Judge Crotty’s Legacy of Pragmatism, Justice, and Cornell Clerks

by Ian McGullam

For almost two decades, a steady stream of Cornell Law students have launched their legal careers in the Manhattan chambers of Judge Paul Crotty, LL.B. ’67, of the U.S. District Court for the Southern District of New York. 

Crotty has made it a habit to always recruit a Cornell Law School graduate as one of his clerks. He’s managed it every year he’s been in office—save for 2009, but he made up for it a few years later by hiring Law School grads to fill both his openings.   

“On the basis of an interview that lasts at most an hour, you make a decision that’s going to bind you for a year,” Crotty said. “So, you’d better pick a good law school, and pick somebody who’s had a good record at law school, because those are the best guarantors of their ability to practice law.”

“I’ve been doing it for eighteen years now,” he quipped, “and I’m very lucky—I’ve not had a bad clerk yet.”

Judge Paul Crotty, LL.B. ’67

Carl Rizzi ’16 was one of Crotty’s many Cornell clerks, and now helps the tradition along as the Law School’s director of judicial clerkships. Crotty reaches out to Cornell every January, and Rizzi especially tries to flag the openings for students with the right combination of qualities to succeed in Crotty’s chambers—collegiality, work experience, a strong moral compass, not too much of an ideological bent. (A proclivity for the Big Apple doesn’t hurt, either.) “Some candidates underestimate their own chances due to grades, and I try to encourage them to be a bit more confident,” Rizzi said. “Especially with Judge Crotty, I think it’s important to apply because he’s looking for people he has chemistry with, and who bring some experience to the table.”

As a clerk, Crotty said, “you learn so much about what the law is and how to practice law, things that you never think of, and really are not taught.” It’s only fitting that, following his graduation from the Law School in 1967, his own clerkship with Judge Lloyd MacMahon, LL.B. ’38, in the New York Southern District Court was instrumental in setting him on his own, winding path to the bench. 

Crotty was instantly drawn to the diversity of work in the Southern District. “You had all kinds of great trials going on at the same time and great lawyers coming in,” he remembered. “The idea that you could pick up the newspaper and see the events of the day being recounted by the New York Times
and the Wall Street Journal—it was just a very exciting thing,
and I never forgot it.”

It would be some time before he returned in judge’s robes. Following his clerkship, Crotty spent the next two decades practicing at Donovan Leisure Newton & Irvine in New York City, punctuated by a stint during the 1980s working for the city as commissioner of the Offices of Financial Services, Commissioner of Finance, and Commissioner of Housing, Preservation, and Development. 

Crotty returned to public service in 1994 as New York City’s corporation counsel during the first term of Mayor Rudy Giuliani—who just happened to have been Crotty’s fellow clerk in MacMahon’s chambers. As the head of the city’s Law Department, he successfully argued before the U.S. Supreme Court in Agostini v. Felton, a notable First Amendment case in which the high court overturned its previous Aguilar v. Felton decision that had barred the city from sending public-school teachers into parochial schools to provide remedial education.

In 1997, Crotty shifted back to the private sector—this time the telecommunications industry, where he served as president of Verizon New York and Connecticut for close to a decade. “When my career slowed down just a little bit,” Crotty said, “the thought occurred to me that if I could get a judgeship, it’d be a perfect way to start a new career and keep me busy in doing some very meritorious public service work.” President George W. Bush nominated Crotty to the Southern District in 2004, and the following year he left Verizon for a new life as a federal judge after the Senate confirmed him, 95–0.

Ilana Pearl ’05 was hired as Crotty’s first clerk, and the two were sworn in on the same day. Watching Crotty learn to be a judge was an illuminating experience for Pearl, who went on to a career in corporate law and is currently a partner at  Cullen & Dykman. “It made him very humble,” Pearl said. He entrusted her and her fellow clerk with significant responsibilities, especially compared to her later clerkship with a senior judge where the imbalance between his deep experience and that of his clerks was evident in their relationship. “Judge Crotty knew what he was doing, but also recognized that the process of doing it from the bench was new to him,” Pearl said. “He was very deliberative about every decision, and very careful to get it right.”

“He entrusted you with a great deal of responsibility to work on those matters, and he also took the time to make sure you understood what was going on,” concurred Chris Connolly ’06, Crotty’s clerk in 2008–2009 and now an assistant U.S. attorney in the New York Southern District. “He valued your input and your advice and your thinking on the matter, which can be both a little daunting and also just an incredible thing as a young lawyer.”

When Phil Duggan ’21 clerked with Crotty in 2021–2022, he found an immediate connection with his new boss in their shared roots in Buffalo. In short order, a Buffalo Bills banner adorned the chambers.

When Phil Duggan ’21 clerked with Crotty in 2021–2022, he found an immediate connection with his new boss in their shared roots in Buffalo. In short order, a Buffalo Bills banner adorned the chambers.

