Now, at 92 years old, Hellerstein is presiding over the virtually unprecedented narcoterrorism case against ousted Venezuelan President Nicolás Maduro. The jurist is also overseeing President Trump’s continuing bid to move his hush-money case from state to federal court. Lawyers who have practiced before Hellerstein say he can be charming toward jurors but is tough on prosecutors and defense attorneys alike. For at least the past several years, lawyers say, he has appeared at times to nod off on the bench. (Lawyers and federal judges noted that Hellerstein is far from the only jurist to close his eyes—or even snooze—in court.)