If Rowan Wilson could pick two words to best describe his judicial philosophy, he would choose “progressive pragmatist.”
Wilson, who serves as the chief judge of the State of New York, said that description came from a class of Albany Law School students he visited as a guest speaker. As Wilson tells it, one student in the class, which focused on the Court of Appeals, asked him to lay out his judicial philosophy. Instead of answering the question himself, Wilson threw it back to the room of prospective attorneys to figure it out.
“The thing they arrived at was as a ‘progressive pragmatist,’” Wilson said in an interview with amNewYork Law. “And I said, ‘I’ll take that.’ I think I am pragmatic. I think I am looking for solutions that work in the real world.”
A prime example of that pragmatism, Wilson said, is how he goes about writing his opinions. He said that he tries to write at a 12th-grade level, while using real-world analogies to make his decisions more accessible and relatable to the public.
“Ninety-eight percent of what I write, I really think that a 12th grader could pick it up and understand it,” the chief judge said. “There’s probably 50% that an eighth grader could pick up and understand.”
The idea, Wilson said, is that “the law really belongs to the people. You’re trying to give people guidance, and if the guidance is obtuse, it doesn’t really serve that purpose. And you’d like to have it so that people can read it and understand it.”
Wilson has put the ethos of progressive pragmatism at the center of his approach to the job of chief judge since stepping into the post in April 2023. As chief judge, Wilson has dual roles of sitting atop the seven-member state Court of Appeals — New York’s highest court — and heading the sprawling statewide judicial system. In effect, Wilson is tasked with overseeing about 3,600 state and town and village judges, plus 15,500 non-judicial employees, working in 300 state courts and 1,300 town and village courts across New York’s 62 counties — according to the Office of Court Administration.
Wilson sailed through the confirmation process for the position, buoyed by a strong 40-member majority in the Democrat-controlled state Senate, after being nominated by Gov. Kathy Hochul.
However, Wilson was Hochul’s second nominee. She put his name forward after her first pick, Judge Hector LaSalle, was rejected by state lawmakers in early 2023. The overwhelmingly Democratic state Senate rejected LaSalle because he was seen as too conservative.
Before his elevation to chief judge, Wilson spent five years as one of the court’s six associate judges. He served under former Chief Judge Janet DiFiore, who was appointed by ex-Gov. Andrew Cuomo. DiFiore was widely considered to have taken the court in a more conservative direction.
Wilson is known for steering the court in a far more liberal direction — something the state lawmakers who pushed for his nomination had hoped for.
Wilson’s path to leading the Empire State’s top court was hardly straightforward.
Wilson was born in Pomona, Calif., and grew up in Berkeley during the 1960s and 1970s, at the height of the civil rights movement and the Vietnam War. He described Berkeley as a place where progressive activism was inescapable.
“When I was a kid in Berkeley, almost every stop sign had the word ‘Nixon’ spray-painted onto it,” Wilson said, as many people had contempt for the late Republican president.
Wilson then ventured to the East Coast to attend Harvard University for college and, subsequently, Harvard Law School. He was admitted to the California bar in 1985 and clerked for Judge James Browning, then chief judge of the Ninth Circuit.
With the goal of becoming a law professor, Wilson moved to New York City in the late 80s and worked for the white shoe law firm Cravath, Swaine & Moore, hoping to gain experience that would make him more marketable to law schools.
Wilson said he found the corporate work intellectually challenging, and it allowed him to devote a significant chunk of his time to pro bono work.
After 25 years at the firm, Wilson applied for a spot on the Court of Appeals. Cuomo appointed him in 2017.
Choosing the best path forward
Since taking the reins as chief judge last year, Wilson has emphasized the benefits of problem-solving courts.
He is expanding those courts — known as “problem-solving courts” — that attempt to address the underlying issues that bring people into the criminal justice system. These specialized courts address specific problems; for instance, there are drug and mental health treatment courts, community courts, veterans’ courts, and alternatives to incarceration courts.
Wilson said he has made efforts to bolster and expand problem-solving courts by securing more funding, shifting judges to those courts, and bringing in more resources.
He is also working with state lawmakers to pass the “Treatment Not Jails Act” — a bill introduced by state Sen. Jessica Ramos (D-Queens). The legislation would require all of the state’s 62 counties to have mental health treatment courts and mandate that judges undergo additional training.
Wilson said that his office identifies bills that could impact the courts as soon as they are introduced. The court adopts a position and works with lawmakers on the bill’s language to address concerns before it gets out of committee.
“The law really belongs to the people. You’re trying to give people guidance, and if the guidance is obtuse, it doesn’t really serve that purpose.”
The chief judge made the unusual move of ceding much of his first “State of the Judiciary” address earlier this year to individuals who said their lives were greatly improved by problem-solving courts.
“I did something really odd, I brought a bunch of people who’ve been through these specialty courts as litigants to talk about what their experiences were and how these things had sort of changed and improved their lives,” he said.
He pointed to one woman who spoke, Keisha Nankoosingh, who was a heroin addict and had gone through a diversion court. It worked for her, but it did not work for her husband, who went through the same process but ultimately died.
“She recounted this whole story, she was in tears, the audience was in tears,” Wilson said. “But she’s fine, and she’s got her kids, and they’re doing well. You could have arrested and thrown both [her and her husband] in jail, taking the kids, put the kids in foster care somewhere, which is another nightmare, but that didn’t happen.”
Another of Wilson’s efforts is to improve the court’s messaging. He said that he is trying to communicate to judges the idea that courts should not just be viewed as arbiters of right and wrong, but instead as an institution that can address critical issues, similar to other branches of government.
Whether it’s a criminal or family matter, Wilson said, the facts have happened. “You can’t undo those facts. …So the question is: we are where we are. What is the best path forward? And that is different from asking the question: who was right and who was wrong in getting to where we got? We got in here. What’s the best way to move forward?” he said.
More cases equal more guidance
Another area where Wilson has tried to reform the Court of Appeals is by increasing the number of cases it hears. During DiFiore’s tenure the average number of cases heard per year dropped from that of previous administrations.
Wilson said there are two main reasons why he thinks it is important for the Court of Appeals to take on cases. One, the more appeals the court hears, the greater the amount of law it has rendered an opinion on. “If our job is to set the law of the state of New York, and we hear 50 cases a year, we’re not really touching very much of the law,” Wilson said. “And if we hear 120, 130, 150, there are many more areas of law where we can provide some guidance.”
The second reason, Wilson said, is that the only way to teach lawyers to argue in front of the Court of Appeals is to give them a chance to do so. Wilson said one lawyer who appeared before the court recently had been practicing for 42 years and said he had never had the opportunity to argue before the Court of Appeals.
“When the docket falls and falls and falls, there are fewer chances for people to argue in the Court of Appeals,” Wilson said. “In some ways, it’s an important public service, I think, to provide the opportunity for people to have their cases heard.”
Wilson said that unanimity on the Court of Appeals can be a good thing, but he does not believe in forcing his fellow judges to agree.
He said he encourages discussion among the justices, and they have become more amenable to modifying their positions in response to their colleagues’ arguments. Those dynamics, he said, have led to fewer dissents and more unanimous opinions over the past year and a half.
“I think what I’ve seen in the last year or so is a lot more flexibility by everybody on the court,” Wilson said. “You’ll see, I think, a greater number of unanimous opinions over the last year and a half than you saw before.”
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