In the heart of Manhattan's federal courthouse, a 92-year-old judge with a storied career is presiding over one of the most high-profile trials in recent U.S. history: the case against former Venezuelan President Nicolás Maduro. U.S. District Judge Alvin K. Hellerstein, an Orthodox Jew who has served on the bench for nearly three decades, opened proceedings on Monday by emphasizing his commitment to a fair trial for Maduro, who pleaded not guilty to narco-terrorism charges. "That's my job, and that's my intent," Hellerstein told the courtroom, according to Reuters reporting.
Hellerstein's chambers bear a prominent display of a Hebrew scripture from the Torah: “Tzedek, tzedek tirdof” — translated as “Justice, justice you shall pursue.” This inscription reflects the judge's deeply held Jewish values, which he has openly discussed as influencing his judicial philosophy. In a 2013 law review article, Hellerstein wrote, "As a judge, and as a Jew, I consider that everything I do reflects God and affects His image." His faith extends to practical aspects of his role; in a 2020 podcast, he revealed that he deliberately schedules sentencing hearings for Fridays, allowing time during Shabbat — the Jewish sabbath from Friday sunset to Saturday nightfall — to contemplate the appropriateness of the sentences he imposes.
The Maduro trial, unfolding in the Southern District of New York, accuses the ousted leader and several associates of leading a criminal enterprise that allegedly conspired with Colombian rebels to flood the United States with cocaine. Maduro, who was captured in Venezuela last year amid political upheaval, faces charges that could result in decades behind bars if convicted. Prosecutors from the U.S. Department of Justice have described the operation as a narco-terrorism plot, while Maduro's defense team has argued that the case is politically motivated, tied to U.S. efforts to undermine his regime.
Hellerstein's selection to oversee the case draws attention not just for its gravity but for his reputation as a judge unafraid to challenge powerful figures. Over the years, he has repeatedly ruled against former President Donald Trump and his administration in several notable disputes. In 2020, Hellerstein ordered the release of Michael Cohen, Trump's former personal lawyer, from prison after the Justice Department under Trump attempted to revoke his home confinement. The judge concluded that the move was retaliatory, stemming from Cohen's plans to write a book critical of the president. "This is retaliation," Hellerstein stated at the time, according to court records.
More recently, in 2023, Hellerstein denied Trump's request to transfer his New York state criminal case involving hush money payments to adult film actress Stormy Daniels to federal court. Trump was ultimately tried in state court and convicted on 34 felony counts related to falsifying business records. Hellerstein's decision underscored his view that the case belonged in the state jurisdiction, rejecting arguments from Trump's legal team about federal involvement.
In May 2025, Hellerstein made headlines again by blocking the Trump administration's attempt to deport alleged Venezuelan gang members using a wartime law from World War II. The judge ruled that the men had been improperly denied due process, criticizing the government's reliance on tattoos as evidence of gang affiliation. “This is the United States of America," he declared during the hearing. "People are being thrown out of the country because of their tattoos.” The ruling highlighted Hellerstein's emphasis on constitutional protections, even in cases involving national security concerns.
Beyond his clashes with Trump, Hellerstein's tenure includes landmark decisions in other major cases. In 2013, he rejected a $675 million settlement between New York City and injured first responders from the September 11, 2001, attacks at the World Trade Center. Lawyers for the victims and the city had negotiated the deal, but Hellerstein deemed it inadequate, invoking his inherent authority as a judge to demand better terms despite no explicit statute requiring his approval. Some attorneys expressed outrage, accusing him of "arrogation of power," as Hellerstein later recounted in his 2013 article. Ultimately, the parties returned with an improved settlement that added $125 million for the victims.
Mitchell Epner, a former federal prosecutor who has observed Hellerstein in action, described the judge as "a man of strongly held convictions and he seeks to find a way to harmonize the law with his understanding of justice." Epner's assessment aligns with Hellerstein's own reflections on his career, which began long before his federal appointment. Nominated to the bench by President Bill Clinton in 1998 and confirmed that year, Hellerstein had already built an extensive legal resume.
From 1957 to 1960, Hellerstein served in the Judge Advocate General's Corps, the U.S. Army's legal branch, handling military justice matters during the tail end of the Korean War era. After leaving active duty, he joined the prominent New York firm Stroock & Stroock & Lavan in 1960, where he practiced law for much of his professional life until the firm's dissolution in the early 2000s. Hellerstein has proudly noted his trailblazing role as an Orthodox Jew in the legal field. In the 2020 podcast, he said, "I'm pleased to say that after me there were others, and some credited me with having broken the precedent." He believes he was "the first Orthodox boy employed by a gentile or Jewish firm in New York City."
Hellerstein's approach to judging extends to his interactions with attorneys. He has been known to intervene when he feels lawyers are not adequately representing their clients, a stance that has sometimes drawn criticism but also praise for prioritizing fairness. In the Maduro case, this philosophy could play a pivotal role, as the defense has already signaled plans to challenge the validity of evidence obtained during Venezuela's political transition.
The trial's opening on Monday in Manhattan's Daniel Patrick Moynihan U.S. Courthouse set the stage for what prosecutors expect to be a months-long proceeding, with witness testimonies from former Venezuelan officials, DEA agents, and international experts. Maduro, appearing via video link from detention, maintained his composure during the plea, surrounded by a team of U.S.-based lawyers experienced in international extradition cases. While the Venezuelan government has condemned the proceedings as an "illegal kidnapping," U.S. officials insist the charges are based on years of investigation into Maduro's alleged ties to the Revolutionary Armed Forces of Colombia (FARC).
As the case progresses, Hellerstein's background may influence how he navigates complex issues like the admissibility of foreign-sourced evidence and the balance between national security and individual rights. Legal observers note that his history of independent rulings positions him well for a trial rife with geopolitical undertones. Epner added that Hellerstein's courtroom demeanor is deliberate and thoughtful, often pausing to ensure all parties are heard.
Looking ahead, the Maduro trial could have ripple effects on U.S.-Latin American relations, particularly as Venezuela grapples with its post-Maduro transition under interim leadership. If convicted, Maduro's sentence could be handed down in late 2025 or early 2026, giving Hellerstein another opportunity to reflect during Shabbat on the scales of justice. For now, the judge's Torah-inspired ethos serves as a quiet reminder in his chambers of the pursuit that defines his long career.
Hellerstein's defiance of executive overreach, from Trump-era policies to earlier settlements, underscores a judiciary committed to checks and balances. In an era of polarized politics, his steady hand offers a model of impartiality, even as the Maduro case tests the boundaries of international law and accountability.