Chief Judge Rowan Wilson is never bored

New York state Chief Judge Rowan Wilson gets bored easily.

That’s not a dig at the jurist – those are his own words. Wilson enjoys being a generalist, flitting between topics that can hold his attention for just long enough to learn about them, without ever becoming a subject matter expert on any particular area of law.

It makes his dual role as the top jurist on the state Court of Appeals and head of the state’s sprawling judiciary branch a perfect fit. “I’m often tired – I’m never bored,” Wilson told City & State in an interview at his Manhattan office. Each case offers Wilson an opportunity to learn something new about a topic he may have never considered. “The fun for me is learning,” he said. “It’s the challenge of not knowing and trying to find your way to a solution.” As for the administrative side, you try running a complicated organization of 16,000 employees across the entire state and see whether you get bored.

He may never be bored, but Wilson is often quiet. In a field with big personalities and even bigger egos, Wilson’s humble, unassuming nature is an anomaly. When the interview for this story ran quite long, making him late for a lunch appointment, Wilson brushed off an apology. “I don’t wear a watch,” he explained. “Then I don’t have to worry about time.” Associates who have known him for years said they have rarely, if ever, seen Wilson angry.

His demeanor, matched with a sharp but subtle sense of humor, has served him well in both the courtroom during cross examinations and in his interpersonal relationships. “So much in life is hard,” said Rick Jones, a founding member of Neighborhood Defender Services, a nonprofit legal assistance organization whose Harlem board Wilson served on for over two decades. “Working with Rowan and being friends with Rowan … is easy.”

For a little over two years, Wilson has led the state’s judiciary system. Chief judges have long sought to leave their mark on the oft-overlooked third branch of state government, and Wilson is no different. Having emerged from an unusually political appointment process and succeeded a particularly polarizing chief judge, his attempts to restore the court’s reputation and his focus on the human impact of the court’s work have put him well on his way to leaving a legacy that goes beyond his distinction as New York’s first Black chief judge.

Wilson came to New York by way of California. The oldest of three children, he learned responsibility early on in order to help his blind mother. “I essentially functioned as her eyes, which worked its way up to when she was getting a Ph.D. at UC Berkeley,” Wilson said. “I was taking her to her seminars in the afternoon after school, and reading some of her coursework to her.” That sparked an early interest in education.

Wilson attended Harvard for both undergrad and law school. After graduation, he spent two years clerking for the late Judge James Browning, then the chief judge of the U.S. Court of Appeals for the 9th Circuit, before moving to New York City to take a job at Cravath, Swaine & Moore. He would spend the next 30 years in the white-shoe law firm’s litigation department, trying a large number of cases on a plethora of topics – perfect for keeping his attention.

From the start, Wilson made an impression at Cravath. “Rowan is an off-the-charts brilliant guy,” said Robert Baron, who started at Cravath a few years before Wilson and now serves as the firm’s general counsel. “I think a lot of people are described as extraordinary intellects who are merely very bright. Rowan isn’t very bright – he is an exceptional intellect, and that was clear really early on.”

Wilson’s litigation work often brought him around the country for different trials, requiring him to set up for weeks or months at a time with one or two other lawyers from the firm. “You’re spending a lot of time together, and if you don’t like each other, that becomes a pretty unpleasant experience,” said Evan Chesler, Cravath’s former chair. Things were never unpleasant with Wilson. “At a personal level, he’s just a joy to be with and work with,” Chesler said. “He’s funny, has a great sense of humor and he has a sort of wry view of the world.”

Several years into his career at Cravath, Wilson was offered the opportunity to take a teaching position at UC Berkeley. Wilson had always planned to eventually go into education, and this was a dream position – but he felt obligated to stay at Cravath for a little longer. He was close to making partner at the firm, which would make him the first Black partner in Cravath’s history. He said as much to the woman offering the teaching job. “I said, ‘But regardless of what the (partner) decision is, after that decision, I’d love to come back and talk to you,’” he recalled. “And she laughed at me, and she said, ‘We’re never going to hear from you again.’ She was right.”

