Clinton-appointed judge, 92, who ruled against Trump takes on Nicolas Maduro case

Judge Alvin K Hellerstein will oversee Nicolas Maduro’s New York case after his capture, having previously ruled against Donald Trump
Judge Alvin K Hellerstein handled several of Donald Trump’s personal legal battles between 2023 and 2024 (@rabbiefremgoldberg/Youtube)
Judge Alvin K Hellerstein handled several of Donald Trump’s personal legal battles between 2023 and 2024 (@rabbiefremgoldberg/Youtube)

NEW YORK CITY, NEW YORK: Judge Alvin K Hellerstein, a 92-year-old federal judge in New York, will preside over the criminal case against Venezuelan President Nicolas Maduro

US forces captured Maduro in a surprise military operation in Caracas early Saturday, January 3. He now faces federal criminal charges in New York City, including conspiracy to commit narco-terrorism and conspiracy to import cocaine, and is awaiting trial.

Former President Bill Clinton appointed Hellerstein in the 1990s, and he has continued handling major cases even after taking senior status. Hellerstein has issued several high-profile rulings against Donald Trump and his administration, including decisions on immigration policy.

Alvin Hellerstein's rulings against Trump

IN FLIGHT - JANUARY 04: U.S. President Donald Trump (R) and U.S. Sen. Lindsey Graham (R-SC) speak to the media aboard Air Force One enroute to Washington, DC on January 04, 2026. Trump is returning to the White House after giving the order for the United States law enforcement to capture Venezuelan President Nicolás Maduro and his wife. (Photo by Joe Raedle/Getty Images)
 President Donald Trump and Sen Lindsey Graham (R-SC) speak to the media aboard Air Force One enroute to Washington, DC on January 04, 2026 (Joe Raedle/Getty Images)

Judge Alvin Hellerstein has issued several controversial rulings against Donald Trump and his administration, covering Trump’s time as a private citizen, his first presidency, and his current second term.

In a case involving the prolonged detention of an asylum seeker, Hellerstein criticized the Trump administration and ruled that officials could not hold asylum seekers indefinitely without hearings. He wrote that “autocracies of the world have been marked by harsh regimes of exclusion and detention,” calling the policy unconstitutional and inhumane.

The judge ordered expedited reviews for detainees, directly challenging the Department of Homeland Security’s enforcement tactics. His strong language sparked controversy, with administration officials condemning it as judicial activism interfering with border security.

This ruling became part of a larger litigation track documenting over 100 challenges to Trump-era immigration policies, and Hellerstein’s order extended in subsequent updates.

CARACAS, VENEZUELA - NOVEMBER 21: President of Venezuela Nicolás Maduro speaks during a march as part of the
President of Venezuela Nicolas Maduro speaks during a march as part of the 'Venezuelan Student Day' at Miraflores on November 21, 2025 in Caracas, Venezuela (Jesus Vargas/Getty Images)

Hellerstein also ordered the release of Trump’s former attorney, Michael Cohen, who returned to prison after home confinement. 

The judge ruled that federal officials acted in “retaliation” against Cohen for planning a tell-all book criticizing Trump, violating Cohen’s First Amendment rights. Hellerstein highlighted that Cohen’s probation terms included a media gag, which he deemed unconstitutional.

When the House Financial Services and Intelligence Committees subpoenaed Deutsche Bank and Capital One for Trump’s personal and business financial records to investigate money laundering, foreign influence, and presidential ethics, Trump sued to block the subpoenas, claiming they lacked a legitimate legislative purpose and were overly broad. Hellerstein rejected Trump’s motion and allowed Congress to access the financial records.

Alvin Hellerstein's rulings in Trump's personal legal battles

Nicolas Maduro on board the USS Iwo Jima. (Trump Truth Social)
Nicolas Maduro on board the USS Iwo Jima (@therealdonaltrump/Truth Social)

Judge Alvin Hellerstein, who handled several of Trump’s personal legal battles between 2023 and 2024, rejected Trump’s motion to move the hush-money case from New York state court to federal court.

The case involved allegations of falsified business records linked to payments to film actress Stormy Daniels. Hellerstein ruled that the case concerned Trump’s personal matters and was unrelated to his official duties as president. He described the case as focused on a private matter rather than presidential conduct.

After Trump’s conviction in the case and the Supreme Court’s ruling on presidential immunity, Hellerstein again denied a request to transfer the case, stating that the court’s immunity decision did not change his view that the acts were unofficial. He also noted that Trump had not shown sufficient cause for filing the request late, clearing the way for sentencing.

In a separate ruling, Hellerstein issued a temporary restraining order to stop the deportations of two Venezuelan immigrants without notice or hearings. He found that the Trump administration’s use of the 1798 Alien Enemies Act in this instance violated due process.

The Act had been invoked against members of the Tren de Aragua gang and was challenged by the ACLU. Hellerstein focused on providing immediate protections for detainees in New York, without ruling on the overall legality of the Act.

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