generally regarded as one of the very top trial lawyers there. But I can honestly say that the introduction he just gave was probably the best opening statement he’s ever given. I have to assume that’s attributable to me; I’m happy to be his muse.

Seriously, I want to thank Judge Gonzalez for an introduction that made me blush. I also want to acknowledge Scott Klugman, who has organized the Weinfeld Luncheon for as long as I can remember. Scott and his firm, Levine Lee – along with NYCLA’s Executive Director, Sophia Gianacoplos, and the rest of the NYCLA team, including Azelia Cutts – have once again put together a wonderful event here at the Museum of Jewish Heritage. The Weinfeld Luncheon is always one of the highlights of the Fall, and while they make it look easy, the fact remains that a tremendous amount of effort goes into organizing and planning this event. So please join me in a round of applause for Scott, Sophia, Azelia, and the many others who have worked tirelessly to make this such a fantastic event, down to the very last detail

The Long Shadow of Edward Weinfeld

It is truly an honor to receive award named after the great Edward Weinfeld. Judge Weinfeld is to district judges what George Washington is to Presidents; what John Marshall is to Supreme Court Justices; what Learned Hand is to Circuit Judges; and what Judge Judy is to . . . television judges

Edward Weinfeld is the gold standard of judging; he is the model to which all judges aspire and the yardstick by which all judges are measured.

I never had the pleasure of knowing Judge Weinfeld or even appearing before him. Judge Weinfeld died in January 1988, when I was a first-year law student. But I remember his passing, because my mother sent me his obituary from the New York Times. My mother wasn’t a lawyer; she went to work right after high school and never went to college. But she was smart and savvy and an avid reader of the New York Times. The obituary struck her as a significant moment – the passing of a renowned jurist – and while I don’t think she ever fully knew the difference between a federal judge and a state judge, she thought I should be aware of Judge Weinfeld and what he stood for. She was right.

Of course, at that point in my legal education, my knowledge of the district court was hardly more sophisticated than my mother’s. With barely a semester of law school under my belt, I’m not sure I’d even read a district court opinion, much less understood the enormous impact that a district judge can have in a particular case and on the course of justice. Still, I recall being impressed by that obituary, which described Edward Weinfeld as “one of the nation’s most respected federal judges” who was “known for dedication and fairness of such a high order that he became a legend in legal circles.” It stuck with me. And in fact, I still have it (along with every other letter my mother ever wrote me).

My initial impression of Judge Weinfeld deepened over time, as I encountered his former law clerks in the early years of my career. It was at Wachtell Lipton Rosen & Katz, where I began my career as an associate, that I first met Marty Lipton and Paul Vizcarrando, each of whom had clerked for Judge Weinfeld decades earlier. I saw firsthand their tireless work ethic and their commitment to excellence – qualities which they in turn had learned from Edward Weinfeld. As Marty once said in describing his clerkship: “Good was never good enough; great was never great enough. Perfect was the goal.” I learned that perfection was expected always, even at three o’clock in the morning. I didn’t learn that in law school; I learned it at Wachtell Lipton. Only later did I realize that this was the standard set by Judge Edward Weinfeld.

After a few years in private practice, I joined the US Attorney’s Office as a prosecutor. There I met Mark Pomerantz, another Weinfeld clerk, who was then the Chief of the Criminal Division. He too insisted on the Weinfeld standard of perfection. But he also stressed that excellence must always be pursued in the service of justice and fairness.

It was during my time at the US Attorney’s Office that I first met John Koeltl, then a newly minted district judge who had also been a Weinfeld clerk. I remember appearing in front of Judge Koeltl and making the mistake of thanking him for some minor courtesy that he had shown me in court. I recall him putting up his hands as if to say “stop,” while he gently admonished me to “never thank the Court.” I later learned that this was pure Weinfeld.

