Judge Overseeing Maduro Case Has Clashed Before With Trump Admin

The federal judge now overseeing the prosecution of captured Venezuelan strongman Nicolás Maduro has a long record of hostility toward President Donald J. Trump, raising fresh questions about impartiality as one of the most consequential international criminal cases in modern history unfolds in New York.

U.S. District Judge Alvin Hellerstein of the Southern District of New York—an appointee of President Bill Clinton—was assigned this week to preside over Maduro’s case following the Venezuelan leader’s dramatic capture by U.S. Special Forces. Hellerstein is no stranger to either Maduro or Trump, having ruled on matters involving both for more than a decade.

Maduro and his wife were seized early Saturday in Caracas during a U.S. military operation that reportedly disabled portions of Venezuela’s air defense systems before transporting the couple to New York. They now face sweeping federal charges related to narcoterrorism and international drug trafficking. The operation sparked immediate backlash from left-wing governments and European leaders. Brazil, Chile, Mexico, and Spain condemned the action as a “dangerous precedent for peace,” while Argentine President Javier Milei openly celebrated the collapse of a dictatorship.

Hellerstein has been involved in cases connected to Maduro since 2014, well before a superseding indictment in 2020 formally named the Venezuelan leader. On Monday, Maduro appeared before Hellerstein for the first time as the lead defendant, underscoring the judge’s long-running role in the case.

The assignment has drawn renewed attention to Hellerstein’s past clashes with President Trump—particularly during the politically charged “hush money” prosecution in New York. In that case, Hellerstein repeatedly rejected Trump’s efforts to move state criminal proceedings into federal court, ensuring the case remained under New York’s jurisdiction.

That prosecution centered on payments made by Trump’s former attorney, Michael Cohen, to adult film actress Stormy Daniels—whose legal name is Stephanie Clifford—shortly before the 2016 election. A state jury later convicted Trump, with Hellerstein playing a key role in blocking federal intervention.

“Reimbursing Cohen for advancing hush money to Stephanie Clifford cannot be considered the performance of a constitutional duty,” Hellerstein ruled at the time.

Following a 2024 Supreme Court decision that clarified presidential immunity standards, Hellerstein was ordered to reconsider aspects of his reasoning. The U.S. Court of Appeals for the Second Circuit likewise instructed the lower court to revisit the underlying arguments. Hellerstein ultimately doubled down.

“Falsifying business records to hide such reimbursement, and to transform the reimbursement into a business expense for Trump and income to Cohen, likewise does not relate to a presidential duty,” he wrote.

Beyond Trump-related cases, Hellerstein has also challenged executive authority in immigration matters tied to Venezuela. Last year, he issued a temporary restraining order blocking deportations of Venezuelan nationals in his district without additional due process, criticizing the federal government’s use of the Alien Enemies Act against suspected gang members.

Meanwhile, Maduro’s first appearance in an American courtroom reportedly stunned the former dictator. During the hearing, Maduro appeared visibly surprised when informed of the constitutional protections afforded to criminal defendants in the United States.

He indicated he had been unaware that he had the right to legal counsel, the right to remain silent, the ability to seek bail, and that statements made without an attorney present could be excluded from evidence.

The case has already sent shockwaves across Latin America. President Trump, speaking aboard Air Force One, escalated tensions by warning Colombian President Gustavo Petro that his days in power may be numbered.

“The government in Bogotá is run by a sick man who likes making cocaine and selling it to the United States,” Trump said. “And he’s not going to be doing it very long. Let me tell you.”

When asked whether that implied potential military action, Trump responded bluntly: “Sounds good to me.”

Secretary of State Marco Rubio added fuel to the fire, declaring that Cuba is “ready to fall,” just one day after U.S. forces captured Maduro in what officials have described as a decisive blow to narco-dictatorships in the region.

Petro responded angrily on X, calling Trump’s remarks “slander” and urging Latin American nations to unite or “be treated as servants and slaves.” He further accused Washington of bombing a South American capital “for the first time in human history” following what he described as the U.S. abduction of Maduro.

As Maduro’s case proceeds under a judge with a documented history of opposing President Trump, conservatives argue the stakes could not be higher—for American justice, executive authority, and the global fight against narco-terrorism.