Wilson made partner in 1991 and ultimately decided to stick with the job for many more years. More than three decades later, Wilson once again broke a historic barrier – becoming the state’s first Black chief judge.

Judge Wilson isn’t the only Wilson in his Manhattan office. On his desk sits a volleyball with a crude, red face painted on it – which film lovers might recognize as Tom Hanks’ sole companion and main acting partner in the movie “Castaway.” Wilson (the human judge) is a fan of movies, particularly animation and rom-coms (his favorite is “Tootsie”), but the story behind the item has little to do with his personal affinity for cinema.

Several years ago, Wilson delivered the keynote speech at the Albany County Bar Association’s annual Court of Appeals Dinner. As part of his speech, he prepared gag gifts for each judge on the court, including himself. And so came the “Castaway” reference. “I was dissenting a lot back then, and the setup for that was if you find yourself alone on an island of dissent, you might want to buy one of these,” he said with a chuckle.

His journey to that island began in December 2012. Wilson was home in New York, fresh off a big trial in Alabama and with another trial coming up at the start of January. In between preparing for the case and finding time for holiday shopping, Wilson was being hounded by a friend about applying for a vacancy on the Court of Appeals. When Wilson finally decided to apply for the position, he didn’t think it would go anywhere. But he wound up on the Commission on Judicial Nomination’s short list of recommendations for then-Gov. Andrew Cuomo.

Cuomo didn’t pick him that year, but Wilson continued applying and kept making the short list. In 2017, Cuomo decided to nominate Wilson. “Probably the best thing Cuomo did in his tenure, and certainly a legacy that he should look back on proudly,” said Jones of Neighborhood Defender Services.

Under the leadership of then-Chief Judge Janet DiFiore, the Court of Appeals leaned more conservative, and Wilson often found himself dissenting during his years as an associate judge, generally alongside Judge Jenny Rivera. Even when he disagreed with the majority, though, his legal analysis garnered him praise. “He’s a solid judge in the sense of knowing the law, and I can say he’s dissented in three cases of mine, which he clearly was right,” said Michael Hutter, a professor at Albany Law School and a Republican appointee to the Commission on Judicial Nomination. “His analysis was so terrific, he saw things that I overlooked. That’s how good he is.”

Wilson’s pointed writing style quickly gained attention. Vincent Bonventre, a professor at Albany Law School, recalled a particular criminal case in which Wilson wrote the dissent. “The way he talks about it is like you and me, if we met on a street corner, ‘You hear about that son of a bitch? All he did was steal a can of Red Bull,’” Bonventre said. “That’s the way Wilson writes, like you can’t miss the reality of what happened.” He added that in his experience, many judges don’t know how to write particularly well, let alone as poignantly as Wilson.

DiFiore stepped down in 2022, leaving a leadership vacancy on the court at a time when Democrats and criminal justice reformers were hoping to shift the court to the left. In particular, activists wanted to see more judges on the court who came from diverse professional backgrounds – not just the former prosecutors, like DiFiore, who often wound up on the bench.

The Commission on Judicial Nomination put out a short list at the end of 2022 – one that didn’t include Wilson, nor fellow left-leaning judges on the Court of Appeals Rivera and Shirley Troutman. “I was surprised, I don’t think it was a good decision,” Wilson said. The list did include Justice Hector LaSalle of the Appellate Division’s Second Judicial Department, whom Gov. Kathy Hochul decided to nominate to the chagrin of criminal justice advocates and labor leaders.

A growing number of Democrats in the state Senate opposed LaSalle’s nomination, but Hochul refused to pull his name. So in an unprecedented vote, the state Senate rejected LaSalle’s nomination, which led Republicans to accuse Democrats of cravenly politicizing the judiciary. A new short list of candidates was drawn up that included Wilson, who was favored by progressives. Hochul nominated him for the chief judge position, and lawmakers quickly confirmed him.