I recall another occasion when, as a gung-ho narcotics prosecutor, I brought Judge Koeltl a wiretap request while he was on criminal duty, in what is colloquially known as “Part One.” I remember dropping off a stack of documents that was nearly two feet high, including the wiretap application, assorted affidavits, and proposed orders to the law enforcement agencies conducting the investigation and to the phone company. A lot of these materials were statutory boilerplate, but the inquiry was ultimately a fact-intensive and case-specific one in which the government was required to establish probable cause that the phone in question was being used to facilitate specified federal crimes and that there was no less intrusive means to obtain the evidence than the requested wiretap. I remember that Judge Koeltl had read every line of every page; I also remember that he uncovered two typos in the hundreds of pages of materials I’d submitted. They weren’t substantive, so they didn’t affect the application or orders, which the Judge signed. But I recall being embarrassed. Perfection was the standard at Wachtell Lipton; it was the standard at the US Attorney’s Office; it was the standard for Judge Koeltl; and it was, of course, the standard for Judge Weinfeld. It never happened again.

The Book

When I became a judge in 2007, my appreciation for Judge Weinfeld rose to a different and higher level.

I had been a judge for just a few hours when the Clerk’s Office put me in temporary chambers at 500 Pearl Street. This was before I had clerks; before I even had a robe. My temporary chambers were empty, save for some scattered F. Supps in the half empty bookcases and a thin bound volume that was the lone book on an otherwise bare coffee table. The book – this book – was a monograph entitled “Edward Weinfeld: A Judicious Life.” It was published on the tenth anniversary of the Judge’s death by the Federal Bar Foundation. (Can I even say “Federal Bar Foundation” at a NYCLA event? Let’s just say “a lesser bar association,” so we offend no one.) The book was prepared by the Judge’s former colleagues, his former clerks, and his family, and it included remarks about his approach to judging by the Judge himself and those who knew him best – including his granddaughter, Amy Weinfeld Schulman, who is here today.

I’m not sure how the book got there. I don’t know if it was intended for me specifically or merely left over from a prior tenant. But it was, and continues to be, a primer on how to be a judge in the tradition of Edward Weinfeld. That book has followed me to every new chambers I’ve had over the past twenty years. It still sits on the coffee table in my current chambers, though it has become slightly faded from the sunlight that shines on it in the early morning hours. It’s a book I still peruse to this day, to the point that certain parts of it are now committed to memory.

The List

The Book probably offers the best insight into Edward Weinfeld and his approach to judging. But I have gained additional insights on that subject by attending this luncheon every year for the past two decades. Each year, I have learned a little more about Edward Weinfeld – from the stories and anecdotes recounted by the speakers, and from the careers and example of those selected to receive the Award. Those recipients, not surprisingly, share many of the Judge’s greatest qualities.

Many of those past recipients are here today. And some of them are now my colleagues on the Second Circuit, including Jon Newman, Pierre Leval, Jerry Lynch, Denny Chin, Dennis Jacobs, the late Robert Katzmann, Reena Raggi, and last year’s recipient, Debra Livingston. Others are giants of the district court, which would probably have pleased Judge Weinfeld most, including John Koeltl, Loretta Preska, Carol Amon, and John Keenan, who passed away two years ago and remains the finest district judge that I have ever known personally.

What Made Weinfeld Great

During Judge Weinfeld’s rookie year on the SDNY bench, another rookie took this City by storm. That was Willie Mays, then playing uptown at the Polo Grounds for the New York Giants. Mays’ manager, Leo Durocher, once described Mays as a “five-tool player” who could hit for average, hit for power, run, catch, and throw. Mays excelled in each aspect of the game, and for Durocher’s money, Mays was the best player ever to wear a uniform. My father was a Brooklyn Dodgers fan – he certainly wasn’t a Giants fan – but even he agreed that Mays was the best ballplayer he ever saw.

In a sense, Edward Weinfeld is the judicial equivalent of Willie Mays

(By the way, I should mention that this analogy would have been completely lost on Judge Weinfeld, who didn’t spend much time reading the sports pages. In fact, Judge Weinfeld once had a case in which Mickey Mantle had been subpoenaed as a witness, and when Mantle’s lawyers requested an adjournment of the deposition so he could go to Spring Training, Weinfeld reportedly inquired: “Who is Mickey Mantle” and “What is Spring Training.”)

