The questions from the judge came fast and often, frequently interrupting the personal lawyers of President Trump and the district attorney — and picking apart their arguments.
On an especially cold February day earlier this year on the 23rd floor of Manhattan's Daniel Patrick Moynihan United States Courthouse, Judge Alvin Hellerstein was hearing arguments to (again) decide whether the president could nix his hush money payment conviction.
Trump was convicted in New York in 2024 for falsifying business records to hide payments made to adult film actor Stormy Daniels, to keep her quiet about a sexual encounter between the two, which occurred years before he was president.
Hellerstein previously weighed in on this case — twice denying Trump's request to move the case to federal court.
But the 2nd U.S. Circuit Court of Appeals sent the case back to Hellerstein in November, ordering him to further review whether the Supreme Court ruling on presidential immunity applied.
After two days of observing Hellerstein in court, for this article, it became clear this level of questioning is customary for the long-sitting federal judge.
At 92 years old, Hellerstein is older than the average age of a federal judge by more than 20 years. (The average age of federal judges was about 68 as of 2024, according to data from the Federal Judicial Center.)
He serves as senior judge on one of the most prestigious and influential courts in the nation: the U.S. District Court for the Southern District of New York.
But he does not strike an intimidating figure.
His small stature and careful, halting steps between chambers and the bench hint at his age. But those who have worked with him or presented cases in his court say that outward appearance masks a sharp, deeply engaged jurist with an unwavering commitment to the rule of law.
The Maduro case presents thorny legal questions
Questions over Hellerstein's capacity and age have come up as he takes on one of the most complex legal cases of the Trump administration: the federal prosecution of former Venezuelan leader Nicolás Maduro and his wife, Cilia Flores.
On Thursday, Maduro's case heads back to court for a pretrial hearing to address his lawyer Barry Pollack's request that the court intervene after the Trump administration blocked the Venezuelan government from bankrolling his defense, according to court documents.
It's just the beginning of a host of thorny legal issues that are likely to arise from this case, experts say.
A core issue centers on how the former head of state was captured in a late-night U.S. military raid — and whether that affects the legitimacy of their case.
Additionally, Maduro is expected to argue that as leader of Venezuela, he should be shielded from prosecution, according to Stephen Vladeck, a professor at Georgetown Law who specializes in federal courts and national security law.
"Just about every country recognizes this doctrine called the head of state immunity, which is the idea that one country doesn't prosecute [a current or] prior head of state of another country for crimes they committed or alleged crimes they committed while they were head of state."
But Vladeck says Maduro's case is special.
"The tricky part is that the question of whether someone's the head of state turns, at least to some degree, on diplomatic recognition, on whether the country that's trying to bring in the prosecution, recognizes that individual as the head of state," he said.
As a result of this complexity of the case, it's likely to drag on, Vladeck said: "The pretrial proceedings alone, I think, are going to take a fair amount of time. We're talking years, not months."
The potential for a lengthy trial has sparked questions and concerns in the media about Judge Hellerstein's age.
But people who have worked with Hellerstein or appeared before him in court say: Don't count him out.
Shira Scheindlin, who served as a U.S. District Court judge in the Southern District of New York at the same time as Hellerstein, said: "Any judge of that age has to self-assess. And so they should make their own careful decision as to whether they really feel they should do it. Knowing [Hellerstein], I trust he will make the right decision."
Hellerstein's path to the bench
Hellerstein, who was appointed to the bench by then-President Bill Clinton in 1998, is widely seen as thoughtful, methodical and probing.
He attended Columbia College and Columbia Law School and served as a law clerk to the U.S. District Judge Edmund L. Palmieri, who served in the Southern District of New York. He also served in the Judge Advocate General's Corps of the U.S. Army, more commonly known as JAG.
He didn't respond to NPR's requests for an interview for this story.
Hellerstein is an Orthodox Jew and has said that he faced religious discrimination early in his legal career. In a 2020 interview for the podcast Behind the Bima, Hellerstein said "as a Jewish boy [interviewing] at law firms, you met up with very strong discrimination — some of it overt, much of it implied."
