New York’s Top Court Just Wrapped Up a Chaotic Term. Here’s What We Learned.

Former Chief Judge Janet DiFiore’s resignation broke a conservative lock on the Court of Appeals.

Sam Mellins   ·   June 22, 2023
Dramatic photo of the Court of Appeals in Albany, New York
Court watchers now have a clearer window into the body’s decisions as a whole. | Matt Wade

New York’s top court finished its term last week, closing out a tumultuous year that saw the court gain a new, left-leaning chief after the state Senate shot down the governor’s first choice for the role. The leadership change raised the possibility that a court previously dominated by a conservative bloc of judges would see a new liberal era. Instead, the court has become a battleground.

The court’s ideological blocs have begun to erode in the year since former Chief Judge Janet DiFiore’s sudden resignation. The court still has recognizable ideological fissures — but only to an extent.

In its next term, which begins in September, the court will weigh cases on issues ranging from the rights of New Yorkers suspected of crimes to the legality of New York City’s property tax system — and its rulings won’t be as easy to predict as in the past.

Chief Judge Rowan Wilson and Judge Jenny Rivera are consistently the most liberal judges on the court, while Judges Michael Garcia, the court’s only Republican, and Madeline Singas are its most conservative. But in the term that just ended, Judges Anthony Cannataro, Shirley Troutman, and Caitlin Halligan didn’t closely ally themselves with either side.

One measure of the shift: In the court’s final year under DiFiore, defendants lost three quarters of the criminal cases the court heard. This year, there was a nearly even split between wins for defendants and for prosecutors.

Last year, DiFiore, Garcia, Singas, and Cannataro voted as a bloc in nearly every case. In July, shortly after the term ended, DiFiore’s unexpected resignation amid an ethics investigation kicked off a fierce battle to replace her and initiated a temporary period of judicial gridlock. In February, the state Senate rejected Governor Kathy Hochul’s nomination of Hector LaSalle for chief judge, an unprecedented move prompted by concerns that his judicial record was too conservative. In April, the body confirmed Wilson, already one of the court’s most liberal judges, to the chief spot by a wide margin. Halligan, a private attorney and former US Supreme Court clerk, was confirmed as an associate judge the next day.

Judge Anthony Cannataro, who joined the court in 2021, never voted against DiFiore during the year they served together, joining the conservative bloc in numerous rulings in favor of corporate power, landlords, and, particularly, law enforcement. With her gone, he’s broken ranks several times to join the more liberal judges, though he still votes with the conservatives more often.

“When you had Janet DiFiore on the court, you knew you had to convince her” and the judges who voted in lockstep with her, said Robert Rosborough, an attorney at Albany-area law firm Whiteman Osterman & Hanna LLP who argues cases before the Court of Appeals. With DiFiore gone, “You’re not necessarily saying, ‘I have to argue this one particular way because I know on one side there are four votes.’”

Halligan has heard only a few cases since joining in April, and it’s not yet clear where she’ll fit in. Shirley Troutman, who was Hochul’s first appointee to the court in 2022, continued to be a swing vote, usually but not always joining the conservative side in split cases.

“You’re not necessarily saying, ‘I have to argue this one particular way because I know on one side there are four votes.’”

—Robert Rosborough, Whiteman Osterman & Hanna LLP

In March, Cannataro and Troutman joined Wilson and Rivera to overturn a 2015 rape conviction because prosecutors in the case had waited four years to bring charges. The 4–2 majority ruled that the delay, and the fact that the prosecution couldn’t explain why it took so long, violated the defendant’s right to a speedy trial under the New York State constitution.

Allowing the conviction to stand would mean that prosecutors could “delay investigation of a serious crime for years without any explanation or excuse,” Wilson wrote, concluding that the state constitution’s guarantee of prompt prosecution “benefits defendants, victims and society at large.”

Prosecutors denounced the ruling, which came shortly before Wilson’s confirmation as chief judge, and the New York City chapter of the National Organization of Women called for the state Senate to reject his nomination because of it.

But defense lawyers cheered the decision. “It’s about upholding the constitutional principle of right to a speedy trial,” said Yung-Mi Lee, president of the New York State Association of Criminal Defense Lawyers. “Every prosecutor in this state is aware that the consequence for violating the right to a speedy trial is a dismissal.”

Throughout the year, Wilson and Rivera were on the winning side of more decisions than they had been previously. During DiFiore’s last year, they wrote a combined total of six majority opinions and 22 dissents. This past year, they wrote 17 opinions and 19 dissents. (DiFiore, by contrast, was in the majority in every single case of her last year.)

