Alvin K. Hellerstein, a Manhattan federal judge who handled prominent cases involving President Donald Trump, former Venezuelan President Nicolás Maduro and the 9/11 terror attacks across nearly three decades on the bench, has died at 92.

Chief Judge Laura Taylor Swain made the announcement on Wednesday, remarking that his “energetic and dedicated service to this Court continued until his death.”

She added, “He is greatly appreciated and will be sorely missed.”

Appointed to the federal bench in 1998 by President Bill Clinton, a Democrat, Hellerstein kept a robust docket and worked until his death.

Just two weeks ago, he presided over the arraignment of Maduro and Maduro’s wife, Cilia Flores, on torture charges that were added to their ongoing narco-terrorism conspiracy case.

Maduro, who was captured alongside his wife earlier this year in a surprise U.S. military raid in Caracas, twice defied Hellerstein’s request that he enter a plea to the charges.

Annoyed, Hellerstein took matters into his own hands, interjecting that “a plea of not guilty will be entered on behalf of Mr. Maduro.”

At Flores’ Oct. 8 bail hearing, Hellerstein coughed and struggled to speak at times, telling lawyers, “I have a voice problem. As long as you can understand, hear me, I’ll keep going.”

Nevertheless, he was resolute that he’d preside over Maduro and Flores’ trial, which he’d scheduled for next June.

In August, in one of his last significant rulings, Hellerstein again spurned Trump’s effort to erase his hush money conviction, rejecting the president’s bid to move the state court case to federal court and have it dismissed on presidential immunity grounds.

It was the third time Hellerstein denied Trump’s requests to move the case.

The first time was after Trump’s March 2023 indictment; the second followed Trump’s May 2024 conviction and a subsequent U.S. Supreme Court ruling that presidents and former presidents cannot be prosecuted for official acts.

Hellerstein’s latest ruling against Trump came after an appeals court ordered him to reconsider his prior decision. The 2nd U.S. Circuit Court of Appeals ruled that Hellerstein erred by failing to consider “important issues relevant” to the president’s request. However, the appeals court judges said they “express no view” on how Hellerstein should rule.

In 2020, Hellerstein ordered Trump’s estranged former lawyer and fixer Michael Cohen released from prison after the Justice Department revoked his home confinement to thwart his efforts to publish a book or talk to the media. The government’s action, he ruled, was retaliatory and a First Amendment violation.

In the aftermath of the 2001 terror attack on the World Trade Center, Hellerstein presided over dozens of wrongful death, injury and property damage lawsuits — a two-decade-long effort that shaped his legacy on the bench.

Some of the judge’s former clients died in the attack and, lawyers say, he showed great empathy to victims and their families, meeting with them for hours in his chambers and rejecting what he felt were low-ball settlement offers.

In March 2010, Hellerstein rejected as insufficient a settlement that would have paid at least $575 million to thousands of people who fell ill working in the toxic ash of the trade center. He acknowledged he was breaking with tradition by getting so involved in the case.

“Most settlements are private. A plaintiff and defendant come together, shake hands, and it’s done with,” he explained. The judge usually has no part in saying yes or no.

“This is different,” Hellerstein said. “This is 9/11.”

Others were dismayed when, in 2008, Hellerstein ended an effort to force New York City government to keep searching for human remains in debris moved from Ground Zero to a Staten Island landfill.

His other notable recent cases included the criminal trials of Charlie Javice, who was convicted last year of defrauding JPMorgan Chase out of $175 million by exaggerating the customer base for her financial aid startup, and hedge fund founder Bill Hwang, who was convicted in 2024 of securities and market manipulation fraud in a scheme that cost banks billions of dollars.

He also presided over a 2025 civil trial at which a jury ordered French bank BNP Paribas to pay nearly $21 million for giving the Sudanese government access to the U.S. financial system as it engaged in atrocities two decades ago.

Hellerstein also made headlines in 2015, when he ordered a New York City cable company to pay a Texas woman $229,500 for flooding her phone with 153 robocalls.

Hellerstein, known for a quirky independent streak and strict discipline in his courtroom, insisted spectators wear pandemic-era masks for more than two years after other judges stopped the practice.

He was a federal district judge until he moved to senior status in 2011. Before that, Hellerstein served in the U.S. Army Judge Advocate General’s Corps and was a Manhattan litigator.