Judge Alvin Hellerstein, a 92-year-old legal lion, is back in the spotlight with a case involving none other than former Venezuelan President Nicolás Maduro.

This veteran jurist from the U.S. District Court for the Southern District of New York is juggling high-stakes cases, from Maduro’s legal woes to past battles with former President Donald Trump over courtroom jurisdiction.

Hellerstein’s Long Tenure on the Bench

Appointed over 25 years ago by former President Bill Clinton at age 64, Hellerstein has seen it all. Now a senior judge, his courtroom in New York has become a battleground for cases involving powerful figures.

His history with heads of state isn’t new. Hellerstein has been handling matters tied to Maduro since 2014, long before the recent superseding indictment named the former Venezuelan leader in 2020.

Monday marked a milestone as Maduro appeared in Hellerstein’s court as the lead defendant for the first time. It’s a moment that underscores the judge’s knack for drawing cases that make headlines.

Trump’s Legal Defeats Under Hellerstein

Before Maduro, Hellerstein crossed swords with Donald Trump in the infamous “hush money” case. He repeatedly shot down Trump’s attempts to shift his New York State criminal proceedings to federal court.

That case centered on payments to Trump’s former attorney Michael Cohen, who shelled out money to adult film star Stephanie Clifford, known as Stormy Daniels, just before the 2016 presidential race. A state jury ultimately found Trump guilty, but Hellerstein’s rulings kept the fight in state hands.

Speaking of those rulings, Hellerstein didn’t mince words: “Reimbursing Cohen for advancing hush money to Stephanie Clifford cannot be considered the performance of a constitutional duty,” he declared. With all due respect, Judge, conservatives might argue this sidesteps the broader question of whether such personal matters should even be weaponized against a former president.

Presidential Immunity and Legal Wrangling

But the plot thickened when a 2024 Supreme Court ruling forced Hellerstein to revisit his stance on presidential immunity in Trump’s case. The U.S. Court of Appeals for the Second Circuit also ordered a reexamination of the arguments. It’s a reminder that even seasoned judges face pressure from higher courts.

Hellerstein doubled down in his critique, stating, “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.” Fair point on paper, but let’s not pretend this doesn’t smell like a progressive push to keep Trump tangled in legal knots.

Beyond Trump, Hellerstein’s docket includes other heavy hitters. In 2025, he oversaw the trial of Charlie Javice, convicted of defrauding JPMorgan Chase out of $175 million by inflating her company Frank’s customer base—a supposed game-changer for college financial aid.

Venezuelan Cases and Broader Implications

Closer to Maduro’s orbit, Hellerstein tackled a deportation case last year involving two Venezuelans. He granted a temporary restraining order to protect deportees in his district from removal without due process, challenging the use of the Alien Enemies Act against alleged gang members.

While some might cheer this as compassion, conservatives question if such rulings risk undermining strict immigration enforcement. It’s a fine line between due process and opening doors to policies that could strain local communities.

As Hellerstein continues to preside over Maduro’s case, his courtroom remains a lightning rod for controversy. From Trump to Venezuelan leaders, his rulings shape narratives that ripple far beyond New York. For conservatives, it’s a call to watch closely—justice must cut through political agendas, not cater to them.