Alvin Hellerstein was 64 years old when former President Bill Clinton appointed him to the federal bench. That was more than a quarter century ago. Now, the 92-year-old senior judge in the U.S. District Court for the Southern District of New York adds former President Nicolás Maduro to his roster of prominent, famed and infamous defendants — but he's not the first former head of state to come before Hellerstein's court.

Hellerstein has repeatedly rejected efforts by President Trump to remove his New York State criminal case to federal court, penning withering criticisms of Mr. Trump's arguments that the facts at the heart of his "hush money" case warranted official acts conducted during his first presidency. Mr. Trump was found guilty by a state jury in that case, which revolved around reimbursements made to a former Trump attorney, Michael Cohen, for a payment just before the 2016 presidential election to adult film star Stephanie Clifford, whose stage name is Stormy Daniels. 

"Reimbursing Cohen for advancing hush money to Stephanie Clifford cannot be considered the performance of a constitutional duty," Hellerstein wrote. "Falsifying business records to hide such reimbursement, and to transform the reimbursement into a business expense for Trump and income to Cohen, likewise does not relate to a presidential duty."

But a 2024 ruling by the Supreme Court has forced Hellerstein to reconsider that determination. The U.S. Court of Appeals for the Second Circuit ordered Hellerstein to reexamine arguments around presidential immunity, factoring the Supreme Court's landmark decision that upended multiple Trump cases.

Hellerstein was also the judge assigned to preside over an American Civil Liberties Union effort that challenged the deportation of two Venezuelans last year. Hellerstein granted a temporary restraining order protecting deportees in the Southern District of New York from being removed prior to receiving due process. The case was filed on behalf of two Venezuelans challenging the use of the Alien Enemies Act to deport alleged gang members.

The no-nonsense judge also recently presided over the 2025 trial of Charlie Javice, who was convicted of defrauding JPMorgan Chase out of $175 million by lying about the size of her company's customer base. That company, Frank, claimed to revolutionize the way college students applied for financial aid.

Hellerstein has presided over matters tied to the Maduro case since 2014 when he was assigned to a related case. He oversaw a superseding indictment naming Maduro in 2020. Monday's hearing was, of course, the first time the lead defendant has appeared in Hellerstein's court.