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The judge who was assigned to depose Venezuelan Nicolas Maduro’s case in the Southern District of New York has a history of clashing with President Donald Trump, according to reports this week. U.S. District Judge Alvin Hellerstein, who was appointed decades ago by then-President Bill Clinton, also has a history of dealing with the now-former dictator.
The Venezuelan leader and his wife were seized early Saturday by U.S. Special Forces in Caracas and flown to New York, where they face narcoterrorism and drug-trafficking charges. The operation, which disabled parts of Venezuela’s air defenses, came under immediate international fire. Brazil, Chile, Mexico, and Spain called it a “dangerous precedent for peace,” while Argentina’s Javier Milei praised the fall of a dictatorship.
Hellerstein has overseen matters involving Maduro since 2014, years before a superseding indictment in 2020 named the former Venezuelan leader. On Monday, Maduro appeared in Hellerstein’s courtroom for the first time as the lead defendant, a development that highlights the judge’s history of presiding over high-profile cases.
Hellerstein previously clashed with Donald Trump during the high-profile “hush money” case, repeatedly rejecting Trump’s efforts to move his New York state criminal proceedings into federal court.
The case focused on payments involving Trump’s former attorney, Michael Cohen, who paid adult film actress Stormy Daniels, whose legal name is Stephanie Clifford, shortly before the 2016 presidential election. A state jury later convicted Trump, while Hellerstein’s rulings ensured the proceedings remained in state court.
“Reimbursing Cohen for advancing hush money to Stephanie Clifford cannot be considered the performance of a constitutional duty,” he declared at the time.
The case took a new turn after a 2024 ruling by the Supreme Court of the United States required Hellerstein to reconsider his position on presidential immunity in Donald Trump’s case. The U.S. Court of Appeals for the Second Circuit also directed the court to reexamine the underlying arguments.
That led Hellerstein to respond: “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.”
Closer to Maduro’s orbit, Hellerstein last year presided over a deportation case involving two Venezuelan nationals. He issued a temporary restraining order barring removals without due process for detainees in his district, calling into question the government’s use of the Alien Enemies Act against individuals accused of gang affiliation.
Maduro, meanwhile, appeared visibly surprised Monday after learning of the constitutional rights afforded to criminal defendants in the American legal system during his first court appearance.
During the hearing, Maduro indicated he was previously unaware that he was entitled to legal counsel, had the right to remain silent, could seek bail, and that statements made outside the presence of an attorney could be excluded from evidence.
Trump has since threatened Colombian President Gustavo Petro with possible military action, while Secretary of State Marco Rubio declared that Cuba is “ready to fall,” just a day after U.S. forces captured Maduro in a surprise raid.
Speaking aboard Air Force One, Trump accused Petro of overseeing a “sick country” driven by cocaine exports and warned his rule would not last long.
“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 pressed if that meant military action, Trump replied, “Sounds good to me.”
Petro shot back on X, denouncing Trump’s remarks as “slander” and urging Latin America to unite or “be treated as servants and slaves.” He accused Washington of bombing a South American capital “for the first time in human history” following the U.S. abduction of Maduro.
