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.