A US federal judge who previously blocked attempts by the Trump administration to deport pro-Palestine students and activists is now presiding over the case of former Venezuelan president Nicolas Maduro, according to Israeli media reports.
Judge Alvin Hellerstein, 92, halted efforts last September to remove protesters who had demonstrated against Israel’s war on Gaza, ruling that the proposed deportations were unlawful.
Earlier in the year, he also blocked the same administration from expelling Venezuelans under the "Alien Enemies Act", finding that the law had been applied illegally.
Hellerstein did not rule on individual Palestinian activist cases, but blocked the administration’s broader use of emergency deportation powers without due process.
Israeli news site Ynet said the rulings placed Hellerstein on a collision course with President Donald Trump, adding that the resulting "tension" could shape proceedings in the Maduro case, which is being heard in New York’s Southern District.
Maduro, who until early Saturday was Venezuela’s president, was detained following what the report described as his capture by US Delta Force commandos. He is currently being held at Brooklyn’s Metropolitan Detention Centre (MDC), a facility that has drawn sustained criticism from judges, detainees, and human rights groups over its conditions.
Hellerstein will oversee the trial from a Manhattan courtroom.
Israeli media reports on Sunday described him as "no ordinary judge", noting that he leads a religious Jewish life, observes the Sabbath, and previously chaired The Jewish Centre, one of New York’s prominent Orthodox synagogues. According to the report, his routine includes regular prayer and long-standing tennis matches with fellow rabbis, during which legal and judicial discussions often take place.
Born in New York in 1933, Hellerstein studied law at Columbia University before serving in the US Army’s military prosecution service.
After decades in private legal practice, he was appointed a federal judge in 1998 by then US President Bill Clinton. He later became a central figure in the Southern District of New York, widely regarded as the most influential federal court in the United States due to its jurisdiction over Manhattan.
He has built a reputation as a cautious and exacting judge through his handling of major cases, including civil compensation claims brought by victims of the 11 September 2001 attacks, as well as complex corruption and financial crime cases.
In 2019, he presided over the civil lawsuit against film producer Harvey Weinstein, rejecting an initial settlement proposal.
Despite his religious background, Ynet reported that Hellerstein does not inject his religious affiliation into his rulings. In November, he sentenced an Israeli citizen named Olivier Omer after he was convicted of corruption as a senior executive at the startup Frank alongside its founder Charlie Javice.
Omer’s lawyers had sought a reduced sentence, arguing that his Jewish identity and Israeli nationality could expose him to risk in US prisons amid heightened anti-Zionist sentiment linked to the war on Gaza, but Hellerstein rejected the request, ruling that punishment could not be influenced by a defendant’s nationality or religion.
The judge has also drawn attention for rulings that constrained executive power. In addition to blocking deportations of pro-Palestine activists, he prevented the Trump administration last spring from expelling Venezuelans under emergency wartime legislation, finding the measure unlawful.
Maduro faces an indictment in New York that includes charges described as "narco-terrorism trafficking, weapons possession, and cocaine supply". He is being held at the MDC in Brooklyn, whose reputation has deteriorated to the point that federal judges have increasingly resisted sending detainees there.
In a recent case cited by Ynet, a judge blocked the transfer of a defendant accused of tax fraud to the facility, citing "dangerous, barbaric conditions", and referring to an incident in which a detainee was stabbed multiple times without receiving medical treatment while remaining in his cell for 25 days.
The detention centre has previously held several high-profile inmates, including Sean "Diddy" Combs, former cryptocurrency executive Sam Bankman-Fried, Ghislaine Maxwell, and singer R. Kelly. Human rights organisations have described the facility as a place that "breaks detainees’ spirits" even before trial.
According to Ynet, Maduro is expected to be held initially in solitary confinement before being transferred to a high-security wing, where he will await trial in what the site described as one of the most controversial cases in New York’s judicial history.