The contentious saga led to concerns, particularly from the GOP, that Wilson would effectively be beholden to Democrats. “He’s not providing the check on the Legislature that I think is appropriate for the judiciary,” said state Sen. Anthony Palumbo, the ranking member on the Judiciary Committee and a strong supporter of LaSalle. “He’s a very qualified man, a very qualified jurist, but I feel as if politics has been – it’s had too much of a role in the court.”

Wilson has been criticized for selecting relatively liberal judges to serve temporarily on the court in cases where some members of the Court of Appeals have recused themselves. “It was clear he was making those selections based upon how he thought they would vote, and they would vote with him,” said Hutter, who believes LaSalle would have made a better chief judge than Wilson. Hutter also pointed to the redistricting case under Wilson, which permitted Democrats to ultimately get another chance to draw congressional lines. Newly confirmed Judge Caitlin Halligan – considered the tiebreaking vote in the redistricting case – recused herself, and Wilson vouched in Judge Dianne Renwick, the presiding justice of the First Appellate Division. She voted to redraw the congressional map. Palumbo brought up the contentious Harvey Weinstein decision, in which Wilson vouched in two judges who voted to throw out his conviction.

Others felt Wilson has managed to move past the politics that preceded his confirmation. “That crisis made Judge Wilson’s task even greater, because that affected the morale of the judiciary,” said Assembly Member Charles Lavine, the chair of the Judiciary Committee. “To his great credit and to the great credit of (Chief Administrative Judge Joseph) Zayas, Judge Wilson was able to overcome that and reestablish trust top-down in the judiciary.” State Sen. Brad Hoylman-Sigal – who played a key role in rejecting LaSalle’s nomination as the chair of his chamber’s Judiciary Committee – noted Wilson has taken positions on cases that Democrats haven’t agreed with. “He’s a public intellectual and also a very nice person, and those are two qualities that are pretty rare in public and in politics,” Hoylman-Sigal said.

Wilson took over the judiciary system at a somewhat turbulent time for the state’s highest court. Under DiFiore’s stewardship, the Court of Appeals itself was widely seen as fractured, with tensions between the judges occasionally spilling into public. The court’s caseload had decreased drastically, and the general perception of the court system had declined. “Janet DiFiore, she was a disaster,” Hutter said. “She didn’t know what the hell she was doing, quite frankly.”

Bonventre also described her years as dysfunctional. “I don’t necessarily think the problem was her, although she certainly wasn’t able to remedy whatever the problems were,” he said. “But there were some real dynamic problems in that court, you could tell people were not happy.” Before stepping down as chief judge, DiFiore faced scrutiny over potentially unethical behavior, including questions regarding a judgeship for her daughter and a conflict with the head of the court officers union. DiFiore could not be reached for comment.

Generally, observers said both the Court of Appeals and the court system as a whole has improved under Wilson since that time period. “He has restored his court to its rightful position as the premier state high court in the land,” said Tom Moore, a top litigator with KDLM. Moore often interacts with lawyers across the country, and he said Wilson’s reputation precedes him. “The word is out, believe me,” he said. “Whether they’re in Los Angeles or Dallas or Minneapolis, they know who the chief judge of New York state is, Rowan Wilson, and he’s universally loved and admired, admired by everybody.”

Wilson has received praise for increasing the Court of Appeals’ docket, with a particular focus on trying to take more criminal cases. The workload sharply decreased under DiFiore, with the number of yearly cases heard dropping from over 200 to an average of 80 or 90. Wilson got that number back up to around 120 per year. He said the court is working quickly to decide cases, while applications for appeals have remained down since the COVID-19 pandemic. “I think we’re handling the cases as well, we’re discussing them in meaningful ways,” Wilson said. “We’re writing pretty good opinions, and the Court of Appeals side, I think, is really in pretty good shape.”