In several cases, Cannataro and Troutman joined Garcia and Singas in opinions issued over Rivera and Wilson’s dissents, including three cases ruling against New Yorkers attempting to sue local governments for negligence.

In one case, Staten Islander Dora Howell sued New York City after police failed to enforce multiple orders of protection that she had obtained against Andre Gaskin, her severely physically abusive ex-partner. Despite Howell’s repeated pleas for the police to take action, Gaskin kept attacking her, and in November 2008, he pushed her out of a third floor window, shattering her spine. In 2009, Gaskin was arrested for the assault and violating the orders of protection, pleaded guilty to assault and criminal contempt, and spent almost five years in prison.

This year, the Court of Appeals shot down Howell’s efforts to receive compensation from the city for failing to protect her. The court ruled 4–2 that despite the orders, the police “did not voluntarily assume a special duty” to guard Howell from her abuser. The majority opinion, which was not attributed to any of the judges, said that Howell “could not have justifiably relied on any promises made” by the police to enforce the orders of protection. (The Court of Appeals created the concept of a “special duty” requirement in the mid-twentieth century to limit when New Yorkers could sue local governments.)

In April, Howell, 43, was found dead from a gunshot wound beneath the floor of a Staten Island basement. No suspects have been named in connection with the killing.

Wilson wrote a scathing dissent. “Orders of protection are supposed to mean something,” he wrote, calling the police’s inaction a “dereliction of their duties.”

The court relied on similar logic to toss other lawsuits against local governments. In one, Erie County caseworkers had failed to intervene in the physical and sexual abuse and eventual killing of an intellectually disabled woman despite numerous complaints and visits to the home where the abuse took place. In the other, the court ruled that a Long Island town was exempt from liability for a crash that occurred when one of the town’s firefighters ran a red light and crashed into a passenger car.

Court of Appeals expert and Albany Law School professor Vincent Bonventre said that the decisions “mean that it’s very, very difficult for a citizen to show that any kind of duty was owed to them.”

“When you have the police department, or the fire department, or other municipal officers, directly involved with an individual and directly reassuring the individual — I don’t know how you get a special duty beyond that,” he said.

In two other cases, the same four-judge majority issued rulings narrowing the rights of criminal defendants to present evidence in their own defense — in one case, text messages recovered using new technology that didn’t exist at the time the defendant was convicted, and in the other, information about the violent history of the man the defendant was charged with attacking. Wilson and Rivera dissented in both cases.

Most of this year’s cases were decided without Halligan, who has only ruled on a few cases since joining and doesn’t appear to have broken any ties so far. But next year, her vote will likely prove critical in cases that concern key issues for the rights of New Yorkers.

Before Halligan was confirmed, the short-staffed court ordered that seven cases be reargued at a future date, likely because the judges deadlocked three to three. The cases concern such issues as potential evidence tampering by police, protections against police searches for bike riders, and requirements for warrants before home searches.

If the other six judges maintain their previous stances, Halligan will cast the deciding vote when the court rehears these in the fall — which should reveal more about her political leanings.

Compared to recent history, court watchers now have a clearer window into the body’s decisions as a whole. Under DiFiore, the court delivered many of its rulings in the form of so-called “memorandum opinions” — brief, unsigned rulings that offer a bare outline of its reasoning. In DiFiore’s last year, more than half of the court’s decisions came in this form.

Court watchers have critiqued the use of memorandum opinions for being less carefully reasoned than full opinions and for failing to provide guidance to lower courts. This past term, only a third of the court’s decisions were issued in the form of memoranda.

“The more the court gets away from the memorandum and toward providing the public a full analysis of each legal issue they’re deciding, the better,” Rosborough said. “You should understand who’s doing the writing and why they’re reasoning the way they are.”

The court is also likely to hear more cases each year going forward. Both Halligan and Wilson said at their confirmation hearings that they think the court should expand its docket, which DiFiore deliberately shrunk during her tenure to a fraction of its former size.

“It’s too early to tell where it’s going to go,” said Steve Zeidman, a professor of criminal defense at the City University of New York Law School. “That four-person bloc just seemed written in stone.”

Eleanor Gonzales contributed research.

Sam Mellins is senior reporter at New York Focus, which he has been a part of since launch day. His reporting has also appeared in The San Francisco Chronicle, The Intercept, THE CITY, and The Nation. 
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