The 92-year-old judge overseeing the Nicolas Maduro case has said he displays a Hebrew scripture from the Torah on the wall of his Manhattan chambers: “Tzedek, tzedek tirdof” — “Justice, justice you shall pursue.”

An Orthodox Jew who has been on the bench for almost three decades, U.S. District Judge Alvin Hellerstein has been outspoken about how he tries to promote fairness and the impact of his faith on his judicial philosophy.

Hellerstein opened the court hearing on Monday by saying he wants a fair trial for the ousted Venezuelan leader, who pleaded not guilty on Monday to narco-terrorism charges.

“That’s my job, and that’s my intent,” Hellerstein said.

On the Seventh Day He Contemplates

Hellerstein said in a 2020 podcast that he schedules sentencing hearings for Fridays, so that he can spend Shabbat — the Jewish sabbath from Friday sunset to Saturday nightfall — reflecting on whether the prison sentence he handed down was appropriate.

Hellerstein has ruled against President Donald Trump in recent years. He has also spoken up when he believes lawyers are not best serving their clients.

In a 2013 law review article, he wrote that some lawyers were “outraged” and accused him of “arrogation of power” when he rejected a $675 million settlement negotiated between New York City and injured first responders who raced to the World Trade Center after the attacks of September 11, 2001.

Hellerstein concluded that, while no statute or rule clearly addressed whether the deal needed his blessing, he had inherent authority to reject it as inadequate.

The attorneys ended up presenting Hellerstein with a new settlement that added $125 million for victims.

Hellerstein “is a man of strongly held convictions and he seeks to find a way to harmonize the law with his understanding of justice,” said Mitchell Epner, a former federal prosecutor who has observed Hellerstein on the bench.

Hellerstein has spoken candidly about how his Jewish values affect his decision-making.

“As a judge, and as a Jew, I consider that everything I do reflects God and affects His image,” he wrote in the 2013 article.

In the 2020 podcast, Hellerstein said he believes he was “the first Orthodox boy employed by a gentile or Jewish firm in New York City.”

“I’m pleased to say that after me there were others, and some credited me with having broken the precedent,” Hellerstein said.

Hellerstein already had a long career before President Bill Clinton nominated him to the federal bench in 1998.

From 1957 to 1960, Hellerstein served in the Judge Advocate General’s Corps, the legal arm of the United States Army.

In 1960, Hellerstein joined the now-defunct firm of Stroock & Stroock & Lavan, where he ended up practicing for much of his career.

A History of Rebuking Trump’s Legal Gambits

In a high-profile case in 2020, Hellerstein ordered the release of former Trump personal lawyer Michael Cohen, after Trump’s Justice Department tried to revoke his home confinement and return him to jail.

Hellerstein concluded Trump’s administration was retaliating against Cohen for writing a book.

In 2023, Hellerstein denied a request by Trump to move to federal court his New York criminal case relating to a hush money payment to adult film actress Stormy Daniels. Trump was tried in state court and found guilty of 34 felony counts.

In May 2025, Hellerstein rejected an effort by the Trump administration to use a wartime law to send alleged gang members to Venezuela, saying the men had been improperly denied their day in court.

“This is the United States of America,” he said. “People are being thrown out of the country because of their tattoos.”

—

(Reporting by Jan Wolfe; Editing by Noeleen Walder and Howard Goller)