But if you’ll indulge me in the metaphor, I think it could be said that Weinfeld was a “five-tool” judge. He was smart, he had superb judgment (and we all know that intelligence and judgment are not the same thing), he was decisive, he was an excellent communicator (both orally and in writing), and he was fair. Add to that an encyclopedic knowledge of the law, tremendous organizational skills, and a prodigious work ethic, and I think one could say – as Durocher did of Mays – that Judge Weinfeld was the Greatest of All Time.

A Man, Not a Machine

The stories one hears about Judge Weinfeld often focus on his remarkable work ethic. He routinely arrived in chambers by 6:00 am or even earlier. He typically worked seven days a week, including holidays. He rarely took a vacation. He never took senior status, remaining an active judge until his death. He presided over his final trial in the district court almost until his last breath at age 87.

In recounting his capacity for work, someone once described Judge Weinfeld as a “machine.” But he was not a machine. And what made him a great judge were not his machine-like qualities. What made him great was his humanity. And I think that’s worth reflecting on.

We live in an age in which, for the first time in history, being human is viewed as a mark of inferiority. The Greeks had a different view. As Sophocles wrote in Antigone, “Numberless are the world’s wonders, but none is more wonderful than man.” Through intellect and reason, through courage and creativity, man could master the seas with his ships; subdue the land with his plow; tame wild beasts and fish and birds to submit to his will; deflect the arrows of snow, rain, and wind to make himself warm and secure. Sophocles described man’s intelligence as a “force beyond all measure.” And man’s greatest invention, according to Sophocles, was the law. “When the laws are kept, how proudly his city stands!”

For millennia, that was the accepted view. But that is no longer the case. With the rise of supercomputers, algorithms, large-language models, and AI, we have come to question man’s relationship with his own inventions, which seem to have eclipsed the inventor and made him seem puny and frail. Even Judge Weinfeld’s remarkable stamina and drive are no match for these new machines, which have no need for rest or nourishment or diversion. Weinfeld’s encyclopedic knowledge of the law can now be surpassed by a second-year law student with a Lexus password. His organizational skills now seem almost quaint. Judge Weinfeld kept a copy of every opinion he ever wrote, in a three-ring binder, with each opinion numbered, and he referred to them frequently. I too keep a copy of every opinion I’ve ever written. Not a hard copy, of course; no, I keep a digital binder, which I call “Westlaw.” These and other digital tools make even the most ordinary judge the organizational equivalent of Weinfeld.

AI has the capacity to transform human activity far beyond mere mechanical devices like the plow or assembly line. AI can now fashion an opinion that sounds more like Weinfeld than Weinfeld. And it has caused some to wonder whether judges, and the law itself, will ultimately be replaced by machines.

Maybe they will, but I don’t think so.

The Humanity of Edward Weinfeld

I have no doubt that Judge Weinfeld would have adapted to new technologies. I expect he would have welcomed additional law clerks and word processing and legal search engines and maybe even AI itself. I suspect he would have seen them as tools that could make him more efficient and even more effective as a judge.

But what made Weinfeld truly exceptional were his human qualities – traits of character that no machine can replicate. As I reflect on Judge Weinfeld’s life and legacy, I think those traits boil down to five: Judgment. Care. Patriotism. Joy. And Love.

Judgment

The act of judging is ultimately about judgment. Judgment is defined as “the mental ability to understand something, form an opinion, and reach a decision.” A machine can’t exercise judgment. Oh, I know that AI can spit out an answer to a question that synthesizes the universe of decisions on a given topic. And there may even be some who choose – if not now, perhaps one day soon – to submit to an AI arbitrator as a sufficient and cheap way to resolve disputes.

But the best judges, like Weinfeld, have always recognized that judicial decision-making – the exercise of judgment – is a uniquely human activity. AI can bang out facts and prose; but it can’t dispense justice.

Judgment is crucial to judging, and Weinfeld had it in spades. But judgment is not exclusively the province of judges. Lawyers and juries too are expected to exercise judgment. Our system of justice depends on it.

Caring

In addition to exercising judgment, Weinfeld also reflected another uniquely human trait – the capacity to care. Weinfeld’s hours were not kept for their own sake. He worked as hard as he did because he cared deeply about the litigants and the institution that he served.

