Maduro Case Judge, 92, Brings History of Dealing With Trump

The judge overseeing the Nicolás Maduro prosecution is a 92-year-old native New Yorker who’s willing to take unpopular stances, is unafraid to challenge lawyers, and has managed to win praise from President Donald Trump despite crossing him on key issues.

“He doesn’t reflexively rule for the government,” said Roger Stavis, the head of Mintz & Gold’s white collar defense practice, who’s tried cases before Manhattan US District Judge Alvin Hellerstein.

“My test for a fair judge is: I could be disappointed in a ruling, but if I know the judge thought it was the right ruling, I can’t complain. I complain if the judge knows the right ruling but doesn’t rule that way for politics or some other reason. He passes that test.”

A Bronx native and Columbia Law School graduate, Hellerstein’s shown an independent streak through a series of administrations since his 1998 appointment by President Bill Clinton.

That’s included siding against Trump, who ordered the operation capturing the Venezuelan president who’s now a defendant in Hellerstein’s courtroom. Maduro pleaded not guilty to narco-terrorism conspiracy, cocaine importation, and machine gun charges on Monday.

Hellerstein in April denied the Trump administration’s bid to deport alleged Venezuelan gang members, saying detainees facing removal under the Alien Enemies Act had to get notice and an opportunity to challenge their deportations before they’re flown out of the country.

“He’s a real believer in due process,” said New York County Lawyers Association President Richard Swanson. “He’s not going to be swayed by politics. If anything, Maduro should be glad he has a fair judge.”

Talking to reporters aboard Air Force One on Sunday, Trump said: “The judge is very respected. We’ll see how we do,” adding “we’re going to go through a slog of a trial.”

Hellerstein, who declined an interview request on Monday, twice denied Trump’s bid to get the criminal “hush money” case against him into federal court. The judge said Trump failed to show that payments to Stormy Daniels were part of his official duties as president.

“The evidence overwhelmingly suggests that the matter was a purely a personal item of the President — a cover-up of an embarrassing event,” Hellerstein ruled in 2023.

That case is back before Hellerstein now after the Second Circuit ruled the judge didn’t properly consider the US Supreme Court ruling giving presidents broad immunity from criminal charges.

Immigrant Parents, Public School

Hellerstein’s reputation as a judge was built partly through overseeing a trove of litigation against airlines and New York City related to the 9/11 attacks.

In 2010, he rejected a settlement to resolve suits brought against the city by rescue and cleanup workers who said they were sickened at Ground Zero, saying the amount was too small. (He later approved a $712.5 million settlement.)

Hellerstein said in a Touro Law Review article that rejecting the settlement was a controversial move, and reflected on how his upbringing and religion have shaped him.

Hellerstein wrote that he would “not want it to be said that I ruled in a certain way because I am an Orthodox Jew.” But he said his rulings reflect “all that influenced me,” including “my immigrant parents, my growing up in the Bronx, my public school education,” service in the Judge Advocate General corps, and “my Jewish education and my Jewish values.”

In a separate case, Hellerstein ruled against families seeking to recover human remains from the 9/11 debris. Norman Siegel, the former head of the New York Civil Liberties Union, who represented the families, said Hellerstein impressed him by setting up a meeting in his chambers with the families to hear them out.

“Even though he didn’t rule for us, he spent over an hour listening to them, and understanding their loss, their anger, and trying to explain to them the limits of the law,” Siegel said. “Not many judges would do that.”

Hellerstein ruled in Siegel’s favor in a 1999 decision, later reversed by the Second Circuit, saying Ku Klux Klan members had a free expression right to march in masks. “He believed in the rights of the quintessential, unpopular, controversial group,” Siegel said.

‘Jury Looks Bored to Tears’

Hellerstein recently oversaw high-profile financial trials: the Charlie Javice case, the prosecution of Archegos founder Bill Hwang, and a trial against BNP Paribas.

In those cases, Hellerstein showed he likes to move things along and will let lawyers know.

“The jury looks like it’s bored to tears,” Hellerstein remarked to attorneys at the 2024 Archegos trial. “I think you should stick to what’s important, please.”

He wasn’t having it at the BNP Paribas trial when an attorney took issue with Hellerstein’s remembrance of Sept. 11.

That case, in which Sudanese refugees accused BNP Paribas of aiding human-right abuses, kicked off on Sept. 11, 2025. The bank’s attorney, Barry Berke, argued the judge’s invocation of the 9/11 attacks could bias jurors and, later in the day, moved for a mistrial.

“I heard nothing objectionable,” Hellerstein said. “If you thought it was objectionable, you should have stood up.”

Hellerstein showed another side of himself during Javice’s September sentencing, seeming to take into account testimony concerning her good character.

The government asked for 12 years after Javice, then 33, was convicted of defrauding JPMorgan Chase & Co. in its $175 million acquisition of her student-finance startup Frank. Hellerstein gave her seven.

The judge told Javice she’d done a bad thing that required punishment, but added, “You’re a good person.”