Every Assistant U.S. Attorney in the Southern District of New York has that one judge he just can’t escape.
Although cases are assigned randomly through a process that combines bingo with the NBA draft lottery – sealed envelopes containing index cards, each bearing the name of one of the forty or so district court judges, drawn randomly from a hollow wooden wheel – every new prosecutor somehow finds that seemingly half his cases somehow wind up with one particular judge. For me, that judge was Alvin K. Hellerstein – the same man who now presides over the Nicolas Maduro case and, through a combination of inaction and irrationality, threatens to waylay the prosecution.
I don’t relish writing this. Judge Hellerstein is a good man, well-intentioned and generally amiable. I did fine in his courtroom, and there’s plenty more good blood between us than bad. But he’s simply not up for the job of presiding over the single most important criminal case currently pending in our federal court system.
Judge Hellerstein took the bench in 1998, upon nomination by Bill Clinton. He’s held “senior” judicial status since 2011, which means he carries a reduced caseload. The Judge is now 92 years old. He was born in December 1933; he was eleven when World War II ended, 29 when JFK was assassinated, and 41 when the Vietnam War ended. Judge Hellerstein reportedly fell asleep on the bench at times during his most recent trial, last year. When I practiced in his courtroom in the mid-2000s and early 2010s, he was in his 70s. He was capable then, but at times displayed spotty judicial decisionmaking.
Too often, Judge Hellerstein rules by gut instinct, without regard for the law. As Politico delicately phrased it, the Judge is renowned among practitioners for his “stubborn streak” and “an often unorthodox approach to running his courtroom.” As one personal example, he made an obvious legal error in a gun case of mine that was about to go to trial. I filed a brief explaining why he was plainly wrong, but he never read it. He ruled against the prosecution anyway, and got reversed unanimously by the Court of Appeals, which noted pointedly that the Judge’s legal rationale had previously been “rejected by this [appellate] court without equivocation.”
When the Maduro indictment was wheeled out randomly to Judge Hellerstein in early January 2026, he could have reassigned it. Senior judges sometimes do this with cases that promise to be drawn-out and demanding, but the Judge kept the case for himself. That fateful decision already has had troubling consequences.
First, the Maduro case is moving along at an exasperating pace for all involved. District judges hold virtually unfettered power to set schedules, and a judge who understands the necessity for a prompt resolution can typically move from indictment to trial in a year or less. Yet nearly four months in, the Maduro case is essentially nowhere. Forget about a trial date – the Judge hasn’t yet even set a definitive schedule for pre-trial motions. At this pace, there’s no chance of a 2026 trial, and even 2027 might be a stretch. (Judge Hellerstein appears to be a magnet for high-profile case assignments; he also has a piece of the appeal of Donald Trump’s hush money conviction. Nearly six months ago, the Court of Appeals ruled that the Judge had not “adequately considered issues relevant to the [case]” and sent the matter back to him for reconsideration. He hasn’t ruled yet.)
Judge Hellerstein now stands on the brink of a precipitous decision that could undermine the Maduro prosecution and potentially set the case back to its starting point. In March, the Judge held a hearing to determine whether Maduro’s legal fees could be paid by the country of Venezuela. Maduro’s private defense team – which likely will accrue fees in the millions of dollars – argued that Venezuela is willing to pay, and that Maduro’s constitutional right to counsel would be compromised by a decision barring such funding. The Justice Department countered that economic sanctions imposed by the U.S. government against Venezuela and Maduro prohibit such payments, and that Maduro should be not permitted to use “plundered” assets to fund his criminal defense.
At the hearing, the Judge seemed distinctly inclined in Maduro’s favor. He questioned the wisdom of the U.S. government’s sanctions: “What is the interest of the government now in blocking those funds? We are doing business in Venezuela.” And he noted that, “The defendant is here; Flores [Maduro’s wife] is here. They present no further national security threat.” Judge Hellerstein concluded the hearing without ruling, and promised to issue a decision soon. (Nearly a month later, he hasn’t ruled yet.)
If Judge Hellerstein allows Venezuela to fund Maduro’s defense, he’ll put the Justice Department in a bind. On one hand, prosecutors could accept such a ruling, incorrect though it would be. Judge Hellerstein plainly misunderstands (or oversimplifies) the purpose of sanctions. He seems to think they’re based on whether a person poses “a national security threat” when in fact sanctions can be about much more: international diplomacy, politics, economics, and trade. Moreover, under basic Constitutional principles, sanctions are within the purview of the Executive and Legislative Branches, not the Judiciary. It takes breathtaking arrogance for any district judge to purport to unilaterally overturn the will of the President and Congress on matters of foreign affairs and international relations.
Or the Justice Department could choose to appeal a ruling allowing Venezuela to fund Maduro’s defense, notwithstanding U.S. sanctions. Prosecutors would likely win – but the appeal itself would take months, and then Maduro would receive court-appointed counsel. That would effectively hit the reset button on the entire case, as new lawyers would need to start from scratch and get up to speed.
The Maduro case involves global stakes in its own right. And now the Trump administration apparently intends to use similar tactics elsewhere. Sarah Fitzpatrick of The Atlantic reports that “the U.S. attorney’s office in South Florida is preparing indictments against Cuba’s political and military leadership,” following the Maduro model of removal and prosecution of disfavored foreign heads of state.
Judge Hellerstein should have reassigned the Maduro case right away, and he still should reassign it now, though it’s clear he won’t. This bit of judicial self-indulgence, coupled with the excruciating pace and baffling nature of his decisionmaking, threatens to undermine the Maduro prosecution, and potentially others to follow. The world is watching, and it’s not looking good.