He continued: "Even joining a Jewish firm caused you to lose face. You got less pay; Jewish firms worked on Saturdays. They paid their employees on Saturdays. … I told the partners that interviewed me that I would not work on Shabbat, except for emergencies."
Judge Hellerstein said that advocacy helped. "They decided to take me. I was the first Orthodox boy employed by a Gentile or Jewish firm in New York City," he said.
Before taking the bench, he spent decades as a lawyer at the now-shuttered firm Stroock & Stroock & Lavan, where Scheindlin once worked. "He was my first boss at the law firm," when she was a brand-new associate in the litigation department, Scheindlin said.
"He was considered a very good boss, very smart, very experienced," and he offered to share that experience with his subordinates, Scheindlin said. He was open to working with the young lawyers to improve their work, she said, "So you learned a lot."
In 1998, when he joined the Southern District, where she was already on the bench, the roles reversed.
"I was sort of his tutor," she said.
In speaking of Hellerstein, Scheindlin describes a jurist who approaches the law with rigor, which she says will be useful for the Maduro trial.
"The world is watching. He's going to be very thoughtful, very careful, very prepared, as he always is," she said. "Every issue will be well-researched and well-reasoned."
But the former judge acknowledged that there are particular challenges that may arise during the Maduro trial. "You really have to think hard to get these people the right outcome [because] there's no guidance in prior precedents," she told NPR.
"It's also challenging because of the media scrutiny that it will draw up. There's going to be an article every minute once there's hearings or motions or trials," she added. "Every word you say or write will be scrutinized. You're under a microscope."
Hellerstein's experience as a federal judge
Hellerstein has spent decades handling high-profile cases.
He is well-known for presiding over 9/11-related lawsuits, including those filed by victims' families, first responders and others. In one of his largest cases, involving dozens of victims' families, and to help handle the complexity and volume of this litigation, Hellerstein appointed a special master named Sheila Birnbaum.
That sticks out to Scheindlin, who said, "That was pretty cool because most judges are always appointing men. I think he was conscious of doing right by women."
He also appeared conscious of doing right by the plaintiffs. Some had turned to the judge to ask him whether they should take a settlement after years of litigation.
In a 2016 New York Times article, Hellerstein said, in a rare media interview, "I thought it was very important that there be a sense of equity, that people be satisfied as best they could be satisfied in such tragic circumstances."
Ultimately, the cases were settled out of court.
In one long-running Freedom of Information Act case brought by the American Civil Liberties Union, Judge Hellerstein had to balance national security concerns with public transparency, Alex Abdo said.
In 2004, after filing multiple requests for records relating to allegations of abuse and torture of prisoners in U.S. detention centers overseas, the ACLU sued the Department of Defense and other federal agencies.
Abdo, who is now the litigation director of the Knight First Amendment Institute at Columbia University, joined the ACLU on this case, in its early stages, around 2005.
The litigation went on for more than a decade.
The U.S. government argued against the release of the pictures from Abu Ghraib and other military detention facilities in Iraq and Afghanistan taken by U.S. Army personnel. The government claimed the images of the abuse must stay hidden to avoid fueling insurgents and anti-U.S. sentiment, which would put the lives of troops in even more danger during the Iraq War, they claimed.
Abdo said Hellerstein came across as "very methodical" and not driven by ideology, while balancing the case.
"He did hold the government's feet to the fire," Abdo said, crediting him with forcing disclosures that ultimately produced thousands of pages of documents, including the notorious government torture memos.
Many times in this case, Hellerstein deferred to government claims about national security concerns as the ACLU fought for the release of more records, Abdo said, but the judge made clear there were limits.
In one of his opinions in this long-running case, Hellerstein expressed frustration about the government's excuses for not handing over the complete set of records he had ordered them to release.
Hellerstein wrote, "To give in to fear of our enemies, their propaganda, or their blackmail, is to surrender some of our dearest held values … it remains the case that our nation does not surrender to blackmail, and fear of blackmail is not a legally sufficient argument to prevent us from performing a statutory command."
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