In a guest essay for The New York Times published on Tuesday, lawyer and author Jeffrey Toobin argued that the judge overseeing President Nicolás Maduro’s trial should step aside, citing his advanced age and an incident during a 2025 trial in which he was reportedly caught falling asleep during proceedings.
Toobin, who was fired from The New Yorker in 2020 after exposing himself on a Zoom call with colleagues, explained that the best way for Judge Alvin K. Hellerstein to “honor the system to which he has devoted decades of his life” would be to withdraw from the incredibly high-profile case.
In addition to Hellerstein’s age—the judge is 92 years old—Toobin cited instances in which he fell asleep while presiding over the six-week trial of Charlie Javice, a 32-year-old CEO who was convicted of defrauding JPMorgan Chase of $175 million.
As Toobin explains, Javice’s lawyers are seeking a new trial in part because “during trial, at least one newspaper article reported that the presiding judge was sleeping, at times, during the proceedings.”
A February 2025 article from ArtVoice noted that Hellerstein “was observed nodding off at one point during the proceedings.”
One person familiar with the case told Toobin that the prosecution and defense conferred on how to handle Hellerstein’s impromptu naps, but ultimately decided not to take any action, so as not to risk offending him.
Toobin argues that Maduro’s case, which will see him tried for a series of charges including narco-terrorism, cocaine importation, and possession of weapons—all after being kidnapped by U.S. military forces from his palace in Venezuela—is far too complex, and high-profile, to risk being overseen by a nonagenarian judge with a history of falling asleep during proceedings.
Toobin also highlights the lack of a procedural mechanism that would enable people to challenge the fitness of judges; instead, what usually happens is that peers gently encourage judges to step aside. In this case, Toobin says, Chief Judge of the Southern District of New York Laura Taylor Swain should suggest Hellerstein step aside if he does not do so on his own.
Hellerstein was appointed in 1998 by then-President Bill Clinton, and became a senior judge in 2011. Politico noted on Monday that he has ruled against the Trump administration in several high-profile cases, including rejecting President Donald Trump’s bids to have his fraud case moved to federal court. Trump was later convicted on 34 felony counts of falsifying business records.
Last May, Hellerstein also blocked the administration’s attempts to use the Alien Enemies Act to deport immigrants in the Southern District of New York.
Maduro has already appeared in front of Hellerstein once, entering the court in shackles on Monday after his abduction on Saturday and referring to himself as the “still president of Venezuela.”
Maduro told the court that he had been kidnapped and was a prisoner of war. He also stated his innocence, telling the court, “I’m innocent. I’m not guilty. I am a decent man.”
As Toobin noted, the case is so complicated that Hellerstein did not schedule the next conference until March 17, at which point the parties will address the hearing schedule.
“It’s almost inconceivable that a trial will begin until 2027, when Judge Hellerstein will be 93,” Toobin writes. “The trial itself will then last many months, with the judge called upon to decide additional highly consequential issues under enormous public scrutiny.”
“For Judge Hellerstein to hang on to the Maduro case when he will be well into his 10th decade would be a disservice to himself, to the parties in court, and to the cause of justice in America.”
The Daily Beast reached out to the United States District Court’s Southern District of New York for comment.
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