That capacity to care also distinguishes us from machines, and it’s perhaps the greatest part of Edward Weinfeld’s legacy. What drove him to read every submission, to consider every argument, to listen to every lawyer and litigant, to carefully weigh and balance every decision was his conviction that every case – and every litigant – mattered.

And it was not just the outcomes that mattered. What was often more important than the actual outcome of a case was that the litigants left the courthouse understanding, if nothing else, that they had received a fair hearing and been respected in the process. The process itself had to be thoughtful and careful and human.

When I first became a judge in 2007, Judge Charlie Brieant – by then a senior judge who had himself received the Weinfeld Award a few months earlier – told me something that I’ve never forgotten. He said: “Always remember that everything you say and do on the bench, and every word you issue in an order or opinion, has the potential to enhance or diminish the reputation of this Court.”

Weinfeld understood that. And it’s why he took his job so seriously. He knew that litigants, large and small, expected a process that was deeply human. They expected a judge who was not just wise and not just fair; they expected a judge who cared.

That capacity to care defines us as human beings. And it’s a quality not limited to judges. In the Weinfeld book, the judge’s granddaughter – Amy Schulman, who is here today – recounted a conversation she had with her grandfather shortly before he died, when she was a law student. And from that conversation she came to a profound realization: that “Edward Weinfeld was convinced that there was nothing magical about being a good lawyer or judge. All that was required was hard work, a conscience, and the capacity to care – really care – about what you were doing.” I think she was right about that. And I know that her grandfather would be very proud of the lawyer she became and the career she has had.

People sometimes ask me what I look for in law clerks. And there’s no real mystery to the answer. I basically look for clerks who have the five tools I mentioned before – intelligence, judgment, decisiveness, writing ability, and fairness; those are the qualities that will land someone an interview. But what I’m really looking for, ultimately, are people who care as much as Weinfeld did. I want clerks who will give their cases their full attention, even though their names will never go on the opinion.

Joy

To care deeply requires tremendous effort on the part of judges and lawyers. But perhaps paradoxically, that effort was not a burden to Edward Weinfeld. He derived joy from the experience. The way an artist feels about his paintings, the way a poet feels about his words, the way a philosopher feels in contemplation, that’s how Edward Weinfeld felt about judging.

My former law clerk Spencer Furey, who is here today, got me a framed quote from Weinfeld that I keep near me in chambers. Here’s what it says.

“Now and then, a well-meaning friend, concerned that perhaps I am overworking, suggests that I take it easy. My response is simple. I explain that when, at a fairly early hour of the morning, I put the key into the door of my darkened chambers, switch on my lights and walk across the room to start the day’s activities, I do so with the same enthusiasm and excitement that was mine the very first day of my judicial career. I tell my concerned friends that what one enjoys is not work but rather joy; the immense satisfaction that one is privileged to play a daily role in that noblest of callings, which is the rendition of justice.”

I know that feeling – the thrill that comes from entering chambers and having the privilege to work on matters of importance in the interest of justice. I often feel it on Sunday mornings. My family and I go to the 8:00 a.m. Mass, and after that I come to the courthouse, flip on the lights in my empty chambers, and then spend several hours alone doing something I love.

My hope is that every judge, and every lawyer, is able to know that feeling of joy that comes from doing meaningful work. That’s something that a machine can’t know. And it’s a feeling that’s more powerful than money or fame.

Patriotism

I think the joy Weinfeld experienced in judging derived at least in part from the noble purpose of the work. Edward Weinfeld was a federal judge. He was a judicial officer under the Constitution and laws of the United States. He viewed that calling – and that Constitution – as noble and good. He was a patriot. And patriotism is another human trait that a machine can’t comprehend or duplicate.

This summer we celebrated the 250th anniversary of the Declaration of Independence. As we reflect on those words, we have an obligation to recognize, as Weinfeld did, the unique history of our country. And it’s fitting that we do so here, in this museum, within sight of the Statue of Liberty.

Edward Weinfeld was the son of Jewish immigrants, and he clearly understood the promise of this Nation under the Declaration, the Constitution, and the Bill of Rights. His parents – like my grandparents – sailed past that statue as they began their American story. They weren’t naïve; they weren’t delusional. They recognized clearly and objectively that this country offered them more than what they could have hoped for in their native land. Like countless immigrants before and after them, they understood the promise of liberty and the opportunity represented by that statue and our founding documents.

