(NEW YORK) — As Venezuelan President Nicolas Maduro and his wife were arraigned this week on narco-terrorism charges, the key legal players in the case included a 92-year-old judge and the attorney for WikiLeaks founder Julian Assange.

The case with international implications will feature high-profile defense attorneys and will be presided over by the most senior U.S. District Court Judge for the Southern District of New York.

Maduro and his wife, Cilia Flores, on Monday pleaded not guilty to federal drug trafficking charges. The next court date is set for March 17.

The Judge

U.S. District Court Judge Alvin Hellerstein was appointed to the federal bench in 1998 by former President Bill Clinton and was confirmed by the Senate through unanimous consent.

Known by colleagues and lawyers as a no-nonsense jurist with an independent streak, Hellerstein presided over the 2019 federal civil trial of Harvey Weinstein, brought by 16 women who accused the former movie mogul of sexual assault.

In a major July 2020 ruling, Hellerstein, who turned 92 last month, tossed a $19 million settlement in the Weinstein civil case, saying that it failed to adequately compensate the accusers.

In his decision, Hellerstein slammed the settlement proposal as unfair, noting that accusers who had merely met Weinstein would receive compensation equal to those who were allegedly sexually assaulted by him.

“What is there to make me believe that a person who just met Harvey Weinstein has the same claim as the person who is raped by Harvey Weinstein?” the judge asked during a hearing on the settlement. 

Additionally, the judge said it was “obnoxious” that the settlement proposal would have included money to cover the legal fees for Weinstein and other directors of his former company. 

Hellerstein has also ruled against President Donald Trump, whose Justice Department is prosecuting Maduro, in multiple instances.

In 2023 and 2024, Hellerstein rejected requests by Trump’s attorneys to move a case charging him with falsifying business records to hide hush-money payments to adult movie star Stormy Daniels from state court to federal court.

“Trump has failed to show that the conduct charged by the Indictment is for or relating to any act performed by or for the President under color of the official acts of a President,” Hellerstein wrote in his ruling.

Trump was eventually convicted in state court on 34 felony counts.

In April 2025, Hellerstein blocked the Trump administration from deporting migrants under the Alien Enemies Act, ruling that migrants being held in the Southern District of New York could not be deported without them first receiving notice and an opportunity for a hearing.

Maduro’s attorney

Barry Pollack, Maduro’s attorney, has more than 30 years of experience as a lawyer and has represented high-profile clients. 

During Maduro’s arraignment on Monday, Pollack signaled that that he could assert that he is entitled, as a foreign leader, to protection against prosecution.

“He is the head of a sovereign state,” Pollack said in court, adding that there are “issues about the legality of his military abduction.”

Among the attorney’s past clients is Julian Assange. In June 2024, Pollack negotiated a plea agreement for the WikiLeaks founder who was charged with violating the Espionage Act for publishing classified information he obtained from Chelsea Manning, a U.S. Army intelligence analyst.

Under the plea agreement that Pollack hammered out with the Department of Justice, Assange was freed from prison in June 2024 after pleading guilty to a single felony count of conspiring to unlawfully obtain and disseminate classified information.

Pollack — a partner in the Harris St. Laurent & Wechsler law firm in New York City and Washington, D.C. — also won the freedom of Martin Tankleff, a Long Island, New York, teenager who was wrongfully convicted of murdering his parents in 1988. Tankleff was released from prison in 2008 after Pollack successfully filed an appeal, arguing there was insufficient evidence to convict him.

Pollack also defended Michael Krautz, former accountant for the Enron Corp., who was charged along with other company executives with fraud and conspiracy to falsify business records stemming from overstated earnings of the company’s now-defunct subsidiary Enron Broadband Services.

Krautz was acquitted of the charges in 2006, just days after Enron founder Kenneth Lay and CEO Jeffrey Skilling were convicted on similar charges in one of the biggest business scandals in U.S. history.

“Barry’s unwavering commitment to his clients, the defense function, and the Constitution serves as inspiration to criminal defense lawyers across the nation,” Christopher W. Adams, president of the National Association of Criminal Defense Lawyers, said in 2021, as the organization honored Pollack with its Robert C. Heeney Memorial Award.

Maduro also added constitutional law expert Bruce Fein to his legal defense team, according to a notice on the court docket on Tuesday. Fein has written critically about the Trump administration’s deportation policies and the president’s use of pardons.

Maduro’s wife’s lawyer

Houston-based defense attorney Mark Donnelly, a former federal prosecutor, has been retained by Maduro’s wife, Cilia Flores.

Donnelly is the former senior advisor to the U.S. Attorney for the Southern District of Texas and was a federal prosecutor for 12 years before going into private practice. He is now a partner in the Houston law firm Parker Sanchez & Donnelly.

“With over 100 jury trials under his belt, Mark not only is extremely comfortable in the courtroom, but also has the knowledge and experience to guide clients through all phases of representation,” his bio on his law firm’s website says.

According to the bio, Donnelly spent eight years as a prosecutor in the Harris County, Texas, District Attorney’s Office, where he led investigations into elected officials and others charged with violating the public trust.

In 2023, the Texas House of Representatives recruited Donnelly to assist in the historic investigation and impeachment trial of then-state Attorney Gen. Ken Paxton, who was accused of bribery and abusing his office to protect a donor accused of making false statements to secure business loans.

Paxton, a Republican, was acquitted in September 2023.

Donnelly is a proficient Spanish speaker and was once designated as a bilingual assistant prosecutor for the Harris County District Attorney’s Office.

“We look forward to reviewing and challenging the evidence the government has,” Donnelly said in a statement to Houston Public Media about representing Flores. “While we would love to present our side now, we will wait to do so in court at the appropriate time. The first lady is aware that there is a long road ahead and is prepared.”

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