“He brings a pragmatic approach to the bench,” perhaps informed by his blue-collar hometown, said Duggan, now an associate at Cravath, Swaine & Moore. “Other judges, in what is a fantastic court, are known to be very cerebral. That’s not to say Judge Crotty isn’t whip-smart. But I think he has more of a real-world perspective.” After being immersed in law school for so long, Duggan found Crotty’s approach refreshing. “You come out of three years of learning nothing but legal theory and abstract principles, only to see them applied real world by a real person who does care about the real-life consequences of how these decisions are going to affect litigants.”

The first case that landed on Duggan’s desk during his time in Crotty’s chambers involved the deadly 2017 collision between the guided-missile destroyer USS John S. McCain and a Liberian-flagged oil tanker, the Alnic MC. The judge went through the extra effort of procuring a “Silver Oar” to place in the courtroom, continuing a now rarely seen tradition observed by the Southern District Court of New York in admiralty cases dating back to the mace used by the court’s colonial-era predecessor, the Vice-Admiralty Court of the Province of New York. 

Everyone had to get up to speed on admiralty law, but Crotty had an extra edge: after getting his bachelor’s degree from the University of Notre Dame in 1962, he had served on a U.S. Navy destroyer. “There was more than one time where a sailor or a witness or a lawyer would start to explain a term to him about how the engine room works or what have you. And he stopped them gently and said, ‘Don’t worry, I’ve served on a vessel,’” Duggan remembered. “At one point, he even corrected one of the lawyers about where you fly the flag.”

As much as he’s known for his practicality and pragmatism, Crotty’s strong sense of justice also shines through. In one notable case in 2018, Crotty ordered the release of an undocumented immigrant who had been arrested by ICE while delivering pizza to a Brooklyn Army base and granted a stay on deportation proceedings. Rizzi, who was one of the judge’s clerks at the time, remembered Crotty musing during a hearing, “The powerful are doing what they want, and the poor are suffering what they must.” (Crotty’s eye for equity looks inwards, too—Rizzi recalled the judge advising his clerks to hire interns from local, lower-ranked law schools, reasoning that an internship with a federal judge would have a greater impact on their careers.)

Talk to a former Crotty clerk, and his dedication to making the clerkship experience a rewarding one is immediately apparent. Annie O’Toole ’16, a deputy federal public defender at the Federal Public Defender’s Office in the Central District of California, remembered how Crotty would volunteer to take on criminal duty in the role of a magistrate judge, so that his clerks could see him swearing out search warrants and dealing with emergency motions. “He went above and beyond to do those things,” she said. “He didn’t have to, but he did it because he thought it would be good for his clerks.” 

For O’Toole, watching deputy public defenders working in Crotty’s court solidified her desire to pursue that work. “I was really impressed by their devotion to their clients and how strongly they fought for each of them,” she said, and Crotty “believed in me and supported me, and that helped me see that I could do it too.”

Neil Kelly ’10, now an assistant federal defender in the New York Southern District, clerked for Crotty in 2012–2013 after having previously interned for the judge. One of the criminal cases before Crotty during Kelly’s clerkship involved two defendants, one of them represented by legendary criminal defense attorney Jerry Shargel, and the judge encouraged his clerks and interns to pay attention. “They were making the arguments so persuasive and interesting on both sides that he held it up as an example of how a case can be litigated at a high level,” Kelly said. 

And former clerks remain enmeshed in a vibrant network. The judge hosts regular clerk reunions, and his famous holiday parties offer more opportunities to mingle with each other, as well as with New York City notables. He married O’Toole and her husband; Rizzi’s third date with his wife was at one of those holiday parties. Former clerks described repeatedly reaching out to Crotty years after they had left his chambers at career transition points. “He was a mentor, even long after the clerkship,” said Pearl.

Now 83, Crotty has taken a reduced caseload along with Senior Judge status, but he’s enthusiastic about continuing the work as long as he can. “I’m happy that I have to still have the opportunity to serve the public in an important way,” he said. “I think the court is a richer place because of the experience that the senior judges bring.”

And, that body of experience is greater than any single judge. Ever the history devotee, Crotty said he has been struck by the through-lines in the legal system stretching back to the common law system’s foundation in the 1100s. “The essentials of a trial haven’t changed very much,” he said. “The experience I gained when I went to Cornell, when I went to clerk for a federal court judge, when I tried cases for Donovan Leisure, when I tried cases for the City of New York—you’re working with a construct that hasn’t changed much over time.”

Rizzi, who was one of the judge’s clerks at the time, remembered Crotty musing during a hearing, “The powerful are doing what they want, and the poor are suffering what they must.”

“How you try cases, the rules of evidence, the motions that you make, the strategies that you embark on are all pretty much the same. And there’s a direct linkage between the earliest days of jurisprudence in the current embodiment of those rules. As you go through this, you learn more about yourself, you learn more about the process. But the process was always there to educate you.”