That statue and those founding documents make me think of Judge Gonzalez, who came to this country as a small boy from Cuba, his parents determined to give him a life they could not have imagined had he remained there. My father-in-law and mother-in-law did the same for my wife and her sisters. In this building, I think of the millions of Jewish immigrants – before and after the horrors of the Holocaust – who came to this country understanding it to be a force for good and a beacon representing the rule of law and the dignity of the individual.

In my chambers I have a small black and white photograph that was given to me by my former law clerk, Andrew Lief. In the photo is a large Jewish family, including his grandfather, then about 10-years old, in happier times. Within a few years of that photo, the entire family – including seven children – would be taken to concentration camps. All would perish, except Andrew’s grandfather. After surviving the camps, Andrew’s grandfather came to the United States as a young man. He sailed past that statue. And he believed deeply in the promise of America and the rule of law that defines it.

This year we commemorate the 80th anniversary of the Nuremberg trials. Those trials represent a uniquely American view that the rule of law has a place in the affairs of nations. Edward Weinfeld understood as much, and he recognized that America’s founding documents and institutions of justice could be a beacon for a broken world. We too should embrace that love of country that he modeled.

Every lawyer in this room has taken an oath to support and defend the Constitution and laws of the United States. Think about that. Not every profession has an oath attached to it. Whether you are in private practice or a prosecutor, whether you’re a public defender or an in-house counsel, you are an officer of the Court. Each of you – each of us – has an obligation to leave our institutions of justice, and our country, better and stronger than we found them.

Love

Finally, what distinguished Edward Weinfeld from any machine was his capacity to love. Love for his country. Love for the law – which was deep and sincere. Love for his colleagues, whom he respected and cherished. Love for his law clerks, whom he regarded as his second family. And most of all love for his family – his wife Lillian, his children, and his grandchildren, including Amy, who is here today.

In this regard, if none other, I count myself Weinfeld’s equal. I share his love for this country and his love of the law. I too have colleagues whom I cherish. I also have law clerks who are my second family. Those clerks, many of whom are here today, inspire me. I am amazed at their talent and energy and commitment to public service, which they provide anonymously and at below-market rates. To say that I am a better judge because of their efforts is an understatement. But it’s more than that. They are a source of tremendous joy and pride, and I am grateful for the privilege of being part of their lives, not just in the year they clerk for me, but for the years and decades that follow.

And finally there’s my actual family – my wife Annie, and our three children, Marie, Monica, and Raymond. I’m grateful to them for allowing me to do what I’ve been doing for the past 20 years. I’m grateful to them for loving me unconditionally. I’m grateful to them for their humanity – for their own judgment, care, joy, patriotism, and love.

My wife Annie works as the athletic director of a high school, where she has made a deep impact on her students, far beyond the impact I can make as a judge. My daughter Monica is a first lieutenant in the US Army. My son Raymond is a midshipman in the Naval ROTC program at the University of Notre Dame. My daughter Marie is an environmental scientist who may end up saving the world itself. Each of them inspires me every day. I have no pretensions of being a great judge in the mold of Edward Weinfeld. But I am certain that the love of my family has helped me to be a better judge than I otherwise would have been.

***

Today, through the generosity of the New York County Lawyers Association, we celebrate the legacy and humanity of Judge Edward Weinfeld. I am honored to receive this award – named after a judge I revere and bestowed by an organization that I so admire – not because I deserve it, but because of what it represents. Even today, Judge Weinfeld reminds us of the nobility of our profession and the promise of our institutions of justice. He inspires us to be our best selves and to strive for excellence while embracing our humanity. While only a few in this room personally knew Judge Weinfeld, each of us can learn from his example. This event, in Judge Weinfeld’s memory, invites all of us to be more like him and to recognize the important role we play as judges, lawyers, and citizens of this great country.

In closing, let me just say thank you again to NYCLA for this tremendous honor; thank you to all of you for being here; and God bless the United States of America, today and always.