New Pro-Defendant Decisions Signal Sea Change at New York’s Top Court

The rulings shed light on the leanings of Caitlin Halligan, the court’s newest judge and frequent tie-breaker.

Sam Mellins   ·   November 30, 2023
Court of Appeals judges stand and clap for Caitlin Halligan
Caitlin Halligan had never served as a judge when she joined the Court of Appeals — making her judicial leanings a mystery. | Don Pollard / Office of Governor Kathy Hochul

A recent spate of rulings suggests that New York’s top court is headed in a more progressive direction, especially concerning the rights of people accused of crimes. Caitlin Halligan, the court’s newest judge, has sided with the more liberal judges in several closely divided cases, often casting the deciding vote in favor of defendants’ rights.

Halligan’s votes shed light on her liberal leanings as a jurist — something that was unsure upon her ascension in April — and they could herald a dramatic change from the court’s prior makeup. Under the leadership of former Chief Judge Janet DiFiore, the Court of Appeals was a friendly place for prosecutors, and a hostile one for defendants. In her final year as chief, DiFiore and her allies on the bench ruled against defendants in the large majority of cases, including in rulings that expanded the power of police to question suspects or search private homes without warrants.

It’s hard to imagine the DiFiore court issuing last week’s opinion, written by Chief Judge Rowan Wilson and supported by Halligan, ruling that police had violated a defendant’s rights by entering his apartment to arrest him without a warrant. In a 2021 case, the DiFiore court explicitly approved similar entries in certain circumstances, over a dissent from Wilson. Last week’s ruling shows a shift from that stance, and it was just one of five recent rulings in which Halligan cast a key vote in favor of defendants.

“As we hoped, this court is showing a demarcation from past decisions,” said state Senator Brad Hoylman-Sigal, who chairs the judiciary committee. Hoylman-Sigal, along with other senators and advocates, touted the rulings as validation of their historic fight last winter, when the state Senate rejected chief judge nominee Hector LaSalle, the first time it had ever voted down a governor’s nominee to lead the Court of Appeals.

Even one of LaSalle’s most ardent backers praised Halligan’s votes for defendants’ rights.

“Judge Halligan has been a great asset,” said Senator Luis Sepúlveda, one of the few legislators to support LaSalle. “From my philosophy, we made the right choice with her.”

“It’s night and day from the horrible DiFiore court.”

—Senate Deputy Majority Leader Michael Gianaris

Last year, after DiFiore resigned amid a scandal, Governor Kathy Hochul nominated LaSalle, a judge on a state appeals court, to replace her. Progressive Democrats and labor unions were outraged. They said LaSalle’s judicial record was too conservative, citing rulings that they argued shielded “crisis pregnancy centers,” disadvantaged labor unions, and barred a criminal defendant from appealing his conviction. They rejected his nomination in February, and two months later, Wilson was elevated to chief judge from his existing seat on the court. Halligan filled Wilson’s spot as associate judge.

Though it’s still early, the recent pro-defendant rulings show the effect that political fight had, said Noah Rosenblum, a professor at the New York University School of Law who was a prominent opponent of LaSalle’s nomination.

“The evidence does not show that there is a durable liberal majority,” he said. “But as a result of not having LaSalle be the seventh vote on that court, New Yorkers have more rights.”

Caitlin Halligan is sworn in by Chief Judge Rowan Wilson on June 7, 2023.
Caitlin Halligan is sworn in by Chief Judge Rowan Wilson on June 7, 2023. | Don Pollard / Office of Governor Kathy Hochul

Before she joined the court, Halligan’s political leanings were unclear. She served as a clerk for liberal Supreme Court Justice Stephen Breyer, and she was nominated to a federal judgeship by President Barack Obama. But she had never actually served as a judge. As a lawyer, she had represented major corporate clients such as Chevron and UPS.

In addition to the case curtailing warrantless police searches, Halligan signed on to a decision by Wilson finding that a lawyer had violated his client’s right to effective legal assistance by pursuing a defense that was guaranteed to fail under existing law. In both cases, Halligan and the liberal judges overturned the convictions and sent the cases back to lower courts to be retried.

Those cases were redos from the court’s last term before Halligan joined. With a vacancy lasting for most of that term, the short-staffed court split three-to-three and ordered do-overs in multiple cases — guaranteeing Halligan the deciding vote.

She broke the tie in another criminal case last week, this time writing an opinion ordering a new trial for a defendant who had been convicted of illegal gun possession. By allowing prosecutors to use prior gun-related incidents, including a decade-earlier conviction for a similar crime, as evidence, the lower court had prejudiced the jury against the defendant, Halligan argued. New York law generally prohibits prosecutors from using previous unconnected crimes as evidence against defendants.

“It’s night and day from the horrible DiFiore court,” said state Senate Deputy Majority Leader Michael Gianaris. “I have great confidence in the chief judge and a number of the judges who are taking this approach.”

In another 4–3 ruling, Halligan joined an opinion stating that requiring a defendant to register as a sex offender for a non-sexual crime — unlawful imprisonment of a minor — violated his constitutional rights. Though his crime didn’t involve any sexual contact, state law defined it as a sex crime. In an opinion by Judge Jenny Rivera, the court removed the sex offender designation.

Rivera argued in favor of overturning a 2009 Court of Appeals case that had allowed sex offender designations in similar situations. While Wilson supported Rivera’s opinion, Halligan and Judge Shirley Troutman, who is also more moderate, didn’t join that part of it, meaning that the 2009 case stands for now.

The District Attorneys Association of the State of New York declined to comment for this story.

These rulings don’t mean that the court has a solid liberal bloc — as it once had a solid conservative one.

In one November case, Troutman joined the more conservative judges to uphold a defendant’s convictions for marijuana and gun possession. Halligan, joined by Rivera and Wilson, wrote the dissenting opinion, arguing that police had unjustifiably stopped the defendant’s car. In another, Halligan and Troutman both joined the conservative judges in ruling that handcuffing a suspect doesn’t automatically mean that police have to read them their rights.

In another key ruling last week, which took away the disciplinary powers of Rochester’s police accountability board, the conservative judges claimed victory with the support of someone who isn’t even a member of the top court: Judge John Egan, Jr., who sits on one of the state’s four mid-level appeals courts.

Troutman had recused herself from the case, which might have triggered a deadlock under a different chief judge. But Wilson has signaled that he intends to make more frequent use of a provision in the state constitution that allows lower appeals court judges to sub in when judges from the top court recuse themselves.

This practice has been permitted by the state constitution for decades, but Wilson’s predecessors used it relatively infrequently.

Former Chief Judge DiFiore was known for picking substitutes who shared her political leanings, ensuring rulings that she was favorable to. She twice selected LaSalle, her almost-successor, who agreed with her both times.

Wilson has opted for a system marked by unpredictability: cycling through all of the four appeals courts’ judges, in order of seniority.

This means that relatively unknown judges cast key votes. Egan, for example, cast the deciding vote not only in the case ruling in favor of Rochester’s police department, but also in another case increasing the legal protections that bicycle riders have against being stopped by police.

That result shows that even if Halligan doesn’t participate in a case, there’s been a sea change, said Steven Zeidman, professor at City University of New York School of Law.

“There seems to be much clearer recognition of individual rights and liberties,” Zeidman said. “The pro-prosecution bent is no longer in place.”

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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