Wilson’s amicable demeanor and easy conversation style has also seemingly improved the collegiality among judges on the Court of Appeals. “We do spend a good amount of time in conference, each of us respectfully talking about our views of the case,” said Rivera, who declined to directly compare Wilson to his predecessor. “And I think in that way, it’s much more intellectual dialogue at the court, which was the case when I first came to the court.” Former Chief Judge Jonathan Lippman, the first chief judge Rivera served under, also praised Wilson. “This court, the Wilson court, is not a fractured court,” he said. “It’s a court that, in many ways, reflects the persona of the chief. … He knows how to deal with disagreement without being disagreeable.”

If there’s one word to describe Wilson’s approach to his role as the head of the court, it’s “unorthodox.” Wilson used the term himself 11 times during his first State of the Judiciary address in 2024, which was indeed quite unorthodox. Its central tenet came at the end of Wilson’s introductory remarks: “The focus of the judiciary must be on the people we serve.”

Wilson ceded most of his time to ordinary people who had benefited from alternatives to incarceration like treatment court, community court and other diversion programs meant to help people stay out of prison and traditional courtrooms. Wilson’s address earlier this year was even more unorthodox. To highlight his legislative agenda, which included sentencing and parole reform, he featured both formerly and currently incarcerated people to speak about their experiences. “Rowan Wilson is someone who understands humanity and understands human beings and their importance, and that’s what the court system is all about,” Lippman said.

Wilson has made it an ongoing mission to improve the image and reputation of the state court system, especially given the public’s negative perceptions of the federal courts. “It’s important that people know what we are,” he said. “They see we’re human beings, that we’re trying to do a good job, that we – to the extent we can convey this – care about them.” He has completely overhauled the judiciary’s communications department and even set up a booth at the New York State Fair for the first time. “It’s one small way of many things we’re doing to try and increase the visibility and the good things that are happening in the court system,” Wilson said.

As the first person of color to serve as chief judge, Wilson knows he has become an important symbol, even beyond his unorthodox stewardship of the state judiciary. “I always, even to this day, kind of underappreciate how much things like that mean to other people,” he said. “So many people have told me that these sorts of things matter, and I think it’s starting to sink in a little bit.”

It has certainly sunk in for others in the profession. Nicole Lester Arrindell, president of the Metropolitan Black Bar Association, called Wilson’s appointment inspiring. “I think it also is a good signal, particularly when I think of our members, to every lawyer, but also law students, young lawyers, that they belong in this profession and that they can seek even the highest levels of service in this profession,” she said, adding Wilson offers a “powerful combination” of “excellence with intentional inclusion.”

At 65 years old, Wilson is only five years away from the mandatory retirement age on the Court of Appeals. He wants to make the best and most effective use of his time leading the state judiciary to leave a lasting legacy. “I don’t want to waste my time on something that has no prospect of achievement,” he said of previous chief judges’ dreams of massively restructuring the state court system. “I’m trying to work with what we’ve got to make that better, instead of trying to create something that we don’t have.” And there’s more than enough in-the-weeds, nitty-gritty issues of importance most of us rarely think about to keep Wilson occupied for years.

Wilson still has a vivid memory from his time clerking with Browning as a young man. The pair were the last ones in chambers one evening, and Browning took a different path out than usual, walking through Wilson’s office. “I think knowing that I was going to be there a lot later than he was … he says to me, ‘You know, this is the best job you’re ever going to have,’” Wilson recalled. But Browning had a second thought. “He opened the door from the hallway, stuck his head back in and said, ‘Unless you have my job someday.’”

The chief judge of the state Court of Appeals isn’t quite the same as a chief judge for a federal appeals court circuit, but for Browning’s meaning, it’s pretty darn close. And so far, as he spends each day never bored, Wilson can’t say his old boss was wrong.